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.

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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.

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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.

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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.

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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.”

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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?

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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.

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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.

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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.

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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.

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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.

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

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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. 

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

This post originally appeared on Who What Wear US. 

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

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