What happens when a suburban L.A. person dates a born-and-bred New Yorker? Well, for Kylie Jenner, that means getting coaxed out of her Range Rover–size comfort zone. Calabasas residents like Jenner are typically glued to their cars, but Hell's Kitchen natives like Timothée Chalamet certainly know how to get around without four wheels. In New York City today, Jenner and Chalamet opted for one particularly popular mode of public transportation: Citi Bikes.

Now, you didn't think Jenner would wear just anything on a Citi Bike, did you? Of course not! She wore the most fashion-person shoe choice imaginable: Maison Margiela Tabi Ballerina Flats ($1050). A genius decision really. The shoes are practical enough for pedaling yet still true to her luxe personal style. She styled the shoes with her favorite Guizio Perfect Classic Tank Top ($38), a pair of cropped black pants, and Otra Eyewear Kenny Sunglasses ($65). Scroll down to see Jenner's version of a bike-ride outfit in New York City.

On Kylie Jenner: Maison Margiela Tabi Ballerina Flats ($1050); Guizio Perfect Classic Tank Top ($38); Otra Eyewear Kenny Sunglasses ($65).

Shop Kylie Jenner's Exact Pieces

It's been an exciting few days for fans of the New York Knicks with the storied team going off in the playoffs and finalizing a sweep of the Cleveland Cavaliers in the Eastern Conference Finals last night to send it to its first NBA Finals in 27 years. Clearly, the players remember what happened last year—when they lost in Game 7 of the Eastern Conference Semifinals to the Indiana Pacers—and came prepared to right that wrong in dominant fashion. It was a team effort, and six players scored in double digits, resulting in a whopping 37-point triumph inside the Cavs' home gym.

I would hate to take away from the team's victory, but as a fashion person, it's my duty to point something out. Sure, the Knicks may have prevailed on the court—quite glaringly, I might add—but the real winner of the Eastern Conference Finals sat a few steps away from the actual basketball action. I am indeed talking about Kylie Jenner's black crocodile Chanel tote, which the A-lister—sat beside her boyfriend, Timothée Chalamet—wore with a vintage Knicks T-shirt, a leather jacket, Levi's jeans, and a pair of heeled thong sandals.

Kylie Jenner's Courtside Look

On Kylie Jenner: Chanel bag; Levi's jeans; The Row shoes

The bag designed by the French house's creative director, Matthieu Blazy, is one of many that have gone viral since Blazy's debut back in October. Called the Small Shopping Bag, it is currently available in two versions: a mint option made of crocodile-embossed calfskin and a classic calfskin leather option in rich burgundy. They retail for $7300 and $7000, respectively. Naturally, Jenner's isn't available, at least not yet. A new fuchsia option is on its way for fall/winter 2026, according to the runway show, but so far, black hasn't hit the runway. Leave it to her, though, to snag an exclusive colorway and wear it casually with a graphic tee and jeans for a basketball game—iconic.

Prepare for more courtside looks starting on June 3, which is when the Knicks will take on either the San Antonio Spurs or the Oklahoma City Thunder, a game that Jenner and Chalamet will no doubt be attending.

Shop Chanel's Small Shopping Bag

When the history books record the events of 2025, there will undoubtedly be a great deal to chronicle. But when it comes to the fashion of the time, it’s safe to say that no one did it better this year than the array of best-dressed celebrity couples of 2025. This year, unlike any other that has come before it, has been a watershed moment for the stars who remain true to the adage that dressing together means you stay together.

Hollywood is certainly no stranger to pairings who prop one another up via stunt dressing (Britney Spears and Justin Timberlake’s matching denim outfits at the 2001 American Music Awards), bold sartorial swings (Pamela Anderson’s pink fluffy hat and Tommy Lee’s Burberry trench coat at the 1999 VMAs) or entirely harmonious ensembles (Zendaya and Tom Holland’s twinning burgundy looks for an evening out in NYC in 2024).

Yet, in 2025, it appears that couples dressing in all its forms has never been more popular. It’s not just a case of copying exactly what your partner was wearing, despite there being a lot of that over the last twelve months, or stepping out in something so polar opposite to your significant other that you stoke ire. No, instead, 2025 was a year where couples honed their public image through the garments they wore.

As always, there are couples who did this well, and couples where this attempt to cement themselves in the mainstream through clothing certainly slightly backfired. Ultimately, what was gleaned this year is that couples dressing isn’t just about making us covet the person they’re with. Instead, it’s about coveting the wardrobes they share. So, without further ado, uncover the 11 best-dressed celebrity couples for 2025 ahead.

The 11 Best-Dressed Celebrity Couples of 2025

1. Kylie Jenner and Timothée Chalamet

Style Notes: At the tail end of 2025, Timothée Chalamet delivered the most romantic public display of affection for Kylie Jenner: Dedicating a verse to her on his remix of Liverpool-based rapper EsDeeKid’s single “4 Raws”. This cultural moment came on the heels of a mammoth press tour in the lead-up to the release of A24’s Marty Supreme, a new kind of sports drama that sees the Academy Award-nominee lead Josh Safdie’s first solo film as a director as a fictionalised version of New York table tennis champion Martin Reisman. Part of the promotional run saw Chalamet and Jenner take couple dressing to new heights by showing up to the movie’s Los Angeles premiere in matching ping pong ball tangerine-coloured sets from Chrome Hearts. Giving Hermes orange a run for its money, the outing not only marked a major step in the couple’s relationship, but also an incredible entry in the annals of pop culture. The couple began the year with a slew of red carpet appearances at Hollywood’s biggest events, including the Oscars and Golden Globes, so, ending it with an excursion so dramatic as this only feels right.

Shop the Outfits:

2. Zoë Kravitz and Harry Styles

Style Notes: Despite only being together for a few months, Zoë Kravitz and Harry Styles have made their romance more akin to a jet-setting spectacular than anything else. Whilst the best-dressed celebrity couples would traditionally utilise the step-and-repeat to display their complementary style, Kravitz and Styles have gone the opposite route, opting for more quotidian and quieter showcases that position themselves as the most relatable stars yet; regular, familiar and domestic. From the concrete avenues of New York to the cobblestone streets of Rome and the gateways of Berlin, the actress and the singer have provided nothing short of a masterclass in a shared wardrobe along every stop of their international affair. Of course, when your closets both heavily feature pieces from luxuriates like The Row, sharing is certainly always caring.

Shop the Outfits:

3. Rihanna and A$AP Rocky

Style Notes: Six years, three children, and one nuptials-themed music video later, A$AP Rocky and Rihanna are stronger than ever. On a romantic level, this is certainly true, but when it comes to the couple’s sartorial liaisons, it could not be more fitting. The couple began by presenting their approach to trail style with impeccable tailoring and matching suits before taking things to the red carpet for the ultimate bad girl’s return to the screens with Smurfs. She might’ve been lending her voice to a children’s film, but she didn’t let her little blue persona stop her from wearing masterpieces from Chanel, Saint Laurent, Alaia and more. (The Fenty Beauty founder also dressed her sons in miniature versions of Jonathan Anderson’s debut menswear collection for Dior for the occasion.) Later, she welcomed the couple’s daughter, Irish Rocky Meyers, dripping in an Audemars Piguet Royal Oak rose gold watch valued upwards of £25,000. Then, to conclude the year, they took to the awards season circuit to promote the rapper’s role in Spike Lee’s crime thriller Highest 2 Lowest. See: A custom pink Balenciaga ball gown and feathered hat for her, and a Mattieu Blazy for Chanel three-piece for him.

Shop the Outfits:

4. Victoria Beckham and David Beckham

Style Notes: From Posh and Becks to Sir David and Lady Victoria. Oh, how time flies. With the couple celebrating their 26th wedding anniversary earlier this year, the couple’s approach to dressing is proof that good things come with age. They might’ve shed their harmonious purple bridal outfits, WAG-era micro denim shorts and pop star leather looks for something more demure, but they still will always deliver an ensemble worth taking note of. Case in point: The monochromatic silhouettes for the premiere of Victoria’s self-titled Netflix docuseries, the soiree-ready pieces for the former footballer’s 50th birthday and the regal regalia donned for David’s investiture ceremony as a knight back in November.

Shop the Outfits:

5. Lana Del Rey and Jeremy Dufrene

Style Notes: Throughout Lana Del Rey’s entire discography, you can find depictions of great love stories soundtracked to her signature melancholic and diaristic sonic landscape. How fitting then, that in 2024, the songstress made her own entry into this canon of eminent American romances by wedding Cajun swamp tour boat operator, Jeremy Dufrene. She sings on sold-out tours at iconic venues and music festivals. He takes tourists and locals out to alligator swaps in the Louisiana bayou. As a result, their style couldn’t be more disparate. But it’s this discordance that makes them all the more compelling as a couple. Back in September, the newlyweds proved this point entirely when they attended Alessandro Michele’s most recent collection presentation as creative director of Valentino during the spring/summer 2026 season of Paris Fashion Week. The Grammy Award-nominated artist looked like a vision of Vivien Leigh in a dusty lilac dress featuring faux-fur straps, while her husband looked totally himself and straight out of the Mississippi Delta, complete with a baseball cap and upside-down Oakleys. As she told W Magazine what he would say to her: “You be you—and I’ll just love you more.”

Shop the Outfits:

6. Hailey Bieber and Justin Bieber

Style Notes: Appearing on every best-dressed couples list since they started dating in 2015, Hailey and Justin Bieber have been a fashion fixture for ten years in a row. This year, however, marked a new chapter for the pair. Mr Bieber returned to the studio with back-to-back releases featuring crooning ballads to his wife. (“Daisies” and “Yukon”, to name a few.) Mrs Bieber became a billionaire after selling her skincare empire, Rhode Beauty, to e.l.f Cosmetics and launching into Sephora nationwide across the US and UK. Together, they celebrated the first birthday of their nepo baby scion, Jack Blues. Doing it all with style, albeit a topic that’s still somewhat controversial even a decade on, every date night or public appearance was a display of their unharmonious dress sense. Still, we wouldn’t change it for the world. Because who else can give us an oversized leopard print coat and mini dress alongside a baggy hoodie and track pants?

Shop the Outfits:

7. Kaia Gerber and Lewis Pullman

Style Notes: Kaia Gerber’s relationship history has always seen her on the side of burgeoning members of Young Hollywood. But as a supermodel, nascent actress and bibliophile in her own right, the star has come into her own in 2025. Doing so, she stepped out with a new beau, actor Lewis Pullman, bringing her newfound sense of assuredness, maturity and elegance to their couple's dressing. At the 2025 Venice Film Festival, the duo hard-launched their relationship with several sights across the picturesque canals. Doing so in Sarah Burton’s creations for Givenchy, balmy pieces from Australian resortwear brand With Jéan and eyewear from Khaite’s collaboration with Oliver Peoples, the new era marked a confident and refined approach to fashion that marked this new stage in her career and courtships.

Shop the Outfits:

8. Margaret Qualley and Jack Antonoff

Style Notes: Following their casual 2023 wedding on the New Jersey coastline, Margaret Qualley and Jack Antonoff have remained a mainstay within the industry. Now, riding on the success of The Substance and following on from the release of Honey Don’t, the Chanel actress has shed any remnants of her young, ingénue persona with more theatrical and striking ensembles that reflect her flourishing career. In custom creations from Virginie Viard and Mattieu Blazy, Qualley has embodied modern glamour and heavenly beauty in every step. For his part, the acclaimed music producer has stayed true to his North Eastern roots with loose tailoring and oversized shapes.

Shop the Outfits:

9. Paul Mescal and Gracie Abrams

Style Notes: Paul Mescal and Gracie Abrams officially went public with their relationship on the fields of Somerset following a five-day stint at Glastonbury. With it, their hard-launch brought a revived appeal for bandanas, loose maxi dresses and a music festival Instagram dump. Despite maintaining their privacy, this rare glimpse into their relationship, and consequent couple style, was one that merited the wait. In matching Adidas trousers—three-inch inseam shorts for him and three-stripe trackpants for her—skin-tight white t-shirts and nonchalant accessories, the couple proved that despite their rare outings together, there is nothing overstyled or finicky about them. Normal people, indeed.

Shop the Outfits:

10. Dua Lipa and Callum Turner

Style Notes: Dua Lipa and Callum Turner stay booked and busy. As the songstress said in a recent Instagram post, the passport stays packed, meaning that any street corner, new destination or exotic locale could serve as a backdrop for their couple dressing. Aside from Lipa’s global stadium tour that saw them visit Australia, Brazil and Mexico (to name a few), the couple spent most of their downtime close to home in Hampstead Heath. Both raised in London, their style borders on some of the more experimental and street-focused than any other couple on this list. Never one to shy from an independent designer, small brand or British label, the couple are the definition of hometown pride.

Shop the Outfits:

11. Leighton Meester and Adam Brody

Style Notes: He might appear on the award-nominated show Nobody Wants This, but when it comes to the couple style between Leighton Meester and Adam Brody, that adage couldn’t be further from the truth. Both breaking through to mainstream success with teen dramas in the early 2000s (Gossip Girl and The O.C., respectively), the married couple feels like a marker of a different time in Hollywood. Rather than gushing social media carousels and regular sightings at trending restaurants across Los Feliz and Silver Lake (an homage to Meester’s role on Rachel Sennott's now-titled HBO series I Love LA), we instead get glimpses of them when out on the red carpet at industry events. Wearing designers like Prada, Versace and Jaquemus might also heal our inner teenagers, because Seth Cohen and Blair Waldorf, forever.

Shop the Outfits:

Who was your best-dressed celebrity couple for 2025? Let us know in the poll, below!

Why Trust Us

At Who What Wear UK, fashion is our speciality. Our editors have years of industry experience, from reporting on seasonal fashion trends seen at international fashion weeks to working with some of the most recognisable names in fashion. Every item we recommend is carefully selected based on current trends, quality and real-world wearability.

We regularly try on pieces ourselves—everything from best-selling jeans to designer shoes—and speak to external experts and fashion insiders, staying closely connected to what our readers are searching for. Our advice is grounded in expertise, and each and every buy we feature has to meet our exceptional taste standards—so you can feel confident in every recommendation.

Welcome to The Who What Wear Podcast. Think of it as your direct line to the designers, stylists, beauty experts, editors, and tastemakers who are shaping the fashion-and-beauty world. Subscribe to The Who What Wear Podcast on Apple Podcasts and Spotify.

On the latest episode of The Who What Wear Podcast, I'm joined by Arianne Phillips, the costume designer of A Complete Unknown. She told me the backstory behind some of Timothée Chalamet's 67 costumes, which required more fittings than she's ever done for any movie she's worked on (including Don't Worry Darling, Once Upon a Time in Hollywood, and Walk the Line).

Phillips discussed how her costumes reflected Bob Dylan's style evolution, which went from baggy jeans and workwear shirts in the early '60s to fitted blazers, skinny jeans, and sleek Chelsea boots just a few years later. Phillips also revealed where she sourced Chalamet's sunglasses and the special jacket worn by Elle Fanning in the film. Scroll down for excerpts from the interview.

What was your experience working with Timothée Chalamet?

Being a costume designer, we are the only department that says, "Hello, nice to meet you. Take your clothes off." It's a very intimate job, and we're often the first person that the actor meets before shooting. That first day we met, it's really about building trust, and I believe that my job is helping them visually with research. Timmy had been really, really focused with [director James Mangold] on the script, the acting, the singing, and the music. He learned piano, acoustic and electric guitar, and harmonica, so he had his hands full for quite a while. He was a wonderful scene partner for me in terms of his enthusiasm and his sense of focus.

We had to do many fittings. I probably did more fittings on this movie than I've ever done because of the way that we were telling this story through time. Working with Timmy was a dream. He's incredibly open and curious—which are always my favorite qualities in an actor—and very, very collaborative. He was really up for everything and patient. You know, it takes a lot of patience to do fittings. We have to prick and prod and try things that maybe never work. We have to turn over every stone to make sure we're making the right choices.

I'd love to talk about Bob Dylan's sunglasses. Can you discuss the symbolism of these accessories and where you sourced them?

The sunglasses provide a veneer and a separation from the bright lights and the fandom that he was largely uncomfortable with. The sunglasses are Bausch & Lomb, which is a very early iteration of Ray-Ban. There's a wonderful business here in Los Angeles that supplies vintage glasses, optical and sunglasses, called Old Focals. I went to [the owner Russ Campbell] immediately. He knew exactly what sunglasses [Bob Dylan wore], and we just had to figure out what was right for Timmy's face.

I really learned a lot about Bob Dylan's style in 1965. When he went to London on tour, he clearly came back with Chelsea boots and skinny jeans. His hair got longer. His sunglasses got more angular. He was a huge fan of The Beatles, and he was hanging out with them and Donovan, and you can see that early mod style that he adopted in 1965. The sunglasses are definitely part of that rock and roll archetype that is so iconic.

Where did you source the traditional Romanian coat that Elle Fanning wears in the film?

I personally didn't want to use real fur, which Bob probably wouldn't have been able to afford at that time anyway. It took quite a while to source that coat. We got it from a vintage dealer on Etsy. That was one of those gems that we were able to find, but most of Timmy's costumes were made. There are a few vintage pieces that are always important, I think, especially because you just can't re-create the hang and the feel of that fabric and sometimes the patterns.

For the second year in a row, Kylie Jenner managed to sneak past the photographers outside the Golden Globes and into the award ceremony to accompany Timothée Chalamet for a star-studded night out. Last time around, she surprised the internet when she skipped the red carpet and showed up at Chalamet's table wearing a completely sheer vintage gown by Hanae Mori with a low, ruffled back and long sleeves. This year, she followed suit with an even bolder and, dare I say, iconic ensemble.

Though no full-body photos have surfaced of Jenner's look at this year's Golden Globes (yet!), we have secured a few angles of her dress in candid photos of her sitting with Chalamet as well as group shots with his A Complete Unknown co-stars Monica Barbaro and Elle Fanning, both of whom also sat at their table, and Fanning's sister Dakota. The Kylie Cosmetics founder chose a vintage chain mail–like dress with thin straps, a cowl neckline, and a low, scooped back that was decorated with what appears to be floral embroidery. She pulled it from Versace's archives, specifically the S/S 99 collection. It's even older than the dress it made me think of immediately—one worn over 20 years ago by another Hollywood sensation.

If our minds think alike, then you already know who wore it: Paris Hilton. The Julien Macdonald dress was worn to Hilton's 21st birthday party in London in May 2002 and featured the same cowl neckline, thin straps, and shockingly low back. It's hard to tell the length of Jenner's dress from the photos available, but if it turns out to be mini, then it truly is a perfect modernized take on Hilton's incredible Y2K party dress.

Scroll down to see Jenner's dress from every angle.

One of the best things about the awards season is that there's always sure to be something that takes you by surprise—e.g., one project could secure every single award or drama that ensues backstage (or sometimes onstage). But for Who What Wear editors, what always keeps us on our toes comes back to the moment when celebrities step onto the red carpet. We never know what people will wear, what trends will emerge, or what red carpet-looks will go viral. Sadly, though, in recent years, we've been in a bit of a dry spell when it comes to awards show style that, well, surprises. 

Don't get us wrong, we will always love a pretty red carpet look, but there's something to be said about those willing to take risks, especially when you're dressing up for an event as formal as the Golden Globes. It seems that so many celebrities are worried about whether they'll land on the "best dressed" list that they forget to enjoy the getting dressed-up part. However, that wasn't the case with one star this year: Kylie Jenner. While one might argue she wasn't necessarily "fully dressed" (wait until you see her ultra-sheer lace gown), nonetheless, her presence was a welcome shift from the sea of cliché gowns. 

Many did not know Jenner would be in the audience at the Golden Globes since she did not walk the red carpet. However, she was there during the ceremony to support her beau, Timothée Chalamet, which quickly captured the attention of the internet. Although most of the buzz did surround the on-screen kiss they shared, we were more enthralled with their looks for the evening. Frankly, you won't blame us once you see them for yourselves! Keep scrolling to see what Chalamet and Jenner wore to the Golden Globes... 

Before we get to Miss. Jenner's look for the evening, we must at least acknowledge the man of the evening: Chalamet. Garnering his third Golden Globe nomination, the actor was up for the category "Best Performance by an Actor in a Motion Picture" for the film Wonka. Chalamet chose to celebrate the occasion by wearing head-to-toe Celine Homme by Hedi Slimane. He might not have won the globe this evening, but this look was a winner in our books. Plus, he got to snuggle up with Jenner for the evening, which who wouldn't want to after seeing her look? 

Jenner might have skipped the Golden Globes red carpet, but make no mistake, she still served a look. Donning a vintage piece by Hanae Mori, the sheer lace floor-length gown featured long sleeves and a ruffled low-back. Jenner kept the rest of the look minimal with neutral-hued nails, a nude lip, and very little jewellery, allowing the dress to be the focal point of the evening—boy was it just that. 

Despite Jenner's attendance being a surprise to the world, it further cemented the couple's status. They successfully honoured their own style through each of their Golden Globes looks while complimenting each other sublimely. As with most celebrity couples, there comes a point where we think we've seen it all, but these two continue to surprise and delight us. 

Shop the Sheer Dress Trend

Next Up: The Most Jaw-Dropping Golden Globes Red Carpet Looks

This post originally appeared on Who What Wear US. 

One of the best things about the award season is that there's always sure to be something that takes you by surprise—e.g., one project securing every single award or drama ensuing backstage or sometimes onstage. For Who What Wear editors, what always keeps us on our toes comes back to the moment when celebrities step onto the red carpet. We never know what people will wear, what trends will emerge, or which red carpet looks will go viral. Sadly, though, we've been in a bit of a dry spell when it comes to award show style that, well, surprises. 

Don't get us wrong. We will always love a pretty red carpet look, but there's something to be said about those willing to take risks, especially when you're dressing up for an event as formal as the Golden Globes! It seems that so many celebrities are worried about whether they'll land on a best dressed list that they forget to enjoy the "getting dressed up" part. However, that wasn't the case with one star this year: Kylie Jenner. One might argue she wasn't necessarily fully dressed. (Wait until you see her ultra-sheer lace gown.) Nonetheless, her presence was a welcome shift from the sea of cliché gowns. 

Many did not know Jenner would be in the audience at the Golden Globes since she did not walk the red carpet. She was there during the ceremony to support her beau, Timothée Chalamet, which quickly captured the attention of the internet. Although most of the buzz did surround the on-screen kiss they shared, we were more enthralled with their looks for the evening. Frankly, you won't blame us once you see them for yourselves! Keep scrolling to see what Chalamet and Jenner wore to the Golden Globes.

Before we get to Jenner's look for the evening, we must acknowledge the man of the evening. Garnering his third Golden Globe nomination, Chalamet was up for the Best Performance by a Male Actor in a Motion Picture award for the film Wonka. Chalamet chose to celebrate the occasion by wearing head-to-toe Celine Homme by Hedi Slimane. He might not have won the globe this evening, but this look was a winner in our books. Plus, he got to snuggle up with Jenner for the evening—who wouldn't want to after seeing her look? 

Jenner might have skipped the Golden Globes red carpet, but make no mistake. She still served a look. A vintage piece by Hanae Mori, the sheer lace floor-length gown featured long sleeves and a ruffled low back. Jenner kept the rest of the look minimal with neutral-hued nails, a nude lip, and very little jewelry, allowing the dress to be the focal point of the evening.

Despite Jenner's attendance being a surprise to the world, it further cemented the couple's status. They successfully honored their own style through each of their Golden Globes looks while complementing each other sublimely. As with most celebrity couples, there comes a point where we think we've seen it all, but these two continue to surprise and delight us. 

Shop Pieces Inspired by Jenner's Look

Leave it to Timothée Chalamet to turn heads wearing the most accessible A-list attire we've seen all summer. By now, we know the Wonka star is always one to watch for gender-bending looks on the red carpet, but his street-style chops are heating up, too. 

The swoon-worthy Chalamet was spotted in SoHo, New York, casually clad in black cargo shorts, a long-sleeve black shirt, blue Commes de Garçons x Converse high-top sneakers, and a NY Rangers baseball cap. We must admit that this guy has range since he wore Converse to the Met Gala, too.

Ahead shop 11 styles of the Commes des Garçons x Converse shoes available now. Remember, they're listed in men's sizes but are unisex. And, at $150, we won't blame you for buying a few different pairs. After all, they're Timmy-approved as everyday and special-occasion attire. 

On Timothée Chalamet: Commes des Garçons Play x Converse Hidden Heart High-Top Sneakers ($150)

Shop More Commes de Garçons Play x Converse Sneakers

Next, 15 Viral Shoe Trends That Are Already Defining Summer 2023

Awards season is back, and the jewel in its crown—the Oscars—is upon us. Sure, most of us night spend our days in sweatpants and jeans, but we’re looking forward to the sartorial escapism that the Oscars red carpet will bring this year. 

Since 1929, the Academy Awards has maintained firm footing in the zeitgeist not only by being a point of contention and conversation but also for history-making moments, including some of the best red carpet looks of all time. While some years are more memorable than others, we prefer to focus on the standout moments that made us smile. Sequins, satin, and sleeveless dresses may be timeless, but the best Oscars looks of all time aren’t always the safest bet—they’re daring, bold, and sometimes deemed "the worst” at first, but that’s what makes them iconic. Ahead, you’ll find the 49 Oscars looks that surprise and delight and that were truly indicative of the times.

WHO: Audrey Hepburn and Jean Hersholt

WHAT: 1954 Academy Awards

WEAR: On Audrey Hepburn: Givenchy gown 

Oscars night 1954 was a major moment for Audrey Hepburn—not only did she win the Best Actress award for her breakout role in Roman Holiday, but it’s also worth noting that her custom-made Givenchy gown ushered in a new era in fashion. Hailed as one of the most classic dresses of the 20th century, this dress was indicative of Hepburn’s role as muse to French designer Hubert de Givenchy, and their relationship went on to change the way celebrities and designers worked together.

WHO: Grace Kelly and Edmond O'Brien

WHAT: 1955 Academy Awards

WEAR: On Grace Kelly: Edith Head gown and coat

It doesn’t get more glamorous than the future princess of Monaco, award-winning actress Grace Kelly. While she served quite a few iconic looks on- and off-screen, her custom-made Edith Head gown was her most iconic red carpet outfit for several reasons: That night, she took home the award for Best Actress (in the film The Country Girl), and it was one of the most expensive dresses worn to the ceremony, crafted from £3500 worth of French satin.

WHO: Elizabeth Taylor

WHAT: 1957 Academy Awards

WEAR: William Ruser tiara and earrings

Yes, gowns are an essential part of making the Oscars a true Hollywood affair, but let’s be honest: The jewellery really makes the night sparkle. No one quite knew the power of jewels like actress Elizabeth Taylor. After all, who else could pull off wearing a full-diamond tiara to the Academy Awards?

WHO: Barbra Streisand

WHAT: 1969 Academy Awards

WEAR: Arnold Scaasi jumpsuit

Long before naked dresses and sheer jumpsuits were a thing, Barbra Streisand turned heads with her transparent jumpsuit at the 1969 Academy Awards. Of course, the subtly sheer number was enhanced by the spotlights, but Streisand's star power—including taking home her first statue that night—was anything but accidental. 

WHO: Cher and Sonny Bono 

WHAT: 1973 Academy Awards 

WEAR: On Cher: Bob Mackie two-piece gown

Any Cher fan knows that she’s spent the duration of her career serving up iconic looks (she pioneered the naked-dress trend), but none are seared into our brains quite like her 1973 Oscars look. This stunning sequinned two-piece Bob Mackie gown is the stuff of psychedelic ‘70s dreams—not to mention, she looks fantastic. Cher, please drop the core workout routine.

WHO: Farrah Fawcett and Marcello Mastroianni 

WHAT: 1978 Academy Awards 

WEAR: On Farrah Fawcett: Stephen Burrows gown 

Farrah Fawcett’s slinky, gold Stephen Burrows gown rivals an Oscar statue itself.

WHO:  Diana Ross and Ernest Thompson 

WHAT: 1982 Academy Awards

WEAR: On Diana Ross: red sequin gown; white fur stole

If you’re coming out to the Oscars, you want to go all the way out. In the ‘80s, no one quite brought the glamour like singer and actress Diana Ross. This head-to-toe red sequinned gown is everything.

WHO: Whoopi Goldberg

WHAT: 1991 Academy Awards 

WEAR: black sequin column dress; pearl necklace and earrings

There are very few artists in the world who have won an EGOT—Whoppi Goldberg is one of them. Goldberg is the first-ever African American to be nominated for Best Actress and Best Supporting Actress (which she won in ‘91 for her performance in Ghost). Her look for the 1991 Academy Awards encompassed the type of popular sequinned column dresses that were everywhere during the late ‘80s and early ‘90s, making it historic in and of itself.

WHO: Madonna and Michael Jackson

WHAT: 1991 Academy Awards 

WEAR: On Madonna: Bob Mackie gown; Harry Winston diamond necklace and earrings 

Sooner or later, when it comes to rounding up a list of iconic red carpet looks, you have to include Madonna. Her ‘91 Oscars outfit was one for the history books, as she channeled Marilyn Monroe with a sequinned sweetheart-neckline Bob Mackie gown and £18 million worth of Harry Winston jewellery. Material girls, this is your look.

WHO: Sarah Jessica Parker and Matthew Broderick 

WHAT: 1993 Academy Awards 

WEAR: On Sarah Jessica Parker: brown sequin gown; blue-lens sunglasses 

Don’t get it twisted. Long before serving iconic on-screen looks as Carrie Bradshaw in Sex and the City, Sarah Jessica Parker was giving us head-to-toe ‘fits. Case in point: the simple yet very ‘90s brown sequin gown and blue-lens sunglasses she wore to the Academy Awards in 1993. 

WHO: Vanessa L. Williams 

WHAT: 1995 Academy Awards 

WEAR: sequin and mesh gown; pashmina; clutch bag

Remember the chocolate-brown, sequin, and mesh number Vanessa L. Williams wore in ‘95? The gown—with its multiple fabrics, colour, and cut—was far ahead of its time and includes almost every ‘90s trend we hold dear today.

WHO: Naomi Campbell

WHAT: 1996 Academy Awards

WEAR: yellow gown; diamond choker

Honestly, is it even a roundup of the best red carpet looks of all time without Naomi Campbell? What’s great about her 1996 Oscars look is the sheer understated elegance of it—the yellow floor-length gown with the halter cut paired with a diamond choker necklace is just too good for words.

WHO: Jada Pinkett Smith and Will Smith 

WHAT: 1997 Academy Awards 

WEAR: On Jada Pinkett Smith: two-piece Versace dress

Although this coordinated red carpet look from Jada Pinkett Smith and husband Will Smith may have been questionable at the time, it’s now a secret iconic gem. Not only was her vibrant green two-piece gown Versace, but the midriff-bearing look was also very indicative of the trends to come that would influence the future of all "risqué” red carpet looks.

WHO: Nicole Kidman and Tom Cruise 

WHAT: 1997 Academy Awards 

WEAR: On Nicole Kidman: Christian Dior Couture gown

When we think of the Oscars today, we think of couture, but that wasn’t the standard in 1997. Nicole Kidman’s stunning yellow Christian Dior Couture gown put newly appointed John Galliano on the map and couture on the carpet, elevating both the fashion industry’s profile in Hollywood and the Oscars red carpet for years to come.

WHO: Gwyneth Paltrow

WHAT: 1999 Academy Awards 

WEAR: Ralph Lauren ball gown; Harry Winston diamond necklace and earrings 

At the time of their debuts on the carpet, many of the most iconic Oscar looks were met with either fanfare or outright disgust. For Gwyneth Paltrow’s 1999 bubblegum-pink Ralph Lauren gown with £140,000 worth of Harry Winston diamonds, it was the latter. Why anyone wouldn’t love this look, we’re not sure, but does it matter? She took home the Best Actress award for her role in Shakespeare in Love and served one of the most remembered looks to date.

WHO: Celine Dion

WHAT: 1999 Academy Awards 

WEAR: Dior suit; fedora; diamond-studded Ray-Bans

The fashion critics in ‘99 were particularly harsh on Oscars red carpet looks, including Celine Dion’s white Dior satin pantsuit by John Galliano, which she wore styled backward. Little did they know, this would become one of her most iconic looks ever and one of the most-celebrated Academy Awards looks of all time. Guess it pays to think outside the box (or just to be Celine Dion).

WHO: Uma Thurman

WHAT: 1999 Academy Awards

WEAR: Chanel two-piecedress; bangle bicep cuffs 

Something must have been in the water at the 1999 Academy Awards because it served us some serious looks, particularly this two-piece Chanel outfit from Uma Thurman. Of course, it wasn’t her first time stealing the red carpet (she championed a silk lavender Prada dress in ‘94), but it’s an outfit that has left many in their feelings.

WHO: Cameron Diaz

WHAT: 2000 Academy Awards

WEAR: Versace gown 

While there are red carpet looks that are timeless, others, like a fine wine, take time to come into their own—that’s the case with Cameron Diaz’s ensemble for the 2000 Oscars. At the time, it could have been considered too risqué, but this see-through Versace gown, in many ways, was a precursor to the beloved naked dresses celebrities wear today.

WHO: Salma Hayek 

WHAT: 2000 Academy Awards

WEAR: Eric Gaskins gown

Salma Hayek has donned some of the chicest Oscars red carpet looks over the years, but none are quite as lovely as her ‘00s ceremony gown. The lavender, beaded Eric Gaskins gown with a deep V-neck may not be the most exuberant dress ever worn on the red carpet, but its subtle elegance is what makes it worthy of being considered one of the best Oscars looks of all time. 

WHO: Lucy Liu

WHAT: 2000 Academy Awards

WEAR: Versace dress 

As editors, we’re always delighted when we come across a resurging trend or a forgotten incredible red carpet look—that is the case with Lucy Liu’s ‘00s Oscars ensemble. The stunning red and black, one-shoulder Versace gown needs to be brought back into the cultural psyche because it’s just too good.

WHO: Jennifer Aniston and Brad Pitt 

WHAT: 2000 Academy Awards

WEAR: On Jennifer Aniston: Atelier Versace gown

The black dress is not a new concept to the red carpet, but no one can quite wear a deep V-neck black gown like Jennifer Aniston. Since her attendance at the ‘00s Academy Awards in Atelier Versace, she’s championed this cut time and again, but can you blame her? A dress this good deserves to be seen.

WHO: Halle Berry

WHAT: 2002 Academy Awards

WEAR: Elie Saab gown

There are numerous reasons why Halle Berry’s 2002 Oscars look can be considered one of the best of all time. Her half-sheer embroidered gown not only put Elie Saab on the map, but she also became the first Black woman to win Best Actress—talk about iconic.

WHO: Kate Hudson

WHAT: 2003 Academy Awards

WEAR: Atelier Versace gown

Encapsulating Hollywood glamour into a singular gown isn’t easy, but that’s precisely what Donatella Versace did with the stunning floor-length gold gown worn by Kate Hudson in ‘03. Every detail, from the hand-sewn embroidery to the 14k gold lining, on the effervescent Hudson makes this look worthy of its own award.

WHO: Charlize Theron 

WHAT: 2004 Academy Awards

WEAR: Gucci gown 

Charlize Theron’s performance in the film Monster isn’t the only thing worthy of an Oscar. Her red carpet look for the ‘04 ceremony is, too. Tom Ford designed the stunning strappy, bedazzled Gucci gown, and the pairing of Theron’s wavy hairdo and bleached eyebrows makes this a look we can’t forget.

WHO: Oprah Winfrey and Hilary Swank

WHAT: 2005 Academy Awards

WEAR: On Oprah Winfrey: Vera Wang gown; On Hilary Swank: Guy Laroche dress

What makes the Oscars red carpet unique is that the ensembles range from classic to cutting-edge at every ceremony. The two looks that distill the full scope of Oscar’s style are what Oprah Winfrey and Hilary Swank wore to the 2005 ceremony. Winfrey opted for a classic, fitted Vera Wang gown, while Swank donned a floor-length, open-back navy gown by Guy Laroche. The result? Two incredible women in two iconic looks that are worth thinking about. 

WHO: Reese Witherspoon

WHAT: 2006 Academy Awards

WEAR: vintage Christian Dior gown

Reese Witherspoon’s ‘06 Oscars gown may be considered traditional by most, but what makes this Dior dress immaculate is that this champagne-coloured beaded gown was found by her stylist in a vintage store in Paris. C'est magnifique.

WHO: Penelope Cruz

WHAT: 2007 Academy Awards

WEAR: Atelier Versace gown

I have yet to see an Atelier Versace red carpet look I did not love—Penelope Cruz’s ‘07 Oscar Awards ensemble is high up there for me. What’s fantastic about this look is that the pale-pink strapless gown has this stunning ruched bodice and full feather skirt, making it a dreamy, princess-like look that could only be embodied by Cruz herself.

WHO: Angelina Jolie 

WHAT: 2009 Academy Awards

WEAR: Elie Saab gown; emerald earrings 

My love for Angelina Jolie was cemented by her 2009 Oscars red carpet look. While some critics may consider the 2012 black high-slit Atelier Versace gown her best look of all time, I’ll go to bat for this look. Yes, the Elie Saab gown stole my heart, but Jolie’s stunning emerald earrings are what sealed the deal—the dramatic colour contrast, the size, and her damn cheekbones just make this look too divine for humanity.

WHO: Zoe Saldana 

WHAT: 2010 Academy Awards

WEAR: Givenchy Couture gown

Zoe Saldana’s 2010 Oscars red carpet look is lauded as one of the best looks of all time (for a good reason). While the star was nominated for the film Avatar that year, it’s her dress that was the genuinely out-of-this-world thing—the sequins and ombré tulle make this Givenchy Couture gown designed by Riccardo Tisci a celestial piece of Oscars history.

WHO: Rooney Mara

WHAT: 2012 Academy Awards

WEAR: Givenchy Couture

While Rooney Mara’s red carpet style may appear to be simple from far away, the intricate details, textures, and fit say otherwise. Take, for example, her 2012 Oscars red carpet look. To the objective on-looker, she’s wearing a simple white gown, but for the fashion crowd, we know that this Givenchy couture was custom-made by Riccardo Tisci with pearl-coloured lace.

WHO: Meryl Streep

WHAT: 2012 Academy Awards

WEAR: Lanvin gown and belt; Salvatore Ferragamo shoes

Meryl Streep stirred up the whole pot at the 2012 Academy Awards—and not just because she won Best Actress for her performance as Margaret Thatcher in The Iron Lady. Her choice of Lanvin garnered considerable discussion among the industry not just because people were unsure about the full-gold look but also because Streep selected Lanvin over Chanel for the ceremony. No matter what the tea is, this look is one we’ll be talking about for years to come.

WHO: Jennifer Lawerence and Anne Hathaway

WHAT: 2013 Academy Awards

WEAR: On Jennifer Lawerence: Dior Haute Couture gown; On Anne Hathaway: Prada gown

If you were to take a time machine back to the 2013 Oscars, you’d know that the buzz was all about Jennifer Lawerence and Anne Hathaway. Lawrence’s fall up the stairs to her acceptance speech and Hathaway’s "controversial” dress were the talk of the town. But the attention should have been focused on how they both handled the night with such grace (which is easy to do when you’re wearing Dior or Prada) and took away Oscars, too.

WHO: Lupita Nyong'o 

WHAT: 2014 Academy Awards

WEAR: Prada gown; Fred Leighton jewels and headband

Genuinely speaking, there is not a more iconic Oscars red carpet moment in recent history than Lupita Nyong’o’s 2014 ensemble. What made this look historic (other than her win of Best Supporting Actress that year) was this crystal-pleated, powder-blue, deep V-neck Prada gown. We could stare at this look forever.

WHO: Jennifer Lopez 

WHAT: 2015 Vanity Fair Oscar Party

WEAR: Zuhair Murad Couture dress; white fur. 

It’s no secret that Jennifer Lopez has her fair share of iconic looks; however, none quite hold the same place in my heart as her 2015 Oscars After-Party outfit. Yes, her Ellie Saab gown for the ceremony was stunning, but nothing quite distills the "J.Lo aesthetic” like this full-length sequin Zuhair Murad Couture dress and white fur stole. My only question is, does love not cost a thing? Because this gown sure looks like a million bucks.

WHO: Emma Stone

WHAT: 2015 Academy Awards

WEAR: Elie Saab gown

Let it be stated for the internet records that Emma Stone is secretly that girl who always brings her A game to the red carpet. Case in point: the green floor-length, high-slit, and sequinned Elie Saab gown she wore to the 2015 Academy Awards. This isn’t a bad look; it’s a super-bad look if you catch my drift.

WHO: Beyoncé and Solange Knowles

WHAT: 2015 Vanity Fair Oscars Party

WEAR: On Beyoncé: Stella McCartney white gown; J. Mendel fur; Lorraine Schwartz diamond and emerald earrings On Solange: Naeem Khan gown

If I could frame this photo of Beyoncé and Solange Knowles dancing at the 2015 Vanity Fair Oscars Party, I would. Does that make me an obsessive member of the Bey-hive? Sure. But the Knowles sisters never fail to serve a look—these matching white gowns are proof.

WHO: Jane Fonda

WHAT: 2015 Vanity Fair Oscars Party

WEAR: Zuhair Murad Haute Couture jumpsuit 

Whenever I see another red carpet look from the one-and-only Jane Fonda, I always pray that I can look as fabulous as her when I grow up. Of course, it doesn’t hurt to be able to wear a full-sequin Zuhair Murad Haute Couture jumpsuit, but then again, it’s Jane Fonda, and no one else can serve a red carpet look like her.

WHO: Kerry Washington

WHAT: 2016 Academy Awards

WEAR: Atelier Versace gown; Schutz shoes

Whether you’re a Scandal fan or just a Kerry Washington stan, the power of the ensemble she wore to the 2016 Oscars can not be understated. She slayed that carpet like a gladiator in head-to-toe (the ponytail, the Atelier Versace gown with a leather bodice and a high-slit, and the see-through Schutz heels) perfection.

WHO: Zendaya 

WHAT: 2018 Academy Awards

WEAR: Giambattista Valli Couture dress; Brian Atwood shoes; Bvlgari jewelry

There’s not a day that goes by that I don’t think about the incredible celebrity and stylist pairing that is Zendaya and Law Roach. The style companions have served us some of the most iconic red carpet looks to date, including this stunning floor-length, off-the-shoulder, chocolate-brown Giambattista Valli number. Zendaya, why do you do this to me?

WHO: Saoirse Ronan

WHAT: 2018 Academy Awards 

WEAR: Calvin Klein dress; Christian Louboutin shoes; Cartier jewelry

Compared to the over-the-top numbers the Oscars red carpet has seen in the past, Saoirse Ronan’s strapless pink Calvin Klein dress isn’t overly exuberant. But the oversize bow in the back makes this a lesson in understated elegance. This look could have been worn to the Oscars in the ‘50s or could easily make a statement well into the future. That’s what makes it iconic.

WHO:  SZA 

WHAT: 2019 Academy Awards

WEAR: custom Vivienne Westwood dress; Jennifer Behr hairpins; Bvlgari jewelry; Stuart Weitzman Nudist Disco shoes 

The great thing about the Oscars is that sometimes our favourite musicians will be nominated for film scores and show up wearing some of the best looks of the night—that was the case with SZA’s 2019 Oscars look. The stunning custom Vivienne Westwood dress with a corset bodice and a frayed hem had her looking like a supermodel.

WHO: Billy Porter

WHAT: 2019 Vanity Fair Oscars Party

WEAR: Christian Siriano tuxedo dress 

The Oscars red carpet hasn’t always been known to host the most stand-out looks from nominated actors and attendees, but every once in a while, we’re blessed with a few men who aren’t afraid to go bold. It doesn’t get bolder than actor and style icon Billy Porter—who else could pull off a Christian Siriano tuxedo dress? This is an Oscars red carpet look we’ll be talking about for years to come.

WHO: Gemma Chan

WHAT: 2019 Academy Awards

WEAR: Valentino Haute Couture dress; Bvlgari jewellery; Jimmy Choo shoes 

No one has ever entirely made a case for hot pink on the Oscars red carpet like Gemma Chan. Her voluminous Valentino Haute Couture gown is something I stare at when I feel I need a reminder that there are, indeed, beautiful things in the world.

WHO: Regina King 

WHAT: 2019 Academy Awards

WEAR: Oscar de la Renta dress; Chopard jewellery; Christian Louboutin shoes 

The 2019 Academy Awards was a huge night for Regina King, as she not only won Best Supporting Actress for the film If Beale Street Could Talk, but she also donned one of her best red carpet looks to date. Of course, King fans are well aware that she’s often one of the most stylish characters on-screen, but the stunning white Oscar de la Renta gown paired with matching Christian Louboutin shoes proved she’s a style icon IRL, too.

WHO: Lady Gaga

WHAT: 2019 Academy Awards

WEAR: Alexander McQueen dress; Tiffany & Co. jewellery

If you weren’t already a self-proclaimed Little Monster (like myself), the 2019 Oscars could have felt as if a star was born that evening. Of course, real Lady Gaga fans know she’s served iconic looks for years; her Oscar win (for best original song), the Alexander McQueen dress, and the yellow Tiffany & Co. necklace had her shinin’ like never before.

WHO: Janelle Monáe

WHAT: 2020 Academy Awards

WEAR: Ralph Lauren custom evening dress; Forevermark jewellery

I’ve said it before, and I’ll repeat it: Janelle Monáe does not play when it comes to her style. No gown better encompasses that ethos than the crystal-lacquered silk lamé, tulle mesh Ralph Lauren gown—featuring a draped hood and an open back—she wore to the 2020 Oscars. It took over 600 hours of handwork to embroider 168,000 Swarovski crystals on the dress, making it a masterpiece we won’t forget.

WHO: Timothée Chalamet and Margot Robbie

WHAT: 2020 Academy Awards

WEAR: On Timothée Chalamet: Prada jacket and trousers; Cartier Tradition brooch

If you know, you know that Timothée Chalamet is never one to shy away from serving a look. (He’ll wear men’s jewellery with ease.) Of course, that fearlessness is sometimes met with mass critique, most recently including strong feelings around his 2020 Oscars outfit. Instead of sticking to a tuxedo, he opted for an anti-suit: a Prada Re-Nylon gabardine jacket with satin racing stripes and matching Prada Re-Nylon trousers over a white poplin shirt. He finished the look with a Cartier Tradition brooch with 18k white gold, platinum, rubies, and diamonds. While the critics may not have been here for it, I have a feeling this look will go down in history as ushering in a new way for men to approach their Oscars red carpet looks.

WHO: Sandra Oh

WHAT: 2020 Vanity Fair Oscars Party

WEAR: Cong Tri dress; Messika jewellery; Stuart Weitzman shoes

One person can bring life or death by serving a look, and that’s no other than Grey’s Anatomy and Killing Eve star Sandra Oh. Her 2020 Vanity Fair Oscars Party look (a grey, floor-length, sequinned, feather-embellished, deep V-neck Cong Tri dress) had me in shambles.

WHO: Janet Mock

WHAT: 2020 Vanity Fair Oscars Party

WEAR: Oscar de la Renta dress

By now, you know that a list of the best Oscars looks of all time is subjective and ever-changing in the face of trends. Occasionally, there are hidden gems—like this Oscar de la Renta look Janet Mock wore to the Vanity Fair Oscars Party—that go unnoticed. But with time, reflection, and a whole lot of sequins, we’re able to see that the best Oscars looks of all time strike the perfect balance between being timeless and being of that time period. How to know if something can be considered stylish is in the eye of the beholder, I guess, but for now, I’ll keep staring at these looks.

Next Up: Every Incredible Look From the BAFTAs 2022 Red Carpet

This story originally appeared on Who What Wear US. 

After over a year and a half of canceled events and socially distant award shows, red carpets are back and bigger than ever with the arrival of the 2021 Met Gala. While there are plenty of celebrity moments I’ve been anticipating, Timothée Chalamet—tonight, a Met Gala co-chair—is one person I was most excited to see on the red carpet. He’s already been having some iconic fashion moments alongside Zendaya to promote the upcoming movie Dune, but his solo Met Gala look certainly didn’t disappoint.

Wearing a cropped Haider Ackermann jacket with a Cartier pin and brooch, Chalamet looks like he’s adhering to a white-tie dress code from the waist up. That is until you spot his slouchy white sweatpants and Converse sneakers. I thought I was over waist-up dressing and never imagined liking it on the red carpet, but Timmy has simply done it again and proven he is one of the most directional dressers on any red carpet.

On Timothée Chalamet: Haider Ackermann jacket; Rick Owens pants; Cartier pin and brooch; Converse sneakers

Shop Converse sneakers:

Next, these are the best red carpet looks from the 2021 Met Gala.

After over a year and a half of canceled events and socially distant award shows, red carpets are back and bigger than ever with the arrival of the 2021 Met Gala. While there are plenty of celebrity moments I’ve been anticipating, Timothée Chalamet—tonight, a Met Gala co-chair—is one person I was most excited to see on the red carpet. He’s already been having some iconic fashion moments alongside Zendaya to promote the upcoming movie Dune, but his solo Met Gala look certainly didn’t disappoint.

Wearing a cropped Haider Ackermann jacket with a Cartier pin and brooch, Chalamet looks like he’s adhering to a white-tie dress code from the waist up. That is until you spot his slouchy white sweatpants and Converse sneakers. I thought I was over waist-up dressing and never imagined liking it on the red carpet, but Timmy has simply done it again and proven he is one of the most directional dressers on any red carpet.

On Timothée Chalamet: Haider Ackermann jacket; Rick Owens pants; Cartier pin and brooch; Converse sneakers

Shop Converse sneakers:

Next, these are the best red carpet looks from the 2021 Met Gala.

In a time of mass uncertainty, it can seem trite to look forward to award season. But after a year of quarantining at home, film and television have become a shared source of joy amid the perils of the pandemic. Sure, many of us have spent the last several months in nothing fancier than sweatpants, but how we dress has always been indicative of our collective psyche, and no other event quite represents the current state than a Hollywood red carpet. Since 1929, the Academy Awards has maintained firm footing in the zeitgeist not only by being a point of contention and conversation but also for history-making moments, including some of the best red carpet looks of all time. While some years are more memorable than others, we prefer to focus on the standout moments that made us smile. Sequins, satin, and sleeveless dresses may be timeless, but the best Oscars looks of all time aren’t always the safest bet—they’re daring, bold, and sometimes deemed "the worst” at first, but that’s what makes them iconic. Ahead, you’ll find the 49 Oscars looks that surprise and delight and that were truly indicative of the times.

WHO: Audrey Hepburn and Jean Hersholt

WHAT: 1954 Academy Awards

WEAR: On Audrey Hepburn: Givenchy gown 

Oscars night 1954 was a major moment for Audrey Hepburn—not only did she win the Best Actress award for her breakout role in Roman Holiday, but it’s also worth noting that her custom-made Givenchy gown ushered in a new era in fashion. Hailed as one of the most classic dresses of the 20th century, this dress was indicative of Hepburn’s role as muse to French designer Hubert de Givenchy, and their relationship went on to change the way celebrities and designers worked together.

WHO: Grace Kelly and Edmond O'Brien

WHAT: 1955 Academy Awards

WEAR: On Grace Kelly: Edith Head gown and coat

It doesn’t get more glamorous than the future princess of Monaco, award-winning actress Grace Kelly. While she served quite a few iconic looks on- and off-screen, her custom-made Edith Head gown was her most iconic red carpet outfit for several reasons: That night, she took home the award for Best Actress (in the film The Country Girl), and it was one of the most expensive dresses worn to the ceremony, crafted from $4000 worth of French satin.

WHO: Elizabeth Taylor

WHAT: 1957 Academy Awards

WEAR: William Ruser tiara and earrings

Yes, gowns are an essential part of making the Oscars a true Hollywood affair, but let’s be honest: The jewelry really makes the night sparkle. No one quite knew the power of jewels like actress Elizabeth Taylor. After all, who else could pull off wearing a full-diamond tiara to the Academy Awards?

WHO: Barbra Streisand

WHAT: 1969 Academy Awards

WEAR: Arnold Scaasi pantsuit

Long before naked dresses and sheer jumpsuits were a thing, Barbra Streisand turned heads with her transparent pantsuit at the 1969 Academy Awards. Of course, the subtly sheer number was enhanced by the spotlights, but Streisand's star power—including taking home her first statue that night—was anything but accidental. 

WHO: Cher and Sonny Bono 

WHAT: 1973 Academy Awards 

WEAR: On Cher: Bob Mackie two-piece gown

Any Cher fan knows that she’s spent the duration of her career serving up iconic looks (she pioneered the naked-dress trend), but none are seared into our brains quite like her 1973 Oscars look. This stunning sequinned two-piece Bob Mackie gown is the stuff of psychedelic ‘70s dreams—not to mention, she looks fantastic. Cher, please drop the core workout routine.

WHO: Farrah Fawcett and Marcello Mastroianni 

WHAT: 1978 Academy Awards 

WEAR: On Farrah Fawcett: Stephen Burrows gown 

Farrah Fawcett’s slinky, gold Stephen Burrows gown rivals an Oscar statue itself.

WHO:  Diana Ross and Ernest Thompson 

WHAT: 1982 Academy Awards

WEAR: On Diana Ross: red sequin gown; white fur stole

If you’re coming out to the Oscars, you want to go all the way out. In the ‘80s, no one quite brought the glamour like singer and actress Diana Ross. This head-to-toe red sequinned gown is everything.

WHO: Whoopi Goldberg

WHAT: 1991 Academy Awards 

WEAR: black sequin column dress; pearl necklace and earrings

There are very few artists in the world who have won an EGOT—Whoppi Goldberg is one of them. Goldberg is the first-ever African American to be nominated for Best Actress and Best Supporting Actress (which she won in ‘91 for her performance in Ghost). Her look for the 1991 Academy Awards encompassed the type of popular sequinned column dresses that were everywhere during the late ‘80s and early ‘90s, making it historic in and of itself.

WHO: Madonna and Michael Jackson

WHAT: 1991 Academy Awards 

WEAR: On Madonna: Bob Mackie gown; Harry Winston diamond necklace and earrings 

Sooner or later, when it comes to rounding up a list of iconic red carpet looks, you have to include Madonna. Her ‘91 Oscars outfit was one for the history books, as she channeled Marilyn Monroe with a sequinned sweetheart-neckline Bob Mackie gown and $20 million worth of Harry Winston jewelry. Material girls, this is your look.

WHO: Sarah Jessica Parker and Matthew Broderick 

WHAT: 1993 Academy Awards 

WEAR: On Sarah Jessica Parker: brown sequin gown; blue-lens sunglasses 

Don’t get it twisted. Long before serving iconic on-screen looks as Carrie Bradshaw in Sex and the City, Sarah Jessica Parker was giving us head-to-toe ‘fits. Case in point: the simple yet very ‘90s brown sequin gown and blue-lens sunglasses she wore to the Academy Awards in 1993. 

WHO: Vanessa L. Williams 

WHAT: 1995 Academy Awards 

WEAR: sequin and mesh gown; pashmina; clutch bag

Remember the chocolate-brown, sequin, and mesh number Vanessa L. Williams wore in ‘95? The gown—with its multiple fabrics, color, and cut—was far ahead of its time and includes almost every ‘90s trend we hold dear today.

WHO: Naomi Campbell

WHAT: 1996 Academy Awards

WEAR: yellow gown; diamond choker

Honestly, is it even a roundup of the best red carpet looks of all time without Naomi Campbell? What’s great about her 1996 Oscars look is the sheer understated elegance of it—the yellow floor-length gown with the halter cut paired with a diamond choker necklace is just too good for words.

WHO: Jada Pinkett Smith and Will Smith 

WHAT: 1997 Academy Awards 

WEAR: On Jada Pinkett Smith: two-piece Versace dress

Although this coordinated red carpet look from Jada Pinkett Smith and husband Will Smith may have been questionable at the time, it’s now a secret iconic gem. Not only was her vibrant green two-piece gown Versace, but the midriff-bearing look was also very indicative of the trends to come that would influence the future of all "risqué” red carpet looks.

WHO: Nicole Kidman and Tom Cruise 

WHAT: 1997 Academy Awards 

WEAR: On Nicole Kidman: Christian Dior Couture gown

When we think of the Oscars today, we think of couture, but that wasn’t the standard in 1997. Nicole Kidman’s stunning yellow Christian Dior Couture gown put newly appointed John Galliano on the map and couture on the carpet, elevating both the fashion industry’s profile in Hollywood and the Oscars red carpet for years to come.

WHO: Gwyneth Paltrow

WHAT: 1999 Academy Awards 

WEAR: Ralph Lauren ball gown; Harry Winston diamond necklace and earrings 

At the time of their debuts on the carpet, many of the most iconic Oscar looks were met with either fanfare or outright disgust. For Gwyneth Paltrow’s 1999 bubblegum-pink Ralph Lauren gown with $160,000 worth of Harry Winston diamonds, it was the latter. Why anyone wouldn’t love this look, we’re not sure, but does it matter? She took home the Best Actress award for her role in Shakespeare in Love and served one of the most remembered looks to date.

WHO: Celine Dion

WHAT: 1999 Academy Awards 

WEAR: Dior suit; fedora; diamond-studded Ray-Bans

The fashion critics in ‘99 were particularly harsh on Oscars red carpet looks, including Celine Dion’s white Dior satin pantsuit by John Galliano, which she wore styled backward. Little did they know, this would become one of her most iconic looks ever and one of the most celebrated Academy Awards looks of all time. Guess it pays to think outside the box (or just to be Celine Dion).

WHO: Uma Thurman

WHAT: 1999 Academy Awards

WEAR: two-piece Chanel dress; bangle bicep cuffs 

Something must have been in the water at the 1999 Academy Awards because it served us some serious looks, particularly this two-piece Chanel outfit from Uma Thurman. Of course, it wasn’t her first time stealing the red carpet (she championed a silk lavender Prada dress in ‘94), but it’s an outfit that has left many in their feelings.

WHO: Cameron Diaz

WHAT: 2000 Academy Awards

WEAR: Versace gown 

While there are red carpet looks that are timeless, others, like a fine wine, take time to come into their own—that’s the case with Cameron Diaz’s ensemble for the 2000 Oscars. At the time, it could have been considered too risqué, but this see-through Versace gown, in many ways, was a precursor to the beloved naked dresses celebrities wear today.

WHO: Salma Hayek 

WHAT: 2000 Academy Awards

WEAR: Eric Gaskins gown

Salma Hayek has donned some of the chicest Oscars red carpet looks over the years, but none are quite as lovely as her ‘00s ceremony gown. The lavender, beaded Eric Gaskins gown with a deep V-neck may not be the most exuberant dress ever worn on the red carpet, but its subtle elegance is what makes it worthy of being considered one of the best Oscars looks of all time. 

WHO: Lucy Liu

WHAT: 2000 Academy Awards

WEAR: Versace dress 

As editors, we’re always delighted when we come across a resurging trend or a forgotten incredible red carpet look—that is the case with Lucy Liu’s ‘00s Oscars ensemble. The stunning red and black, one-shoulder Versace gown needs to be brought back into the cultural psyche because it’s just too good.

WHO: Jennifer Aniston and Brad Pitt 

WHAT: 2000 Academy Awards

WEAR: On Jennifer Aniston: Atelier Versace gown

The black dress is not a new concept to the red carpet, but no one can quite wear a deep V-neck black gown like Jennifer Aniston. Since her attendance at the ‘00s Academy Awards in Atelier Versace, she’s championed this cut time and again, but can you blame her? A dress this good deserves to be seen.

WHO: Halle Berry

WHAT: 2002 Academy Awards

WEAR: Elie Saab gown

There are numerous reasons why Halle Berry’s 2002 Oscars look can be considered one of the best of all time. Her half-sheer embroidered gown not only put Elie Saab on the map, but she also became the first Black woman to win Best Actress—talk about iconic.

WHO: Kate Hudson

WHAT: 2003 Academy Awards

WEAR: Atelier Versace gown

Encapsulating Hollywood glamour into a singular gown isn’t easy, but that’s precisely what Donatella Versace did with the stunning floor-length gold gown worn by Kate Hudson in ‘03. Every detail, from the hand-sewn embroidery to the 14k gold lining, on the effervescent Hudson makes this look worthy of its own award.

WHO: Charlize Theron 

WHAT: 2004 Academy Awards

WEAR: Gucci gown 

Charlize Theron’s performance in the film Monster isn’t the only thing worthy of an Oscar. Her red carpet look for the ‘04 ceremony is, too. Tom Ford designed the stunning strappy, bedazzled Gucci gown, and the pairing of Theron’s wavy hairdo and bleached eyebrows makes this a look we can’t forget.

WHO: Oprah Winfrey and Hilary Swank

WHAT: 2005 Academy Awards

WEAR: On Oprah Winfrey: Vera Wang gown; On Hilary Swank: Guy Laroche dress

What makes the Oscars red carpet unique is that the ensembles range from classic to cutting-edge at every ceremony. The two looks that distill the full scope of Oscar’s style are what Oprah Winfrey and Hilary Swank wore to the 2005 ceremony. Winfrey opted for a classic, fitted Vera Wang gown, while Swank donned a floor-length, open-back navy gown by Guy Laroche. The result? Two incredible women in two iconic looks that are worth thinking about. 

WHO: Reese Witherspoon

WHAT: 2006 Academy Awards

WEAR: vintage Christian Dior gown

Reese Witherspoon’s ‘06 Oscars gown may be considered traditional by most, but what makes this Dior dress immaculate is that this champagne-colored beaded gown was found by her stylist in a vintage store in Paris. C'est magnifique.

WHO: Penelope Cruz

WHAT: 2007 Academy Awards

WEAR: Atelier Versace gown

I have yet to see an Atelier Versace red carpet look I did not love—Penelope Cruz’s ‘07 Oscar Awards ensemble is high up there for me. What’s fantastic about this look is that the pale-pink strapless gown has this stunning ruched bodice and full feather skirt, making it a dreamy, princess-like look that could only be embodied by Cruz herself.

WHO: Angelina Jolie 

WHAT: 2009 Academy Awards

WEAR: Elie Saab gown; emerald earrings 

My love for Angelina Jolie was cemented by her 2009 Oscars red carpet look. While some critics may consider the 2012 black high-slit Atelier Versace gown her best look of all time, I’ll go to bat for this look. Yes, the Elie Saab gown stole my heart, but Jolie’s stunning emerald earrings are what sealed the deal—the dramatic color contrast, the size, and her damn cheekbones just make this look too divine for humanity.

WHO: Zoe Saldana 

WHAT: 2010 Academy Awards

WEAR: Givenchy Couture gown

Former cover star Zoe Saldana’s 2010 Oscars red carpet look is lauded as one of the best looks of all time (for a good reason). While the star was nominated for the film Avatar that year, it’s her dress that was the genuinely out-of-this-world thing—the sequins and ombré tulle make this Givenchy Couture gown designed by Riccardo Tisci a celestial piece of Oscars history.

WHO: Rooney Mara

WHAT: 2012 Academy Awards

WEAR: Givenchy Couture

While Rooney Mara’s red carpet style may appear to be simple from far away, the intricate details, textures, and fit say otherwise. Take, for example, her 2012 Oscars red carpet look. To the objective on-looker, she’s wearing a simple white gown, but for the fashion crowd, we know that this Givenchy couture was custom-made by Riccardo Tisci with pearl-colored lace.

WHO: Meryl Streep

WHAT: 2012 Academy Awards

WEAR: Lanvin gown and belt; Salvatore Ferragamo shoes

Meryl Streep stirred up the whole pot at the 2012 Academy Awards—not just because she won Best Actress for her performance as Margaret Thatcher in The Iron Lady. Her choice of Lanvin garnered considerable discussion among the industry not just because people were unsure about the full-gold look but also because Streep selected Lanvin over Chanel for the ceremony. No matter what the tea is, this look is one we’ll be talking about for years to come.

WHO: Jennifer Lawerence and Anne Hathaway

WHAT: 2013 Academy Awards

WEAR: On Jennifer Lawerence: Dior Haute Couture gown; On Anne Hathaway: Prada gown

If you were to take a time machine back to the 2013 Oscars, you’d know that the buzz was all about Jennifer Lawerence and Anne Hathaway. Lawrence’s fall up the stairs to her acceptance speech and Hathaway’s "controversial” dress were the talk of the town. But the attention should have been focused on how they both handled the night with such grace (which is easy to do when you’re wearing Dior or Prada) and took away Oscars, too.

WHO: Lupita Nyong'o 

WHAT: 2014 Academy Awards

WEAR: Prada gown; Fred Leighton jewels and headband

Genuinely speaking, there is not a more iconic Oscars red carpet moment in recent history than Lupita Nyong’o’s 2014 ensemble. What made this look historic (other than her win of Best Supporting Actress that year) was this crystal-pleated, powder-blue, deep V-neck Prada gown. We could stare at this look forever.

WHO: Jennifer Lopez 

WHAT: 2015 Vanity Fair Oscar Party

WEAR: Zuhair Murad Couture dress; white fur. 

It’s no secret that Jennifer Lopez has her fair share of iconic looks; however, none quite hold the same place in my heart as her 2015 Oscars After-Party outfit. Yes, her Ellie Saab gown for the ceremony was stunning, but nothing quite distills the "J.LO aesthetic” like this full-length sequin Zuhair Murad Couture dress and white fur stole. My only question is, does love not cost a thing? Because this gown sure looks like a million bucks.

WHO: Emma Stone

WHAT: 2015 Academy Awards

WEAR: Elie Saab gown

Let it be stated for the internet records that Emma Stone is secretly that girl who always brings her A game to the red carpet. Case in point: the green floor-length, high-slit, and sequinned Elie Saab gown she wore to the 2015 Academy Awards. This isn’t a bad look; it’s a super-bad look if you catch my drift.

WHO: Jane Fonda

WHAT: 2015 Vanity Fair Oscars Party

WEAR: Zuhair Murad Haute Couture jumpsuit 

Whenever I see another red carpet look from the one-and-only Jane Fonda, I always pray that I can look as fabulous as her when I grow up. Of course, it doesn’t hurt to be able to wear a full-sequin Zuhair Murad Haute Couture jumpsuit, but then again, it’s Jane Fonda, and no one else can serve a red carpet look like her.

WHO: Kerry Washington

WHAT: 2016 Academy Awards

WEAR: Atelier Versace gown; Schutz shoes

Whether you’re a Scandal fan or just a Kerry Washington stan, the power of the ensemble she wore to the 2016 Oscars can not be understated. She slayed that carpet like a gladiator in head-to-toe (the ponytail, the Atelier Versace gown with a leather bodice and a high-slit, and the see-through Schutz heels) perfection.

WHO: Zendaya 

WHAT: 2018 Academy Awards

WEAR: Giambattista Valli Couture dress; Brian Atwood shoes; Bvlgari jewelry

There’s not a day that goes by that I don’t think about the incredible celebrity and stylist pairing that is Zendaya and Law Roach. The style companions have served us some of the most iconic red carpet looks to date, including this stunning floor-length, off-the-shoulder, chocolate-brown Giambattista Valli number. Zendaya, why do you do this to me?

WHO: Saoirse Ronan

WHAT: 2018 Academy Awards 

WEAR: Calvin Klein dress; Christian Louboutin shoes; Cartier jewelry

Compared to the over-the-top numbers the Oscars red carpet has seen in the past, Saoirse Ronan’s strapless pink Calvin Klein dress isn’t overly exuberant. But the oversize bow in the back makes this a lesson in understated elegance. This look could have been worn to the Oscars in the ‘50s or could easily make a statement well into the future. That’s what makes it iconic.

WHO:  SZA 

WHAT: 2019 Academy Awards

WEAR: custom Vivienne Westwood dress; Jennifer Behr hairpins; Bvlgari jewelry; Stuart Weitzman Nudist Disco shoes 

The great thing about the Oscars is that sometimes our favorite musicians will be nominated for film scores and show up wearing some of the best looks of the night—that was the case with SZA’s 2019 Oscars look. The stunning custom Vivienne Westwood dress with a corset bodice and a frayed hem had her looking like a supermodel.

WHO: Billy Porter

WHAT: 2019 Vanity Fair Oscars Party

WEAR: Christian Siriano tuxedo dress 

The Oscars red carpet hasn’t always been known to host the boldest looks from nominated actors and attendees, but every once in a while, we’re blessed with a few men who aren’t afraid to go bold. It doesn’t get bolder than actor and style icon Billy Porter—who else could pull off a Christian Siriano tuxedo dress? Like it or not, this is an Oscars red carpet look we’ll be talking about for years to come.

WHO: Gemma Chan

WHAT: 2019 Academy Awards

WEAR: Valentino Haute Couture dress; Bvlgari jewelry; Jimmy Choo shoes 

No one has ever entirely made a case for hot pink on the Oscars red carpet like Gemma Chan. Her voluminous Valentino Haute Couture gown is something I stare at when I feel I need a reminder that there are, indeed, beautiful things in the world.

WHO: Regina King 

WHAT: 2019 Academy Awards

WEAR: Oscar de la Renta dress; Chopard jewelry; Christian Louboutin shoes 

The 2019 Academy Awards was a huge night for Regina King, as she not only won Best Supporting Actress for the film If Beale Street Could Talk, but she also donned one of her best red carpet looks to date. Of course, King fans are well aware that she’s often one of the most stylish characters on-screen, but the stunning white Oscar de la Renta gown paired with matching Christian Louboutin shoes proved she’s a style icon IRL, too.

WHO: Lady Gaga

WHAT: 2019 Academy Awards

WEAR: Alexander McQueen dress; Tiffany & Co. jewelry

If you weren’t already a self-proclaimed Little Monster (like myself), the 2019 Oscars could have felt as if a star was born that evening. Of course, real Lady Gaga fans know she’s served iconic looks for years; her Oscar win (for best original song), the Alexander McQueen dress, and the yellow Tiffany & Co. necklace had her shinin’ like never before.

WHO: Janelle Monáe

WHAT: 2020 Academy Awards

WEAR: Ralph Lauren custom evening dress; Forevermark jewelry

I’ve said it before, and I’ll repeat it: Janelle Monáe does not play when it comes to her style. No gown better encompasses that ethos than the crystal-lacquered silk lamé, tulle mesh Ralph Lauren gown—featuring a draped hood and an open back—she wore to the 2020 Oscars. It took over 600 hours of handwork to embroider 168,000 Swarovski crystals on the dress, making it a masterpiece we won’t forget.

WHO: Timothée Chalamet and Margot Robbie

WHAT: 2020 Academy Awards

WEAR: On Timothée Chalamet: Prada jacket and trousers; Cartier Tradition brooch

If you know, you know that Timothée Chalamet is never one to shy away from serving a look. (He’ll wear men’s jewelry with ease.) Of course, that fearlessness is sometimes met with mass critique, most recently including strong feelings around his 2020 Oscars outfit. Instead of sticking to a tuxedo, he opted for an anti-suit: a Prada Re-Nylon gabardine jacket with satin racing stripes and matching Prada Re-Nylon trousers over a white poplin shirt. He finished the look with a Cartier Tradition brooch with 18k white gold, platinum, rubies, and diamonds. While the critics may not have been here for it, I have a feeling this look will go down in history as ushering in a new way for men to approach their Oscars red carpet looks.

WHO: Sandra Oh

WHAT: 2020 Vanity Fair Oscars Party

WEAR: Cong Tri dress; Messika jewelry; Stuart Weitzman shoes

One person can bring life or death by serving a look, and that’s no other than Grey’s Anatomy and Killing Eve star Sandra Oh. Her 2020 Vanity Fair Oscars Party look (a gray, floor-length, sequinned, feather-embellished, deep V-neck Cong Tri dress) had me in shambles.

WHO: Janet Mock

WHAT: 2020 Vanity Fair Oscars Party

WEAR: Oscar de la Renta dress

By now, you know that a list of the best Oscars looks of all time is subjective and ever-changing in the face of trends. Occasionally, there are hidden gems—like this Oscar de la Renta look Janet Mock wore to the Vanity Fair Oscars Party—that go unnoticed. But with time, reflection, and a whole lot of sequins, we’re able to see that the best Oscars looks of all time strike the perfect balance between being timeless and being of that time period. How to know if something can be considered stylish is in the eye of the beholder, I guess, but for now, I’ll keep staring at these looks.

Next: These Are the Craziest Oscars Gowns Ever

While this story may have started out as an excuse to write about my lowkey obsession with Timothée Chalamet, I've actually become full-on inspired by his style risks at movie premieres and his luxe but cool looks he dons around NYC. My usual go-to for celebrity outfit inspiration is Bella Hadid, but I may be expanding to take cues from male stars like Chalemet because it's evident that he knows how to embrace the spectrum of style.

While many young male celebrities opt for the simplicities of a black tuxedo on the red carpet, Chalamet takes the extra mile with pops of bright hues. The star isn't pictured by paparazzi as often as others, but when he is, he's usually sporting top designers like Prada and Gucci, but fitting them effortlessly into his relaxed outfits that consist of joggers and sneakers. 

Below, I've rounded up all my favorite looks of the star that I can actually see myself recreating. And if there's anything to be said about 2020, it's that it gave a copious amount of Timmy content—from the Dune trailer to his GQ cover to his Saturday Night Live episode. Basically, it's Timothée Chalamet's world, and we're just living in it.

On Timothée: Haider Ackermann outfit

I'm not sure what I love more about this look: the monochromatic colors or the leather boots he tends to gravitate toward on the red carpet. Either way, I think I'm going to have to start braving bold colors soon.

On Timothée: Prada jacket; Adidas 3-Stripes Pants ($65); Celine sneakers 

While this seems like a typical athleisure ensemble, it isn't till you notice that the nylon jacket is Prada, and he paired trendy patterned socks with Celine sneakers. Talk about a subtle flex. 

He doesn't post on Instagram often, but when he does, he's sure to start a trend. This makes me want to upgrade my basic white tops with colorful baggy jeans or trousers.

On Timothée: Stussy sweater

Timothée Chalamet wore a puffer vest, so I wore a puffer vest. On a real fashion note, puffer vests are trending increasingly high this winter. This outfit is simple and is exactly what I want to wear when it's cold out. 

On Timothée: Gucci sweater, shirt, and loafers

When the best worlds collide. I know—technically, this Timothée acting as Harry Styles, but we have to admit, he pulls off that sweater and collar so well that I had to include it. 

Here he makes yet another case for a monochromatic look, but also for corduroy which, I've been seeing more of on the fashion scene lately. 

On Timothée: Saint Laurent jacket

For those days where you don't want to think too much about an outfit, pair a colored jacket over all-black basics.

Shop Timothée's Favorite Fashion Items

Every once in a while, there’s a moment where all my favorite interests intersect, and my love for film, music, pop culture, and fashion become one. Luckily, this culmination has come to a head in one specific trend that lives in my mind rent-free: Men in jewelry. Of course, men’s jewelry is by no means anything new. In more recent history, the ‘80s had a plethora of famous men such as Prince, Dennis Rodman, and Lenny Kravitz who weren’t afraid to layer on the jewels. These icons paved the way for the moments my colleagues and I tend to gush over: Hollywood’s best-dressed men showing up to the red carpet dripping in jewels. 

And while it may be easy to write off men’s jewelry as something only Harry Styles could pull off, it seems that the trend is everywhere. From popular shows like Hulu’s original series, Normal People creating buzz around Paul Mescal’s character’s signature chain, to Spring/Summer 2021’s most prominent jewelry trends, it’s been made crystal clear that the jewels aren’t just for the girls. Jewelry is universal—it is something that anyone can wear, as it’s unisex and can challenge gender norms. But if you’re not convinced just yet, keep scrolling as we’ve rounded up 21 famous men that make a serious case for men’s jewelry. Just a warning, though: Their drip may cause severe dehydration.

WHO: A$AP Rocky

WHAT: Loewe Paris Fashion Week SS20

WEAR: Choker and pearls

No one quite champions men’s jewelry quite like A$AP Rocky. As someone that’s always been a "fashion killa,” he jumped on the jewelry bandwagon long before anyone else. Rocky embraces all jewelry like it’s no problem on the red carpet or at a runway presentation.

Re-create this look:

WHO: Timotheé Chalamet

WHAT: Little Women Premiere in Paris, 2019

WEAR: Rings and a keychain

If you thought I forgot about the time Timotheé Chalamet showed up to the premiere of Little Women wearing a chain, rings and carrying a single Eiffel Tower keychain, then think again. Does a keychain technically count as jewelry? Not really, but seeing accessories of all kinds being worn as such is something that we can get behind thoroughly.

Re-create this look:

WHO: Bad Bunny

WHAT: Spotify Awards, 2020  

WEAR: Pearl necklaces, gold chains, and pendant necklaces

Latin pop sensation Bad Bunny is never afraid to serve a look or layer on the jewels. From wearing a full diamond face mask to layering on pearls and chains from some of our favorite demi-fine jewelry brands, Bad Bunny continuously challenges gender norms through his approach to personal style, one necklace at a time.

Re-create this look:

WHO: Machine Gun Kelly 

WHAT: 2020 MTV Video Music Awards

WEAR: Pearl necklace with silver hardware

If Avril Lavigne’s famous song, Sk8er Boi, had a physical manifestation, it would be in the form of a string of pearls on Machine Gun Kelly’s neck. There are many iconic MTV Video Music Awards looks, but the artist’s pink head-to-toe outfit with a single string of pearls shook the internet in a way that ensures its place in history books. Whoever said boys don’t wear pink or pearls never met MGK.

Re-create this look:

WHO: Aubrey Drake Graham

WHAT: Top Boy UK Premiere, 2019

WEAR: Diamond necklace. 

I’ve always been a serious Drake fan, but for me, it goes beyond his music. No other male artist has been able to elevate the cause of men’s jewelry quite like Champagne Papi. You can always find Drake dancing in some diamonds somewhere. And while he may be championing OVO’s first F/W 2020 women’s collection, one thing we can always thank Drake for his love for big rings.

Re-create this look:

WHO: Charles Melton

WHAT: Bad Boys for Life film premiere, 2020

WEAR: Single chain

We here at Who What Wear have always been fans of Charles Melton and his style. Can you blame us? Take his look above for an example; styling a classic cut suit with a single chain is too much to handle. All we know is that while his relationship status may be TBD, the star’s ability to make us thirsty for more men in jewelry is a given.

Re-create this look:

WHO: Yahya Abdul-Mateen II 

WHAT: 31st Annual Producers Guild Awards

WEAR: Brooch and chain

Confession: Ever since spotting actor Yahya Abdul-Mateen II in HBO’s Watchmen series, my friends and I have been somewhat obsessed with him. It’s not just the fact he unabashedly posts things on Instagram that would be considered a "trap,” or even that he recently won a Primetime Emmy Award for Outstanding Supporting Actor; it’s a fact he knows how to serve a look. I mean, what other man can wear a pink suit with a brooch and chain and still make a girl swoon? Yes, I’ve fallen, and no, I really can’t get over this.

Re-create this look:

WHO: Maluma 

WHAT: 2020 MTV Video Music Awards 

WEAR: Oversize chunky choker necklace

Despite the fact we’re in the middle of a pandemic, the men of Hollywood did not fail to bring the heat when it came to serving up some of the spiciest jewelry looks this year. One of those men was the Colombian singer Maluma. Pairing suits with on-trend jewelry pieces such as oversized statement chunky chokers burned down the notion of an otherwise boring suit.

Re-create this look:

WHO: Justin Bieber 

WHAT: SNL Rehearsals, 2020

WEAR: Beaded necklace

While we’ve spent copious amounts of time obsessing over Hailey Bieber’s style, it should be stated on the record that we shouldn’t ignore Justin Bieber himself. Not only does he know how to serve a street-style look (and even has his line of merchandise), but he’s a great example of how to style men’s jewelry for everyday use. Pairing kitschy beaded pieces with a jumper is only one example of the down-right yummy jewelry looks he’s able to cook up.

Re-create this look:

WHO: Lakeith Stanfield 

WHAT: ABC's Jimmy Kimmel Live

WEAR: Long pendant necklace

The first time I saw Lakeith Stanfield on screen, it was in FX’s breakout show Atlanta. Since that moment, I’ve remained intrigued. Not just because he always plays rather eccentric and dark characters (aside from starring alongside Issa Rae in the romantic film The Photograph), but also because his style is eclectic. He’s never afraid to layer on the rings or the pendant necklaces, and for that, I have the utmost respect.

Re-create this look:

WHO: Shawn Mendes 

WHAT: 62nd Annual Grammy Awards 

WEAR: Precious gemstone and diamond necklace

Another artist leading the way when it comes to wearing men’s jewelry on and off the red carpet? None other than Canadian singer-songwriter Shawn Mendes. Maybe it’s the music, or perhaps it’s the fact he wears gemstone and diamond necklaces with ease that causes us to be weak in the knees. How will we ever know?

Re-create this look:

WHO: Jaden Smith 

WHAT: 2020 MTV Video Music Awards

WEAR: Colorful pearls and layered on chain bracelets

Long before it was popular or socially "acceptable,” Jaden Smith used style to challenge gender norms around what’s considered apropos dressing for men. His ability to pull off everything from skirts to layered on pearls has made him a style icon in his own right.

Re-create this look:

WHO: Brad Pitt

WHAT: 76th Venice Film Festival 

WEAR: Layered long necklaces

If you thought that this list only included the newer faces to Hollywood, you guessed wrong. Jewelry isn’t just for the "younger” or female-identifying—it is universal, people. And no one quite makes a case for men’s jewelry better for it than veteran star Brad Pitt. If Pitt approves, then everyone else needs to get in line.

Re-create this look:

WHO: Michael B. Jordan 

WHAT: ABC's Jimmy Kimmel Live

WEAR: A pinky ring

It’s not a roundup of men who can make a girl drool without the one and only Michael B. Jordan. Aside from being named People’s sexiest man alive or starring in some of the most beloved films, Jordan knows how to rock some jewels (I’m not talking about wedding bands, either). He’s regularly spotted wearing a pinky ring, and that, my friends, is male chicness.

Re-create this look:

WHO: Jason Momoa 

WHAT: 77th Annual Golden Globe Awards 

WEAR: Brooch, oversize jade pendant necklace

Some men can wear the hell out of some gemstones. Jason Moma is one of them. If you’re worried that a men’s jewelry piece with stones such as jade or turquoise may feel too bohemian, then we highly recommend taking a cue from Momoa and pairing it with a suit for a look that may have earthy vibes but is downright heavenly.

Re-create this look:

WHO: Alexander Hodge

WHAT: Sundance Film Festival, 2020

WEAR: Small hoop earrings, silver cuff, turquoise bracelet

Insecure fans know that the breakout bae of the last season of the show was actor Alexander Hodge. And while his role as Andrew is worth watching, his style is something that deserves to be on your radar as well. He's never afraid to shy away from studs, a long chain, or layered bracelets. 

Re-create this look:

WHO: Lil Nas X

WHAT: Tom Ford A/W 20 Show

WEAR: Single hoop earring

Music genres aren’t the only thing that Lil Nas X has crossed since rising to fame—his approach to style knows no bounds. From serving up head-to-toe sequin looks at the 2019 MTV VMAs to never being afraid to shying away from wearing a single earring, Lil Nas X is the rapper proving both that men can sparkle just as much as women.

Re-create this look:

WHO: Jacob Elordi

WHAT: Napa Valley Film Festival, 2020

WEAR: Minimal silver pieces

While most people would say Jacob Elordi’s breakout performance in HBO’s Euphoria is what caught their attention, for me, it’s his ability to rock some jewelry. What’s noteworthy about his approach to styling jewelry is that he opts for minimal layering pieces that aren’t overtly attention-grabbing but are intriguing enough to give the newcomer a second glance.

Re-create this look:

WHO: Suga (Min Yoon-gi) of BTS 

WHAT: 2019 Billboard Music Awards 

WEAR: Small hoops

Please do not come after me, but I’m fully aware that there are other members of the wildly popular Korean band BTS that wear jewelry like pros. But I’m quite obsessed with the fact Suga always is wearing hoops. He’ll pair them with everything from cropped sweaters to bedazzled suits, really solidifying the point that jewelry looks just as good on the boys as the girls.

Re-create this look:

WHO: Harry Styles

WHAT: The BRIT Awards 2020 

WEAR: Single pearl 

You’ve made it to the end, and if your will is strong, then you’re not fully dehydrated from the full thirst-trap this story is meant to be. But don’t count your blessings yet because we still haven’t taken a moment to recognize our favorite British pop star, Harry Styles. Many celebrities have championed men’s jewelry, but none have quite been able to captivate the conversation around men in pearls, quite like Styles. After all, who else had a plethora of stars—including Timotheé Chalamet himself—make a nod to his iconic style on Saturday Niight Live? Whether you’re for or against men’s jewelry, it doesn’t matter because Harry Styles had made it here to stay.

Re-create this look:

WHO: Dev Patel 

WHAT: The Personal History of David Copperfield premiere, 2019

WEAR: Watch 

When all else fails and you’ve reached the end of a story about men’s jewelry and still aren’t sold, you turn to the one and only: Dev Patel. Embracing jewelry is a journey, and if you even can’t wrap your head around the idea of you (or your favorite man) stepping out in some pearls, then start simply with a good watch. I promise it’s something the most jewelry-adverse men can get behind.

Re-create this look:

Shop more jewelry that the men or women in your life will love:

Next: The 9 Spring 2021 Jewelry Trends You'll Actually Be Excited to Wear

Is it weird that I'm a 36-year-old woman and yet I want to dress like Timothée Chalamet? I'm going to go with no. He's a budding style icon that everyone can and should appreciate—team Who What Wear certainly does. Fresh off of his first-ever SNL hosting gig the night before (which produced more viral moments than I can even name), Chalamet headed out to do the usual Sunday morning activities (I assume) wearing an outfit that proves exactly why he's a budding style icon.

Not sure if you've noticed, but even when he's just wandering around NYC, Chalamet is always low-key decked out in designer pieces. In this case, it's a nylon Prada jacket (that I very much want) and Celine sneakers. But with his high-end gear was a pair of red Adidas joggers that go for well under $100—a lot more attainable than his $1.5k-ish jacket. Along with the zip-up polo top, patterned socks, and white sneakers, it's kind of the perfect casual outfit and it's kind of making me want to wear three-stripe Adidas joggers for the first time ever. If you're inspired too, keep scrolling to potentially buy a pair for yourself. (And I threw in a few nylon Prada jackets too, just in case.)

On Timothée Chalamet: Prada jacket; Adidas Adicolor Classics Track Pants ($65); Celine sneakers

Shop Adidas Track Pants

Next up, the jacket all the celebs are wearing (again).

Shop Prada Nylon Jackets

Imagine this: A golden boy in a sparkly hoodie steps onto a crimson carpet in London. Minutes later, millions of thumbs robotically refresh Instagram for just one more angle. Timothée Chalamet immediately trends worldwide. Again. That's a real story; my thumb was one of those worn out from scrolling the night he lit up London in the year's most spectacular sweatshirt. According to Lyst's Year in Fashion, the aforementioned hoodie, a standout Louis Vuitton piece, cemented the actor's place among Hollywood's best dressed men and even caused a 192% spike in searches for men's hoodies in general. Meanwhile, Timothée wore so much Haider Ackermann this year that he created the most organic interest in any designer for 2019—more than Meghan Markle.

The revered young actor, just a few steps into his ascent up the Hollywood ladder, is no stranger to such fervent regard, not after all the hullabaloo over his turn in Call Me By Your Name. (Well deserved, it must be said.) Still, Timothée has a lot of eyes on him, many of which are particularly attuned to his wardrobe choices—picks he chooses himself, having eschewed the traditional actor-and-stylist setup. That's not to say he doesn't have significant relationships with certain designers. It's clear he favors Haider Ackermann, Louis Vuitton, and Alexander McQueen. Those relationships are mutually beneficial, clearly, as every outfit he wears sets the internet alight but is also creatively inspiring—think a canvas of International Klein Blue, tie-dye overalls, checkerboard pants, and more.

With some big projects on the horizon, notably Little Women, which drops Christmas Day of this year, this wunderkind will no doubt give us more to discuss. For now, keep scrolling for all of Timothée Chalamet's best looks of 2019 and beyond.

WHAT: Australian premiere of The King at Ritz Cinema in Sydney, Australia

WEAR: Haider Ackermann outfit

WHAT: 24th Busan International Film Festival

WEAR: S.R. Studio. LA. CA. shirt, overalls, and boots

WHAT: 24th Busan International Film Festival 

WEAR: Haider Ackermann outfit

WHAT: New York premiere of The King at SVA Theater

WEAR: Givenchy suit and turtleneck

WHAT: The King premiere at the 63rd BFI London Film Festival 

WEAR: Louis Vuitton hoodie

WHAT: 76th Venice Film Festival 

WEAR: Haider Ackermann outfit

WHAT: 76th Venice Film Festival

WHERE: Haider Ackermann outfit

WHAT: EE British Academy Film Awards

WEAR: Haider Ackermann outfit

WHAT: Louis Vuitton Menswear F/W 19 show

WHAT: 25th Annual Screen Actors Guild Awards

WEAR: Celine jacket, shirt, and pants

WHAT: 24th annual Critics' Choice Awards

WEAR: Alexander McQueen suit

WHAT: 76th annual Golden Globe Awards

WEAR: Louis Vuitton embroidered bib, shirt, pants, and shoes 

WHAT: 30th annual Palm Springs International Film Festival Film Awards Gala

WEAR: Thom Browne suit

WHAT: The Academy of Motion Picture Arts and Sciences 10th annual Governors Awards 

WEAR: Haider Ackermann suit

WHAT: 22nd annual Hollywood Film Awards

WEAR: Louis Vuitton shirt and suit

WEAR: UK Premiere of Beautiful Boy at the 62nd BFI London Film Festival 

WHAT: Alexander McQueen suit

WHAT: Amazon Studios premiere of Beautiful Boy at Samuel Goldwyn Theater 

WEAR: Louis Vuitton suit and shirt

WHAT: Beautiful Boy premiere during the 66th San Sebastian International Film Festival 

WEAR: Alexander McQueen suit

WHAT: The Hollywood Foreign Press Association and InStyle Party at the 2018 Toronto International Film Festival

WEAR: Haider Ackermann blazer

WHAT: 2018 Toronto International Film Festival

WEAR: Haider Ackermann suit

WHAT: 90th annual Academy Awards 

WEAR: Berluti suit

WHAT: 90th annual Academy Awards Nominee Luncheon

WEAR: Gucci suit

WHAT: Call Me By Your Name premiere at UGC Cine Cite des Halles in Paris, France

WEAR: Berluti leather jacket

Looking for the other best dressed men of 2019? We got you covered. 

Opening Image: Mike Marsland/WireImage

Anyone who knows me understands that I am a die-hard feminist (you can always find me bumpin’ Beyoncé’s "Formation"). But don’t let that fool you—I am so here for men too, especially those with indisputable style. My support of equal rights does not preclude my ability to recognize the fire fits I've spotted on Hollywood’s leading men this past year. In many ways, we can consider these men the unsung style heroes of 2019 because of their embrace of camp, which was also notably the theme of this year’s Met Gala. 

Camp's origins can be traced back to 17th-century France; Molière even created a term about it, "se camper," which means "to pose in an exaggerated fashion." From striking a pose to its current usage as a descriptor for some queer men's style, camp fashion, aka dramatic style, isn't just for the few. It's for everyone who doesn’t care about holding up patriarchal beauty standards. This year more than proved that. 

Seeing men publicly embrace the spectrum of style, from feminine-inspired red carpet looks to power suiting to grunge galore is a reminder to us all that true style has no gender. Because why hold on to the antiquated notion that men shouldn't wear pearls or paint their nails or care about their clothes at all? There’s something that empowers people of all gender identities when you can break the boundaries of style and look damn good doing it. Ahead, enjoy scrolling through 19 of the best dressed men of the year whose style had my edges snatched throughout 2019.

#19. Keanu Reeves

Let’s be honest: This year was rough, but it did bless us with the resurgence of heartthrob Keanu Reeves and his minimalist style that verges on maximalist for the sheer fact that he looks so good in all-black ensembles. His campaign with Saint Laurent earlier in the year was a reminder that like a fine wine, this man and his style only get better with age. 

#18. Cole Sprouse

If I didn’t include Cole Sprouse in this list, I would have suffered consequences from fellow editors (*cough, Lauren Eggerston, cough*). Despite potential repercussions, this particular Sprouse twin has come into his own this year, which makes him oh so worthy of being included on this list. Yes, I love Sprouse in a good beanie and shearling jacket (his signature Riverdale look), but let’s be real here: He shines in a non-traditional suit, and this Paris Fashion Week look is no exception. 

#17. Hasan Minhaj

Comedian Hasan Minhaj’s style is a bit more traditional, but honestly it’s refreshing to see a man who values his suits as much as his sneakers—and trust that Minhaj knows the style cred of both. While this year’s wardrobe included quite a few non-traditional suit looks that weren’t a laughing matter, I particularly loved this forest green tuxedo he choose to wear to the CFDA Fashion Awards—it’s like the beginner's suit for embracing camp for men: no sequins were hurt in the process, but it’s still extra.

#16. Henry Golding 

Henry Golding captured a special place in my heart (and the hearts of many) when I first spotted him onscreen back in 2018 as the protagonist in Crazy Rich Asians. And while the actor continues to be America’s on-screen rom-com crush,his style continues to fuel my minor obsession. I have yet to see a suit that does not look good on this man—please show me a bad picture of him, I beg of you. Side note: More men should volunteer to wear velvet in 2020. 

#15. Michael B. Jordan

Life, or any listicle for that matter, is not complete without Michael B. Jordan. Sure, he’s incredibly handsome, talented, and has collaborated with Coach for a unisex line, but don’t let that detract from the most important fact of all: His suit game leaves me in shambles. Specifically, this look for the 25th Annual Screen Actors Guild Award; the suit, paired with a Louis Vuitton harness, was quite the controversy. But, in an unpopular opinion, I am here for men gracing the red carpet with a harness look, especially if that man happens to be Jordan, Chalamet, or Maluma.

#14. Maluma

You’re not going to change my mind about this: as previously stated, I am here for men in harnesses. I am also very much a fan of Colombian singer Maluma. If you don’t know him, then he’s a man whose style and music should 100% be on your radar. I confess, I didn’t know much about Maluma until I stumbled upon his most recent feature with GQ, but once I fell down the hole, I fell hard, and you will too. His style is always exploratory, he had some bops, and he’s easy on the eyes—aka, he's the perfect contender for being one of the best dressed men of 2019, and for stealing your heart.

#13. Charles Melton

I don’t know what’s in the water on the Riverdale set, but the men on that show know how to dress—case in point: Charles Melton. The Korean-American actor has a knack for putting together the type of looks you wish you or your S.O. thought of first—like the Paris Fashion Week look above. But beyond his off-duty style, he’s not the type of man to shy away from wearing a glitter suit to the Met Gala, which is what we need more of in the world. 

#12. Donald Glover

One could say that Donald Glover is the archetype of the unconventional creative. From his award-winning show, Atlanta, co-starring the brilliant Zazie Beetz, to his most recent movie with Rihanna, Guava Island, this man’s artistry is always moving the culture forward. So of course you can expect nothing less from his style. Case in point, the pussy-bow blouse paired with a floral jacket and heeled loafers he wore to the LACMA Gala this year killed me.

#11. Machine Gun Kelly 

While grunge is a trend for some this fall, that’s rapper Machine Gun Kelly’s whole damn aesthetic. He's known for his angsty, genre-mixing music, and in many ways, his art speaks to his style too. His ensembles are this tantalizing, hard-to-define mix of rock 'n' roll bad boy meets non-binary—just look to the zebra coat he wore for a performance this year. Um, why aren’t men wearing more statement coats and leather pants? And can I pull off this look?

#10. Tyler, the Creator 

Music is not the only thing Tyler, the Creator is innovating. What is particularly remarkable about this artist is that he’s never been afraid to push the boundaries with his style—it’s like a Supreme stan meets grandpa in the best possible way. How many other male artists do you currently seeing rocking blonde wigs on tour with ease? Tyler’s style is a rebuke of cool, the cliché, and most of all, it’s a call to action for men and women to redefine what’s socially acceptable when it comes to style.

#9. Jaden Smith

This may be an unpopular pick, but I know in my soul that Jaden Smith is going to be the poster child for the evolution of men’s fashion. A suit will never go out of style, but what makes Jaden—and the evolution of menswear—so exciting is that exploration of the spectrum of style. I hope more men feel free to explore in this way. Dye your hair pink, pair your black suit with a colorful scarf, add a lil’ Dr. Marten to your tuxedo—the world is your fashionable oyster, especially if you’re Jaden Smith. 

#8. Timothée Chalamet 

Speaking of poster children, aside from the Louis Vuitton glitter harness look Timothée Chalamet blessed us with at the Golden Globes, Chalamet didn’t stop serving us looks this year. Picking a favorite was like pulling teeth because the actor’s style is the remedy for my sweet tooth. That said, jaws dropped everywhere when he showed up in a fitted light gray belted Haider Ackermann suit and cowboy boots at the Venice Film Festival this year. 

#7. Bad Bunny

Anyone sleeping on the Puerto Rican musician Bad Bunny is committing a crime. Not only has his music been dominating the Billboards, but his style on the gram is fuego, fuego, fuego. Bad Bunny never ceases to push the boundaries of non-conformity; from street-wear–inspired looks to grunge, what can’t this man pull off? And I’m sorry, but do you see how his nails are coordinated with his hair color for the Billboard Latin American Awards red carpet? Shooketh.

#6. Harry Styles

While some of the haters of the world questioned Harry Styles’s camp-inspired Met Gala look, I was so here for it. Yes, honey—not only can he rock a Gucci suit or some wide-leg trousers, but he has also truly reminded us that the best looks often eschew society's gender norms. More men wearing pearls in 2020, please.

#5. Lil Nas X

Billboard records weren’t the only thing Lil Nas X was breaking this year—in fact, his style was equally as genre-bending. From his digital cover of Teen Vogue to his Killa-inspired Halloween costume, Lil Nas X has been having a banner year. But the moment that really solidified him as one of the best dressed men of the year was when he showed up to the MTV Video Music Awards in a full-on, Prince-inspired glitter look. Can’t nobody tell me that Nas wasn’t a style icon in 2019.

#4. Ezra Miller

There would not be a complete list of men pushing the boundaries of style without Ezra Miller. The internet lost it when he rolled up in his head-turning Met Gala look, and since then, he has proven that makeup, florals, and all things "feminine” ain’t just for the girls. I mean, just look at this cat eye he wore to the launch of Urban Decay’s stayNAKED launch—his makeup skills are better than mine will ever be, and I’m not mad about it. 

#3. A$AP Rocky

Not playing favorites here, but A$AP Rocky is one of the most stylish men of all time. I often think about when Rocky sported a Gucci scarf around his head like a grandma to LACMA’s Film Gala, not just because it was a look, but because from day one he has been on the camp bandwagon. In many ways, Rocky’s style re-established the correlation between masculinity and experimental fashion for not only black men but all men. Because true masculinity is being comfortable enough to wear a Dior tank top, or dress like a babushka and know that it has nothing to do with your sexuality.

#2. Jared Leto

Jared Leto has always been a non-binary style icon: Case in point, some of his iconic looks this year included him wearing a pink fur to Gucci’s show or his LACMA Gala look. But the look that really turned heads, and encapsulates the fact that 2019 was the year of men pushing style’s boundaries, was his jewel-encrusted Met Gala look. If this outfit isn’t mind-blowing, then I don’t know how you’ve managed to scroll this far. 

#1. Billy Porter 

And finally, the moment you’ve been waiting for: Number one on our list of the most stylish men of 2019 is the one and only Billy Porter!  No red carpet, or expectations of what men can and can not wear, will ever be the same thanks to this Broadway icon. The activist and actor shut it down this year; not only did he stun us at the Met Gala and pull off wearing a dress to the Oscars, but he became the first openly gay black man to win an outstanding lead actor in a drama series Emmy for Pose. Basically, 2019 was Billy Porter’s year, and we were all just living in it. Frankly, that’s not a bad thing in my book. 

Next: From Tracee to Rosie, the Best Celebrity Outfit Posts of the Year (So Far)