Between jelly sandals, Carolyn Bessette-Kennedy-inspired fashion and statement cord necklaces, it feels like the ‘90s are officially back. But let’s be honest, this iconic decade has never really left us. But it’s undeniably more evident in 2026. And if there’s one nineties category that made the biggest mark this year, it would certainly have to be beauty. More specifically, '90s makeup looks are making a huge comeback this year, with some of the biggest trends being those we saw dominate almost four decades ago.

Now, we know that makeup trends come and go, especially in the age of TikTok, Instagram and YouTube, but there’s just something about a ‘90s makeup look that feels timeless, fitting right into the current zeitgeist without a second thought. Of course, there are trends that, as a makeup minimalist, would have had me running in the opposite direction: body glitter, bright blue eyeshadow and face gems, to name a few. But luckily for me, the it-girl-approved ‘90s makeup trends making a comeback in 2026 remain chic, timeless and, most importantly, feel extremely wearable.

Below, I’ve rounded up the seven key ‘90s makeup aesthetics that are set to dominate 2026. From playful pops of colour that are perfect for the upcoming summer season to the dark lip-liner trend that’s taken TikTok by storm, keep scrolling to see the ‘90s makeup looks trends that are making a comeback in 2026, plus the best beauty buys available so that you can get the look at home.

1. Statement Red Lip

We can't talk about '90s makeup without talking about a bold red lip. Unlike in the current day and age, when it's often paired with equally eye-catching smoky eyeshadows and statement blushes, in the ‘90s it was all about keeping the rest of the face pared-back and minimal, so as to let the lips do the talking (pun intended).

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2. Colour Pop

Vivid eyes, cheeks and lips were certainly all the rage in the '90s, and I can see why. These playful colour pops take a makeup routine from basic to elevated, and although I’m not ready to go all out with the trend, this pretty pinky-purple look on Naomi Campbell is slowly convincing me to try it out.

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3. Frosted

With “cold-girl makeup,” one of TikTok's latest obsessions, it should come as no surprise that the frosty aesthetic is making a comeback this year. Available in the form of everything from lipsticks to eyeshadows to highlighters, this icy makeup trend perfectly balances feeling cool and classic.

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4. Ultra-Matte

As someone with extremely dry skin, I’ve always been skeptical about recreating the ultra-matte bases that dominated the mid-90s. However, there are now plenty of products that give that blurring effect without sucking out every bit of moisture from the skin. So, I’m ready to give this long-lasting, sophisticated look a try.

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5. Dark Lip Liner

I’m not trying to brag, but I’ve been rocking the dark lip liner trend since I was a young teen. Between ultra matte blacks, cool-toned browns and deep burgundy hues, this is a trend that I can guarantee will never date.

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6. Ultra-Thin Brows

If you have thin eyebrows as I do, then you’ll be pleased to know that the ultra-thin brow trend, championed by the likes of Victoria Beckham, is officially back for 2026.

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7. Smoky Eye

For those more formal occasions, there’s nothing quite like a smokey eye. Although this mesmerising eyeshadow look has technically never stopped trending, I, for one, will be taking a cue from the likes of ‘90s icons such as Cindy Crawford and recreating this more subtle look for summer evenings out.

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Growing up, Britney Spears influenced my music taste more than any other artist. I'd beg my parents for each one of her new CDs, and when I got them, I'd play them over and over again until the reflective coating was almost completely scratched off. One of my fondest memories is when my parents gifted me her self-titled Britney album for Christmas. I stayed up listening to it with my ear pressed against my pink boom box, so as to not wake my parents who were sleeping down the hall. 

I still occasionally listen to my favorite songs (Cinderella, Overprotected, and Lonely among them), but I consider my Britney days to be mostly behind me. Or, at least, I thought I did. As it turns out I'm still being influenced by Britney Spears—except now I'm being influenced to buy beauty products instead of listening to the same song five times in a row. I just found out which shampoo she uses, and it's under-$20, eco-friendly, and in stock on Amazon. It's even discounted for Cyber Monday, so I couldn't help myself but place yet another Prime order. 

Instead of a traditional liquid or gel formula, Spears reportedly uses the plastic-free shampoo bars from Ethique. While we're not sure exactly which one she uses, there are multiple scents and formulas to choose from—like this minty one that uses peppermint oil, Ghanaian cocoa butter, and organic creamed coconut butter to refresh, moisturize, and cleanse hair without weighing it down. 

These shampoo bars are cruelty-free, plant-based, and made with sustainable and ethically sourced ingredients (oh, and there's no palm oil either). What's more is that each one is packaged in plastic-free, home-compostable cardboard. So yeah, they're probably some of the most eco-friendly shampoos on the market.

The best part is that using them is easy and they last up to 80 washes. Simply wet your hair and the bar, massage the bar into your roots, and lather. That's it. From there, just follow up with a conditioner. (I have some recommendations for you, but more on that in a minute.)

This one is safe for color-treated hair and uses mango seed butter, peach kernel oil, and rice powder to balance the hair and scalp. It also adds shine and bounce. 

If smoother hair is your goal, this one should help. It's deeply moisturizing to restore shine. 

Personally, I think Spears would approve of this one. It's formulated to balance the hair and scalp (in other words, it hits the sweet spot between dry and oily) and is scented with sweet vanilla and zesty grapefruit. I don't know about you, but to me, that sounds delightful. 

If you have blonde hair like Spears, this one might be for you since it helps keep brassiness at bay. The purple pigment (from naturally occurring sources like beetroot powder) counteracts yellow and orange tones to keep blonde and silver tones bright. 

Shop the Brand's Conditioner Bars

Welcome to our podcast, Who What Wear With Hillary Kerr. 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 Who What Wear With Hillary Kerr on Apple Podcasts and Spotify.

Los Angeles–based stylist and designer Alejandra Hernandez knows how to make a smash hit.

Recently, Hernandez's work was in the headlines when she styled SZA in a Princess Diana–inspired photo on the cover of her latest album, SOS. Surprisingly, Hernandez didn't know which look would make the final cut in the cover artwork until a few minutes before the public did.

In addition to her work with SZA, Hernandez has worked with the likes of Iggy Azalea, Eve, and Britney Spears. She is also the designer for Year of Ours, the female-led activewear and lifestyle brand.

In the latest episode of Who What Wear With Hillary Kerr, Hernandez shares how all of the looks came together for SOS, the differences between preparing for editorials and music videos, and more.

For some excerpts of their interview, scroll below.

Can you tell me a little bit about how you started out and eventually found your way into both parts of your fashion career?

I grew up in L.A., and I always knew I wanted to be a fashion designer. When I was a kid, I didn't know what being a stylist was. We had a family friend who was a costumer, and she was my childhood hero. Because that was the closest thing I knew to what I wanted to be.

I always wanted to be a fashion designer, and my goal was to go to FIT in New York City right after high school, but September 11 happened, but that derailed my moving to New York City.

I did a semester at SMC [Santa Monica City College], and then I went to FIDM. I went for fashion design. I had a teacher—I even remember her name; it was Mrs. Owens—and she was a designer. She actually had just gotten a job as head designer of Apple Bottom jeans.

She was portfolio teacher, and I remember she told me that I would be a good stylist. She had previously worked at MTV as a stylist, and she introduced me to what that was because I didn't really know what it was. I interned for her at Apple Bottom after I graduated. Then I interned at a few different denim companies. I eventually got a job with a small L.A. brand as women's designer, and I was there for four years.

There, I met stylists, and I started assisting. I did freelance design after I left, but I focused more on styling.

I read that your folks were both hugely influential in your career for a number of reasons. Your mom is from Peru and is a jeweler and that your dad is from Argentina and used to sell 501s and other American-made denim brands at his store before immigrating to the U.S., but that they did not fully understand your career and what you were doing for a number of years. Can you tell me a little bit about that?

I think they both were influential, and they both really inspired me because they're both very entrepreneurial. Neither of them had a formal education in business, yet they both did well for themselves. That kind of showed me that I didn't have to have a formal education in business even if the business is myself. You know what I mean? I consider myself a business. They helped me in that way, for sure. They always supported everything I wanted to do.

Culturally, it's something that I think a lot of first-generation Americans experience when we work in creative fields or we work in American mainstream media. Our parents are not in tune with American pop culture. They don't care. My parents are really Latino. They are still listening to Latin music. I could be doing the coolest video that got a million views in 10 seconds or something, and I'd show my dad, and [he'd] be like, "Oh, yeah, that's nice."

My sisters have master's degrees and are working on their PhDs. They're just such accomplished scholars. I know they're proud of me, but it took a while I think for them to fully understand that what I was doing is cool, too.

You've worked with all kinds of interesting folks, from Iggy Azalea and Eve to Britney Spears. Most recently, you have been ushering in a new fashion era for the one and only SZA. I'm curious about how the two of you first connected and started this collaboration.

The first time I worked with her was actually on her "Drew Barrymore" music video. Then I started working with her again at the end of 2018, so that was the beginning of our working. I think we became friendly after the "Drew Barrymore" video but really working together was at the end of 2018.

I'd love to talk about the album artwork with that cover graphic that was inspired by that iconic shot of Princess Diana. That photo of Diana on the diving board looking into the sea and then the interpretation of that and elevation of that for the cover has generated a lot of conversation and love online. Did you have that whole vision in your mind? How did the jersey come about? Were there other options?

There were other options, including one custom jersey that we made on set that we pieced together different jerseys, and we made this reconstructive jersey.

There were different options and with different combinations with different shoes. There was also swimwear that we pulled just in case. She didn't even try it on, because I think, like I was saying earlier, she's always right. In the end, it wouldn't have been so amazing if she would have worn anything that would be expected.

You see that photo, and you know it's a Princess Diana reference, but she's herself on it, which is also symbolic. If it would have been anything else, it wouldn't have been as amazing.

I didn't know which one was going to end up as the cover artwork until probably like 30 minutes before the public did, when we saw the picture!

To hear the entire interview, tune in to the podcast, and to shop favorites from Alejandra's latest collection with Year of Ours, keep scrolling. 

This interview has been edited and condensed for clarity. Next up, check out our previous episode featuring Madelyn Cline.

There’s no doubt that Britney Spears’s style is the stuff of pop culture legend: the bright red catsuit from Oops. . . I Did It Again, the schoolgirl outfit in . . . Baby One More Time, Toxic’s blue flight attendant ensemble. Each has launched a million Halloween costumes, perhaps the ultimate barometer for whether someone’s style is emblazoned on pop culture iconography.

The list of Spears’s legendary looks, whether on the stage, in a video, or on the red carpet (never forget the matching denim-on-denim with JT) is endless. What’s less talked about is how Spears popularized a number of trends that now define Y2K style, like the bubblegum vibrancy of the color palette and bedazzled, glitter-strewn embellishments.

What’s unique to Spears are the elements of ’70s boho style that wove their way into many of her looks, although always with a Y2K spin. The early 2000s saw Spears in crop tops with bell sleeves, baby tees worn under shearling coats, low-rise flare jeans, and fringe pieces in multicolor hues. There was something about Britney’s happy-go-lucky, unpretentious style that made it appealing, and its vibrant youthfulness always retained a sense of fun that never took itself too seriously.

Ahead, we’ll review some of Spears’s more underrated looks that further cement her as one of the great style icons of the past 20 years.

We could never say to no to a neon moment, particularly when paired with a patterned miniskirt.

Yes she dared to rock the crop top with a low-rise skirt, as she should.

Sequined top? Check. Sequined pants? Check.

The sleeves, the buttons, the color… this top is total Y2K eye candy.

These long, fur-trimmed cardigan-coats need to make a comeback. And yes, we see the butterfly boots.

Boldly taking orange where few dare to tread.

LBD, but make it quintessentially Britney Spears.

Black-tie glamour from Ms. Spears.

Snakeskin pants in aqua blue? Don’t mind if we do.

Deep cowl necklines are a repeated motif in Spears’s 2000s looks.

The purple fringe, the teal necklace—we love it all.

A more pared-back moment for early-2000s Britney.

This fuschia color is so stunning, but the beading takes it to the next level.

The halter neckline, layered chain belt, and acid-wash flare jeans make this the outfit of our preteen dreams.

We could never say no to a corset dress. This gorgeous lacy-blue number with the floral shawl is perfection.

Spears turns the bedazzled meter up to ten.

The corset top trend had a huge moment in the early 2000s.

There’s just something about the pink-on-pink with the cargo pants.

Those boots! Spears ventured into neutrals more than expected in the 2000s.

The pageboy cap and dress-over-jeans combo is too nostalgic.

You don’t need to layer when the coat speaks for itself.

The sheer organza jacket is such a whimsical detail. Side note, who didn’t love Spears's short bob moment around 2000.

Tracksuit, but dress it up. The orange shades are also a must.

Congratulations are in order for Britney Spears and her longtime boyfriend, Sam Asghari! The couple, who have been dating since 2016, expressed the desire to get married and expand their family but faced numerous obstacles due to Spears' ongoing legal conservatorship.

Moments ago, Spears posted a sweet video on her Instagram account with the caption, "I can't fucking believe it 💍💍💍💍💍💍❣️!!!!!!" Asghari shared a cheeky photo as well, captioning it only with the king and queen emojis.

Recently, following much media attention, Spears' extremely restrictive conservatorship was revoked, allowing the couple to pursue regular activities such as riding in Asghari's car, and, most recently shopping for engagement rings earlier this month.

According to Page 6, New York City–based jewelry designer Roman Roman Malayev created the one-of-a-kind ring that Asghari used to pop the question. Set in platinum, the 4-karat round, brilliant-cut stone is enhanced by its cathedral setting which creates a floating appearance.

Keep scrolling for a look at the beautiful ring, and photos of the happy couple.

Next: Lily Collins Just Got Married in a Fairytale-Worthy Wedding Dress

Ah, the '90s. An era defined by MTV, halter-neck tops, and more boy bands than we care to count. Some of our absolute favorite pop culture moments were born out of this decade, and when we think back on it, we can't help but relish in the wonderfully wild '90s hairstyles. And with the boom of the Y2K trend that we've seen over the last few months, it seems we're not the only ones who are feeling a little nostalgic.

From messy buns to a broad selection of fringes, and, of course, butterfly clips galore, there was something special about the hair trends from this time. The It girls of the era, such as Britney Spears, Janet Jackson, and Gwen Stefani, were serving up enough inspiration to carry us right into the following decade.

If you're as nostalgic as we are, then you'll love this roundup of the 20 most quintessentially '90s hairstyles we would low-key wear today. We might get some strange looks, but hey, we'll never shy away from an adventurous beauty look. Keep reading for our favourites.

20 of the Best '90s Hairstyles

1. Tiny Twists

The only thing that could make this style more '90s is a mini clip placed at the end of these tiny twists. This half-rolled hairstyle, also dubbed "picture-day hair" by the primary school set, ruled the decade.

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2. The Winona Pixie

The subtle layers and laid-back styling made this pixie cut an instant hit when Winona Ryder debuted it in the late '90s.

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3. Micro Braids

No one rocked micro braids quite like Brandy Norwood. This was her signature hairstyle on her hit TV show Moesha as well as in her real life.

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4. Bumped Bob

The soft curl added to this classic bob adds an interesting element to the hairstyle. Shown here on an angelic-looking Angelina Jolie, this spin on the bob would make us do a double take if we saw it walking down the street today.

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5. Feathered Fringes

There was a period of time when it seemed like every TV character was sporting these voluminous, feathered fringes. From D.J. Tanner to Kelly Bundy and, of course, Tiffani Thiessen's Saved by the Bell character, Kelly Kapowski, these bangs were the mark of a cool girl.

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6. Claw Bangs

On the other end of the fringe spectrum were these claw bangs, defined by face-framing, peekaboo pieces.

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7. Teeny Double Dutch Pigtails

This easy hairstyle screams '90s. Britney Spears fashioned her short haircut into two messy plaits fastened on the ends with elastics and just enough hair peeking out of the bottoms for a playful 'do.

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8. The Flip

From the pencil-thin eyebrows to the dark lipstick and the leopard-print collar, this photo of our queen Drew Barrymore is like a time capsule into the '90s. Her flipped hair (and those enamel hair clips) is another huge clue as to which decade we're looking at.

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9. Bedazzled Bandanas

Okay, so in all fairness, this photo was taken in the year 2000. But it's important to call out here because it exemplifies the influence that '90s hip-hop had on style and culture well into the decade that followed. J.Lo's bedazzled bandana accentuating her braided hairstyle is proof.

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10. Jumbo Box Braids

Janet Jackson's braids circa Poetic Justice were (and still are) a legendary look. The addition of this newsboy cap solidifies it as one of our favourite looks of hers.

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11. Butterfly Clips

Stefani wasn't afraid to push the envelope when it came to hair. But here, we see her adopting a trend that took hold of just about every '90s girl: the infamous butterfly clip. It was such a thing.

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12. Shortest Possible Platinum Pixie

Jada Pinkett Smith showed us plenty of short haircuts in the '90s, but this bleach-blonde, barely there cut was one of our faves.

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13. The Hilary Banks

Everything about The Fresh Prince of Bel-Air is a perfect representation of '90s life, but nothing compares to Hilary Banks's perfectly coiled coif, which she'd often top with a statement hat or oversize bow to tie her ensemble together.

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14. Messy Bun + Wispy Tendrils 

Don't be fooled by the name: The messy bun could be a super-chic look. Paltrow proved this point on a '90s red carpet, where she kept with the undone theme by letting some face-framing curls hang loose.

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15. The Rachel

Do we even need to explain? Didn't think so.

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16. The Sky-High Pony

Leave it to supermodel Tyra Banks to claim even more height with this sleek high pony. The flipped curl and swooshed bang add that much more '90s flair.

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17. Antennae

Nineties girls were all about an undone look, as evidenced by the trend of leaving just two straight strands of hair out in the front of an otherwise polished style.

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18. Two Braids

In an era marked by plenty of grungier looks, this almost childlike style really stood out. Note the clipped bangs as well.

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19. Chunky Highlights

Apparently subtlety just wasn't in style in the '90s. Kelly Rowland's highlights, coupled with her choppy cut, were clearly meant to stand out.

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20. Scrunchies

Scrunchie madness was such a defining trend of the '90s. They were perfect for securing any kind of ponytail or even just wearing around one's wrist like a bracelet. You know, just in case.

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This story was originally posted on Who What Wear US and has since been updated.

I don't know about you, but I'm hanging on to summer for dear life. I'm simply not ready to say goodbye to the sunny season and prepare for fall. Perhaps I'm also secretly dreading my 30th birthday next month? Well, I happen to know at least one other person who feels the same way: Britney Spears. She's been 'gramming up a storm from her summer beach vacations, and her bikini-clad content shows no signs of slowing down. 

In her newest Instagram post, Spears let us in on a little secret. Even though she could access all the designer swimwear in the world, she chooses to buy cheap bikinis from Target aka the one and only place I shopped for swimsuits growing up. While Spears's exact bikinis are sold out, scroll down to shop other affordable Target versions that are just as cute.

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Next: Is It Just Me, or Does Every Celeb Own These 4 Cult Fashion Items? 

Deep-scrolling through TikTok or a trend guide cements one fact: Y2K fashion is back. Sure, we may still be slightly traumatized by low-rise denim and exposed G-strings, but it’s all part of the moment. What makes a trend "of the moment” moves far beyond the cyclical nature of fashion. A bevy of things is required to make it happen. No one was thinking about going near anything aughts-related until it was trending on TikTok or championed as the Hot Girl Summer aesthetic by rappers like Megan Thee Stallion. But beyond the social influence, historically speaking, after any form of mass upheaval—pandemics, warfare, or recessions—clothing becomes, well, over-the-top. (See the recent rise in risqué trends.) This is why I’m placing bets that the next big trend will be rhinestone swimsuits. 

Sparkly swimsuits in every form—embellished, sequin, chain-mail, and rhinestone—had a hold on us in the Y2K era. There was one point in fashion history when runways, red carpets, films, and private islands were filled with celebrities wearing itty-bitty rhinestone bikinis. But the case for bringing back blinged-out rhinestone swimwear was unwarranted… until now. If you’re not convinced, ahead we’re showing how rhinestone swimsuits (and other examples of embellished swimwear) were the epitome of peak-aughts style, how they’re coming back, and where to buy the 2020s version now.

For the newbies in the back, the late ’90s and early ’00s saw big fashion brands burgeoning with risqué trends. But the most exciting moment was when, suddenly, women were wearing rhinestone swimsuits. Of course, it didn’t just come out of nowhere—brands like Baby Phat and Chanel finished off iconic runway shows with Lil‘ Kim and Naomi Campbell in rhinestone-encrusted swimsuits. High fashion was not the only place where glitzy swimwear shined. Britney Spears and Jennifer Lopez donned various iterations of sparkly swimsuit tops paired with matching bottoms on stage. Yet the most iconic (albeit questionable) styling of these embellished bikini tops was when they emerged on the red carpet at A-list events. Everyone from Destiny’s Child to Gwen Stefani wore heavily adorned, crystal, and chain-mail bikini tops with denim skirts and second-skin tops. It made the case that skin was not only in but that swimwear didn’t need to be worn exclusively near a body of water. And if that’s not the most aughts thing ever, I don’t know what is.

At some point, as rhinestones became overdone (much like the embellished jeans and trucker hats from iconic 2000s fashion brands like Ed Hardy—ah, memories), the rhinestone swimsuit was replaced by more classic swimwear. Post-pandemic, however, celebrities are slowly bringing back embellished swimsuits for seemingly every occasion. Think of Kim Kardashian West’s viral re-creation of Elle Woods’s Harvard Law admissions video from Legally Blonde or Dua Lipa’s incredible 2021 Grammy Awards look. Somehow, this bejeweled look is back. 

But before you pass on this blast from the past, we’ve taken the liberty of rounding up the best rhinestone swimsuits on the market right now (along with a few sequin, crystal, and chain-embellished ones) to help you embrace your sparkle and bring this Y2K trend back in style. 

Shop the best rhinestone swimsuits:

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Next: A Celeb Stylist Ranks the Biggest Fashion Trends of the 2000s

You might think Instagram sparked the golden age of manicures. But looking back, it turns out the early aughts walked so the 2010s could run. The new millennium started out with some late-’90s mall relics like frosted polish and French manicures but became more adventurous as time went on when Chanel’s gone-but-never-forgotten Black Satin polish hit the scene. And things just got more over-the-top from there.

But like so many other nostalgic fashion and beauty trends, we suddenly want to wear them all over again. In fact, the biggest nail trends of 2021 are remarkably similar to those that took over 2001. To prove it, we’re taking a walk down manicure memory lane with Brittney Boyce, celebrity nail artist and founder of Nails of LA, and including ways to re-create the looks right this second. Best of all, the polishes and products of this decade are much healthier for our nails and a little more, well, polished overall.

The French manicure was the go-to for celebs like Jennifer Lopez but then faded into obscurity. "For a long time, white tips were almost forbidden and seen as dated and tacky,” says Boyce. "But with almond or round shaped nails, it looks really updated and classic. It’s back to the original intent of the look, which is to accentuate the look of a natural nail for film, runways, and photos by elongating the look of your hands.”

This Y2K-era trend, seen here on Mya, gives us all the feels. "Frosted nail polish is very easy to do when you’re busy and don’t have time for extensive nail art. I love the jewel tones,” says Boyce, adding that the trend "looks better on short, natural nails.”

In the early aughts, long acrylics were a celebrity favorite, with everyone from Missy Elliott to Pink wearing the look. And although natural, short nails had their moment in the 2010s, longer nails have had a resurgence in the last five years or so. "I’ve never been a big fan of acrylic, as it’s harsh on the nail, but I am a big fan of gel extensions, which is the modern way of achieving length without damaging your nail,” says Boyce. "I think good nail extensions look super sick!"

The punk staple went mainstream after Chanel Black Satin became the It nail color, and everyone from Jessica Simpson to Lauren Conrad wore the shade. 

Kimora Lee Simmons’s flip phone may be totally 2000s, but her nail color will never be out of style. "I did a hot pink recently for Megan Fox for the iHeartRadio Awards, and it was really fun,” says Boyce.

If you spent algebra painting Wite-Out onto your nails, you found your next mani shade. "White nail polish looks really great in the summer,” says the nail pro. "I also like using the white base as a canvas for nail art.”

The nail-art bubble may have burst in the last decade, but it’s been around forever. Fergie showed off this entry-level take back in 2005. "I always love minimalistic graphic nail art. It’s like modern art meets nails,” says Boyce. "In 2021, I think a graphic nail looks great with color-blocking.”

Gwen Stefani’s vintage-inspired phase brought lots of red lipstick and nails. "I think classic red will never go out of style,” says Boyce.

From cell phones to sunglasses, "bedazzling everything was really big in the 2000s,” Boyce reminds us. The wearer of this crystal-embedded manicure? None other than Serena Williams, who is a certified nail technician(!).

"The reverse French with clear tips started coming into the scene in the early 2000s, and it’s one of my most requested looks nowadays,” says Boyce of looks like Christina Aguilera’s. "But now we amp up the clear tips more by using a thin metallic shade to show the separation.” 

And now: The 20 Best-Selling OPI Nail Colors of All Time—That You Can Still Buy

After several years of all things ’90s retaking fashion and beauty trends, it seems a natural progression that the 2000s followed suit. But if the ’90s were known for sleek, minimalist looks, the decade after them was known for just the opposite. "Hair in the 2000s was wild because everyone was trying to do something a little different that no one had seen before,” says celebrity hairstylist and Color Wow artistic director Joseph Maine. "There were really no limits and people were experimenting with different textures and accessories. It was a playful time for style.” And playful is right. From dramatic hair colors to iconic (and unique) haircuts, hair in the early aughts was in a beauty league of its own.

Although some of today’s fashion icons like Bella Hadid and Megan Thee Stallion are no doubt inspired by this time in fashion and beauty history, it’s evident that some styles may stay firmly in the past. Keep scrolling as we look back at 20 of the most memorable looks from the era (crimping included!), along with Maine’s expert insight.

Lopez famously topped off her braided hairstyle at the 2000 MTV VMAs with a white bedazzled bandana that matched her outfit. 

We couldn’t help but wonder… if SJP hadn’t let her natural curls run loose, would Carrie Bradshaw’s style—and in turn, Sex and the City itself—be so iconic?

Berry’s is arguably one of the all-time great short haircuts from any era. "That pixie cut will really never go out of style, especially if you have the bone structure that Halle does,” says Maine. 

Good news for Kelly: Her two-tone hair color is making its way back again, with celebs like J.Lo and Dua Lipa wearing the look recently. 

Good news if you still love Avril’s slick-straight look. "Straight, glossy hair really never goes out of style,” says Maine, who recommends using a smoothing treatment like Color Wow Dream Coat ($30) "to give thermal protection and add a ton of shine.”

The late singer-actress was ahead of every trend she wore, from her ombré hair color to her deep side part—a look that dominated the decade (sorry, Gen Z).

"This was an iconic hairstyle that was rarely replicated well,” says Maine of Aguilera’s multitonal look. "The sort of preciseness and choppiness of the cut and extensions helped give this a bit of edge.”

The crimper may have peaked in the ’80s, but it held on through the early aughts as evidenced by Tyra (and her smize).

Brandy’s contributions to millennium-era prom styles can’t be overstated. Case in point: This gorgeous upswept braid bun, which would have looked perfect for the occasion.

She flirted with pink, blue, and even brunette, but Gwen’s bleach blonde was one of the most iconic hair colors of the time (it even caught the attention of Martin Scorcese, who gave her the role of Jean Harlow in The Aviator). 

The rapper made her signature short haircut even more of a statement look by dyeing it shades like lavender and red to match her red carpet looks.

Keri’s haircut in season 2 of Felicity caused ratings to drop, as well as actual death threats. In hindsight, though, her character was going through a breakup (who hasn’t been there?), and also, she looked pretty great! 

The megastar has worn her hair in countless styles, but her long, Destiny’s Child–era waves set the tone for her look for years to come.

Don’t go pulling your Bump-It out of storage just yet, says Maine. "The poof is not coming back anytime soon," He says, however, "Pulling the fringe area back a bit more sleek is a great way to modernize this look and even add some fullness to the crown area.”

"The piecey bangs with some hair half-up is definitely back In style,” says Maine, adding that he’d leave "the additional peek-a-boo braids” back in 2000.

Seemingly every celeb wore this gravity-defying blow-out—extra layered hair required. Also, a moment of appreciation for how little Gabrielle Union has changed since this photo, from the 2001 NAACP Image Awards was taken.

For a brief moment in the early aughts, Farrah Fawcett’s iconic hairdo came back in style. Of course, Gisele pulled the look off with aplomb. 

This particular shade of dark red hair color only existed in the years 1999–2002. We don’t make the rules!

Along with her impossibly low-rise jeans, Brit’s love of headwear became one of her most notable style trademarks.

It’s the future she can see? With some slight styling adjustments, Raven’s Louis Vuitton logo scarf is just as in-demand today.

Blame LiLo for all our questionable side bangs circa 2003. Maine says it’s actually a great transition style: "I think side bangs are on the horizon with so many girls cutting curtain bangs recently,” predicts the hairstylist, adding that "The best way to grow them is by blending them into a bit of a side bang.”

Mischa’s O.C.-era waves would make Marissa Cooper proud. "This wavy texture is back in full force,” says Maine. "The best way to modernize this a bit is by using a waver with a [barrel] slightly larger than what Mischa used.”

Next, keep the early aughts flashback going with the 2000s fashion trends everyone will wear this year.

Gen Z Says is a series where we tap different members of Generation Z who will give us the latest insight on what's cool in the fashion space.

You've probably noticed that many trends from the early 2000s have resurfaced on the fashion scene—loved by some, controversial to others. While most of us may incorporate a colorful piece of jewelry or statement accessory inspired by the era, others have used that time period as a center point for their entire wardrobe and style aesthetic, like our very own WWW Gen Zer Devin Apollon. She showed off her nostalgic style as we kicked off the series, but now we're taking a deep dive into her personal style and why she resonates with the 2000s now more than ever. 

When you think of Y2K style, Paris Hilton may come to mind, but it really is the musical artists of that generation, from Destiny's Child to Britney Spears, who led the fashion trends. Anything those stars wore was destined to become popular alongside their musical hits. To this day, it's hard to think of that time period without singing along to "Say My Name" or "Toxic." To Apollon, that's what that era is all about, which is why she styled five looks inspired by some of the greatest songs of the 2000s that still resonate with her today. Keep scrolling to see her looks that will have you thinking you stepped into a time machine.

"Let's talk Aaliyah. Gone too soon, that's a fact, but she left an imprint on music, Black film, and R&B history. She also had one of the best (and most underrated) style moments of her generation. Aaliyah was always ahead of her time, and the few music videos she graced us with prove that. This song, in particular, just makes me feel so fresh, airy, and free. It is the musical equivalent of a sip of iced matcha on a hot summer day. It reminds me a lot of certain 'fits I put together when I want to be fresh and free but still cute. If you’re not up to speed on Aaliyah, I suggest you get there ASAP!"

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"This song? Princess of flirt activated. Heiress vibes are what I get from this song (and most of Mimi's discography, if I'm being honest). My love for the butterfly motif comes from Mariah. I love that she owns it in such a glamorous way. Mariah owns sexy silhouettes, sheer fabrics, and glitz in her wardrobe. This song is giving me the optimistic, vibrant mood that takes over my body whenever I'm involved in anything fashion. My remix would be called 'Clothes (I Need You)' by Dev."

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"Missy? Style icon. Musical genius. End of story. This song has cultural relevance so beyond Mean Girls, and it is an instant classic to me, my family, and so many friends. Stylistically, I have Missy to thank for the influence that baggy clothes, jeans, and sets have on my wardrobe. I obviously love being comfortable, but baggy works sooo well in fashion. My favorite trick is to pair baggy bottoms with a teeny top. It's super flattering and such an effortless look. Balance. Missy also has such a penchant for making hip-hop fashion. It is one of the most daring, yet rewarding, fashion crossovers."

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"If we have any era to thank for the camouflage trend in fashion, it is the early 2000s. (Thank you to the Army and Cady Heron.) Just as influential as camouflage was Destiny's Child, who had a choke hold on us all for the better half of a decade. I'm an original Destiny's Child superfan (which translated to my everlasting love for Queen Bey). Although, when I put these two early 2000s phenomena together, Meagan Good also comes to mind. For me, she is a Y2K red carpet legend and one of the best actresses of her time—independent, talented, and a pioneer of low-rise, flared (camo) pants."

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"Denim is a style essential for me; it is a fabric that I simply could not live without. The best part about it is how sexy you can make it if you choose to. I prefer my denim to be fun and 'Outrageous,' as Britney once sang. This is one of my fave Brit throwbacks, and it just brings me back to the funk and flair of her dancing days. Back in the day, Britney loved a Versace moment, which is the designer responsible for this all-denim number. The song exudes confidence and ownership of one's sexiness, and I cannot help but be obsessed."

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Next: Every Y2K Jewelry Trend That's Officially Happening Again

How can you not love Britney Spears? She recently posted a video featuring herself in two different cute bikinis along with a lengthy caption about how she approaches wellness. "I run a lot and try to eat clean and be mindful with my food unless I cheat, like last night when I ate a container of peanuts," she wrote in her caption. Relatable. 

While her neon-pink swimsuit is fab, her orange bikini stood out because it hits on one of the biggest trends of summer: cutouts. It's not even May yet, and we've already seen cutouts all over dresses, tops, and, of course, swimsuits, proving that they're going to be a major theme for the next several months. Oh, and don't forget about Zendaya's already-iconic ab-baring dress at this year's Oscars. Scroll down to see Spears's bikini and to shop the cutout trend for yourself. 

Shop the Cutout-Swimsuit Trend

Next, The 4 Types of Swimsuit Cover-Ups Every Fashion Girl Owns

When it comes to awards in the entertainment industry, it’s the Oscars that gets most of the hype. But, any die-hard pop culture fanatic knows that for the past 36 years, the MTV Video Music Awards is the one awards show that cannot be missed. Not only has it delivered some of the best performances of all time (from Britney Spears to Madonna) and been the setting for iconic feuds (ahem, Taylor Swift versus Kanye West), but the fashion of all fashion moments frequently occur on the red carpet and during on-stage performances. While you may be wondering, last year’s 2019 awards show was the last "normal” red carpet we’ll see for a while, the truth is, only time will tell. , But that doesn’t mean we can’t pay homage to several of the most iconic outfits, style icons, and memorable moments that shook us in years past. Put your seatbelts on, because we’re about to travel back in time to see the wildest, raunchiest, and most Avante Garde moments in the history of the MTV Video Music Awards.

1984 MTV Video Music Awards

WHO: Madonna 

WHAT: ’80s wedding dress and "Boy Toy” belt. 

One could say the very marriage of music and fashion at the MTV Video Music Awards began at their inaugural event back in 1984. Courtesy of Madonna, of course. Her performance of "Like a Virgin” in an ’80s wedding dress with a "boy toy” belt kicked off the avant-garde style, and performances that became peak VMA materials and inspired performances and red carpet looks thereafter.

1987 MTV Video Music Awards

WHO: Cher

WHAT: Beaded leotard, long black coat. 

Cher has never been one to shy away from serving an iconic look—after all, who could forget her Met Gala look from 1974? And her ensemble for the ‘87 MTV Video Music Awards was no different.

1989 MTV Video Music Awards

WHO: Christina Applegate, Brad Pitt

WHAT: On Christina: Floral a-line dress and matching scarf. On Brad: Black Blazer, Floral Vest; and a T-Shirt. 

Oh, how could we forget this moment from the 1989 MTV VMAs? I’m still not over this relationship—or these looks for that matter. I mean Pitt’s blazer and floral best situation? Peak ’90s fashion. And Applegate’s a-line floral dress and matching scarf? Too sweet. They may have not lasted, but these looks still have my heart.

1990 MTV Video Music Awards

WHO: Madonna

WHAT: Victorian gown, and fan. 

Let’s be real: Madonna has single-handedly given some of the best MTV Video Music Award show performances. Who could forget her performance of Like a Virgin in an ’80s wedding dress at the inaugural show? Or when she stunned audiences by kissing Britney Spears and Christina Aguilera on stage in 2003? But the look (and performance) that definitely deserves some real estate in your brain is her Victorian-inspired ensemble for her performance of Vogue, at the 1990s show. The fan? Everything. 

1992 MTV Video Music Awards

WHO: Cindy Crawford

WHAT: Versace dress

Before Bella and Gigi Hadid were the best-dressed attendees of the 2019 awards show, there were the supermodels of the ’90s; specifically Cindy Crawford. Who would ever want to forget this leather and sheer Versace dress? Not me, fam, not me.

1995 MTV Video Music Awards

WHO: TLC

WHAT: Matching head-to-toe white looks. 

It’s not a roundup of quintessential MTV VMA looks if we don’t speak to the power of the girl band with matching ensembles. And while getting matchy-matchy on the red carpet was king in the ’90s and early 2000s; no other look is still as relevant as TLC’s 1995 MTV VMAs ensemble. With baggy pants, bare midriff, and chunky boots; this is an influential look we still see popping off on the gram today—and as far as the video they took four nominations home for that year, the song, Waterfalls is still a classic.

1997 MTV Video Music Awards

WHO: Mariah Carey 

WHAT: Bandeau top, and black slit skirt. 

The year is 1997, and the radio is bumping, Mariah Carey’s most recently released album, Butterfly. So it makes sense that she was invited to the MTV Video Music Awards to present LL Cool J with his Video Vanguard award. But really, what makes this moment stick is Carey’s very on-brand, very ’90s sleek two-piece number.

1998 MTV Video Music Awards

WHO Gwen Stefani 

WHAT: Baby blue furry bikini top, futuristic skirt over black pants, and platform sandals. 

For better or for worse, the MTV VMAs have always served up some of the most controversial looks—including, Gwen Stefani’s 1998 look. There are so many things that make this look from Stefani both iconic and questionable; like the futuristic skirt over the pants are so ’90s, but the Bindi Crystals are problematic. No matter your thoughts or feeling about this look, I’m thinking the furry blue bikini top with matching hair may be something we need to bring back.

 1999 MTV Video Music Awards

WHO: Prince

WEAR: Head-to-toe electric blue outfit. 

There are some years of the MTV VMAs that take the word iconic to a whole new level; the 1999 awards show was one of them. Not only did Prince serve up this iconic head-to-toe blue metallic look with hoops and matching braids. But, when the network asked him to perform his song, 1999, he rebuked and agreed to introduce TLC onto the stage. Basically, Prince was always willing to take a risk—which is why his legacy is woven into the fabric of the cultural zeitgeist. 

WHO: Lil Kim

WHAT: Custom purple jumpsuit with matching pasty. 

It’s not a list of icons (or iconic looks for that matter) if the mother of rap, Lil Kim isn’t on it. Not only did she pave the way for some of our favorite female rappers of this generation, but she served one of the most talked-about, most remembered looks probably in the history of the MTV VMA’s back in 1999. Kim’s custom jumpsuit by her stylist, Misa Hylton, not only attracted the attention of Diana Ross, but it ushered in a new wave of all-but-naked red carpet that still has the world-shaking. 

 2000 MTV Video Music Awards

WHO: Jennifer Lopez 

WHAT: Sean John crop top and jeans. 

Jennifer Lopez knows a thing or two about putting together an ensemble that’s bound to go viral—and while there are a plethora of looks that can be recalled, maybe one of her most famous MTV VMA looks is the one she chose to wear to the 2000s award ceremony with her partner at the time, Diddy. She may not wear Sean John anymore—or date him for that matter —but twenty years later, her abs are pretty much the same. 

WHO: Aaliyah

WHAT: Roberto Cavalli gown. 

Before the beloved R&B singer, Aaliyah left us, she shared a few parting gifts. This includes her attendance at the 2000 MTV VMAs where she not only won Best Female Video that year for "Try Again,” but also served an iconic final look in a head-to-toe yellow zebra dress designed by Roberto Cavalli.

WHO: Pink

WHAT: Fur coat, halter top, low-rise denim. 

Singer Pink’s debut appearance at the 2000 VMAs epitomized the 2000s grunge fashion trend. How could anyone forget the usage of that much hair gel? How many pink at-home box-dye kits were bought after this red carpet look? How did her pants stay on despite the fact there’s no waistband? I still have so many questions…

 2001 MTV Video Music Awards

WHO: Britney Spears 

WHAT: That snake, fam. 

Not to play favorites, but we all know that if we’re ranking some of the most iconic MTV Video Music Award performances, no list is complete without the one-and-only Britney Spears. The moment she slithered onto the stage with a python to perform I’m a Slave 4 U, she solidified her spot in the VMA history books. Don’t believe us? Rewatch her performance for yourself.

WHO: Shakira 

WHAT: Feather crop top, leather cowboy chaps. 

While Shakira’s performance with fellow pop star Jennifer Lopez for the 2019 Superbowl may be the only look you can’t get out of your head; I’m here to remind you, she’s always been one to serve a look whenever, and wherever. The proof is what she chose to wear to her MTV VMA debut in 2001—the cowboy pants, leather pants, and feather crop top are only a look that she could pull off.

WHO: Destiny’s Child 

WHAT: Matching coral outfits with turquoise jewelry. 

Ahh, who could forget the head-to-toe coral matching ensembles Beyoncé, Kelly Roland, and Michelle Williams wore to the 2001 MTV Video Music Awards? If you could survive wearing coral in the early 2000s, you can survive anything.

2002 MTV Video Music Awards

WHO: Christina Aguilera

WHAT: Baker boy hat, halter top, mini skirt, knee-high boots. 

Oh, the 2000s really did have some wild red carpet moments; and this 2002 MTV VMA look from Christina Aguilera fits the bill. Don’t get me wrong here—the look is cute and a quintessential VMA look in and of itself, but we all know only Christina Aguilera could pull off both presenting the Best Male Video to Eminem (despite their long-running feud), and this much midriff with the utmost grace. 

2005 MTV Video Music Awards

WHO: Rihanna

WHAT: White low-rise jeans, a crop top, and a bedazzled vest. 

It’s crazy to think that Rihanna was only seventeen when she emerged on the MTV VMA red carpet in 2005 in quintessential mid-2000s look; and since then, has pretty much ruled every red carpet thereafter. As a vested RiRi fan, being able to witness the evolution of Rihanna’s career and style is something I’d replay forever.

2009 MTV Video Music Awards

WHO:  Lady Gaga 

WHAT: Alexander McQueen lace dress. 

No matter the year, no matter the show, Lady Gaga always brings it. Gaga’s beauty moments, personal style, and red carpet looks have always been regarded as show-stopping. After all, who could forget the meat dress she wore to the 2010 MTV VMAs? And while Gaga’s delicatessen-derived dress may be one of the earliest ensembles seared into the collective conscious, it should be known that Gaga was serving up shocking looks well before then Her multiple ensembles for 2009 MTV VMAs (like this full-body, red lace Alexander McQueen dress) are a prime example of Gaga’s ability to create a look rooted in the cultural zeitgeist for years to come.

WHO: Taylor Swift

WHAT: Kaufman Franco gown. 

Possibly one of the most famous moments in awards shows history (and definitely in the history of the MTV VMAs) was when Kanye West interrupted Taylor Swift’s acceptance speech for Best Female Video of 2009. Taylor, of course, handled the situation with grace in a Kaufman Franco gown, performed live after the incident, and even got back her moment later in the show when Beyoncé invited her onstage to finish her acceptance speech. Making this by far one of Swift's most stylish moments. 

2010 MTV Video Music Awards

WHO: Lady Gaga 

WHAT: The meat dress. 

I’ll double down on stating the obvious that Lady Gaga has, and always will bring her a-game to the red carpet. We just have to take another moment to respect the flank steak dress designed by Franc Fernandez—because, when we talk about things forever seared into our minds, it’s this look she wore to the 2010 MTV VMAs. And while we know for a fact this dress has gone down in history as one of the most iconic VMA looks (as the dress is housed at the Rock and Roll Hall of Fame and Museum) the only question I still have is; what exactly she put inside the meat clutch?

2011 MTV Video Music Awards

WHO: Beyoncé 

WHAT: Dolce & Gabbana Purple sequin suit. 

As a member of the Beyhive, I must fully admit that the majority of Beyoncé’s looks and performances are forever ingrained into my mind. I spent copious hours debating whether her leotard look from her performance of Single Ladies (Put a Ring on It) at the 2009 VMAs or the moment she won her video vanguard award in 2014 deserved a spot on this list. But frankly, her perfect performance at the 2011 MTV Video Music Awards is well historic. Not only did she nail every single note in this stunning Dolce & Gabbana sequin suit, but at the end of her performance, she unbuttoned her blazer to reveal she was pregnant with her first child, Blue Carter Ivy—talk about a moment. 

2013 MTV Video Music Awards

WHO: Selena Gomez, Taylor Swift 

WHAT: On Selena: Atelier Versace dress, and Schutz Shoes; On Taylor: Hervé Léger By Max Azria gown. 

The 2013 MTV VMA show was one for the books; at least for former Disney stars like Selena Gomez and Miley Cyrus. While Cyrus’s infamous onstage performance went viral, the attention should have also been on that year’s winner of Best Pop Video, Selena Gomez. Not only did she take away an award for her sexier video, Come & Get It, but previous to the stars more youthful style choices; she wore a Versace gown with a bustier detail and high slit. Basically, 2013 was the year was the stars embraced more risqué looks that would alter the courses of their careers and pop culture itself.

2014 MTV Video Music Awards

WHO: Katy Perry

WHAT: Atelier Versace. 

We’re not the only ones who live for a Britney Spears red carpet moment. In an homage to Spears and Justin Timberlake’s red carpet look for the American Music Awards in 2001, Katy Perry wore this head-to-toe denim Atelier Versace gown to the 2014 MTV Video Music Awards, giving the look a reboot in pop culture’s collective memory. If you’ve ever wondered how to wear head-to-toe denim, this is how you do it. 

2015 MTV Video Music Awards

WHO: Nicki Minaj

WHAT: Labourjoisie gown. 

Nicki Minaj has her fair share of iconic style moments—but what makes her stunning 2015 MTV VMA head-to-toe gold look so much different is the birth of the phrase, "What’s good, Miley?”. If we were to take a time machine back to 2015, Minaj’s Anaconda was nominated (and won) Best Hip Hop Video. When Minaj voiced her frustration around the lack of body diversity in other categories like Video of the Year, fellow artist Miley Cyrus commented back in the press leading to Minaj’s iconic call-out on-stage the MTV VMA stage. While we may all remember her speech, the moment should also be remembered for what it truly was; a call to celebrate the beauty of all bodies, especially if they’re in a Labourjoisie gown.

WHO: Miley Cyrus

WHAT: Atelier Versace.

When it comes to throwing a curveball (or a wrecking one) we thought we saw it all after Miley Cyrus’s controversial 2013 MTV VMA performance with Robin Thick and a foam finger; but alas, she wouldn’t stop serving looks. With eleven outfit changes in total, all styled by Simone Harouche, the 2015 show host, made sure her silver suspenders, basically naked, and seriously outrageous style was center stage.

2016 MTV Video Music Awards

WHO: Beyoncé, Blue Ivy

WHAT: On Beyoncé: Francesco Scognamiglio dress and Lorraine Schwartz jewelry. On Blue Ivy Carter: Lorraine Schwartz tiara; Mischka Aoki Grand Royalle Dress; Giuseppe Zanotti Dolly Sneakers. 

The thing I love about the MTV Video Music Awards is that you get to see a lot of full-circle moments; from the artist’s first red carpet moment to winning their own vanguard. But one full-circle MTV VMA moment that’s forever seared in my mind, is when Beyoncé brought her daughter, Blue Ivy Carter, in her little $11,000 dress to the 2016 award ceremony. For Beyoncé to announce her pregnancy on stage back in 2011, and then bring Blue in the downright chicest ‘Lil number a few years later had many beehive members (myself included) clapping and crying over this momentous occasion.

WHO: Rihanna

WHAT: Alexandre Vauthier haute couture collared gown with a grommet belt. 

It’s not a VMA show unless the relationships, both professional and romantic, are on display. For many fans, the confirmation of Rihanna and Drake’s relationship rumors met their end at the 2016 MTV Video Music Awards. Although the moment that Rihanna dodged Drake’s PDA after her acceptance of the Vanguard award went viral, the real attention grabber of the night should have been this haute couture look. 

2018 MTV Video Music Awards

WHO: Cardi B

WHAT: Nicolas Jebran dress; Lorraine Schwartz jewelry; Alexander Acosta shoes.

2018’s MTV VMAs was a moment to remember for Cardi B for various reasons; it was the artist’s first red-carpet post-pregnancy, and she came through drippin’ in a velvety Nicolas Jebran dress. Not only did the artist further prove she’s a major style icon, but she also made history when she won the awards for song of the summer and best new artist.

2019 MTV Video Music Awards

WHO: Lizzo, Lil Nas X

WHAT: On Lizzo: Marc Jacobs Prom Dress, and scünci hair accessory. On Lil Nas X: embroidered suit by Union Western Clothing, and Gladys Tamez hat. 

2019’s MTV VMAs were filled with so many good looks, but if we’re being honest, only two stars stole the spotlight with their performances. As some of the best new-comers to the music industry, Lizzo and Lil Nas X brought their A-games with sequins, ruffles, and bedazzled things galore. Their looks are the types we always look forward to every VMA: a little outlandish, a little sparkly, and something to remember for years to come.

Next: 15 Photos That Prove the VMAs Were Wild in the ’00s

Let’s be honest: It’s nearly impossible to have a discussion about the early ‘00s without so much as a mention of Britney Spears. After all, with a handful of number-one songs, best-selling albums, and a movie under her belt, there couldn’t be a better representation of the era. And as one of the biggest stars of the early aughts, Britney Spears’s outfits were just as iconic as the woman who wore them.

To say that Britney Spears has had memorable fashion moments would be major understatement. From music video ensembles that launched a lifetime of inspiration for costumes everywhere to Y2K trends like ultra-low-rise jeans and Juicy Couture tracksuits—and don’t get started on that VMAs performance look (you know the one)—it’s clear that throughout the years, the singer has become a cultural icon.

Just in case you need a refresher on her most notable sartorial moments, we’ve gathered them all right here. Scroll down to see them all.

Kicking off this roundup of Spears’s most iconic looks is this ensemble from her "…Baby One More Time" music video, which will always be one of her most memorable looks—pom-pom hair ties and all.

The early aughts was also a time where Juicy Couture tracksuits reigned supreme. Here, she complements the look with layered necklaces and tinted sunglasses.

If you're asking us, no couple has made as big of a splash on the red carpet as when Spears and Justin Timberlake coordinated in head-to-toe denim ensembles.

To attend the Grammy Awards, Spears took a minimal approach with a white streamlined gown and a fur shawl.

It goes without saying that Spears’s performance ensembles, like this bedazzled matching set, were next-level. 

Of course, nothing can top this ensemble, which goes down in history as one of the most iconic VMAs perfomance outfits to date.

In her earlier days of performance, the young singer opted for classic Y2K trends like cargo pants and tube tops.

Early in her career, the singer opted for more understated ensembles, including this T-shirt and denim skirt combination.

Britney Spears also mastered the art of the ultra-ultra-low-rise jeans. Paired with a rhinestone belt and a lingerie-inspired bustier, this ensemble showcases the height of the early '00s.

Ah, the '90s. An era defined by MTV, Lisa Frank, and more boy bands than we care to count. (For the record, I think 98 Degrees was underrated.) Some of my absolute favorite pop culture moments were born in this decade, and when I think back on it, I can't help but relish in the wonderfully wild '90s hairstyles.

From messy buns to chic claw clips to a broad selection of bangs, there was something special about the hair trends from this time. It girls of the era, such as Britney Spears, Janet Jackson, and Gwen Stefani, served up enough inspiration to carry us right into the following decade. "There was a big divide between clean, layered glam and edgy, rebellious looks," says Giles Robinson, celebrity hairstylist for Color Wow. "It was the decade where hair was part of your identity, expressive, individual, and tied to music, fashion, and film."

If you're as nostalgic as I am, then you'll love this roundup of the 20 most quintessentially '90s hairstyles we would low-key wear today. I might get some strange looks, but I'll never shy away from an adventurous beauty look. Keep reading for our favorites.

1. The Twist-Back

The only thing that could make this style more '90s is a butterfly clip placed at the end of the twisted section. This half-rolled hairstyle, also dubbed "picture-day hair" by the elementary school set, ruled the decade.

2. The Winona Pixie

The subtle layers and laid-back styling made this pixie cut an instant hit when Winona Ryder debuted it in the late '90s. "In the ‘90s, styles were often a bit more literal, chunkier highlights, spikier updos, harsher partings," says Robinson. "These days, we’re revisiting the same trends but softening them."

3. Micro Braids

No one rocked micro braids quite like Brandy. This was her signature hairstyle on her hit TV show Moesha as well as in her real life. Plus, the length of this look perfectly frames her face.

4. Bumped Bob

The soft curl added to this classic bob adds an interesting element to the hairstyle. Shown here on an angelic-looking Angelina Jolie, this spin on the bob would make us do a double take if we saw it walking down the street today.

5. Mall Bangs

There was a period of time when it seemed like every TV character was sporting these voluminous, feathered bangs. From D.J. Tanner to Kelly Bundy and, of course, Tiffani Thiessen's Saved by the Bell character, Kelly Kapowski, these bangs were the mark of a cool girl.

6. Claw Bangs

On the other end of the bang spectrum were these fringe bangs, defined by face-framing, peekaboo pieces.

7. Teeny Double Dutch Pigtails

This easy hairstyle screams the '90s. Britney Spears fashioned her short hair into two messy plaits fastened on the ends with elastics and just enough hair peeking out of the bottoms for a playful 'do.

8. The Flip

From the pencil-thin eyebrows to the dark-red lipstick and the leopard-print collar, this photo of our queen Drew Barrymore is like a time capsule into the '90s. Her flipped hair (and those enamel hair clips) is another huge clue as to which decade we're looking at.

9. Bedazzled Bandanas

Okay, so in all fairness, this photo was taken in the year 2000. But it's important to call out here because it exemplifies the influence that '90s hip-hop had on style and culture well into the decade that followed. J.Lo's bedazzled bandana accentuating her braided hairstyle.

10. Jumbo Box Braids

Janet Jackson's braids circa Poetic Justice were (and still are) a legendary look. The addition of this newsboy cap and bold red lip solidifies it as one of our favorite looks of hers.

11. Butterfly Clips

Gwen Stefani wasn't afraid to push the envelope when it came to hair. But here, we see her adopting a trend that took hold of just about every '90s girl: the infamous butterfly clip. It was such a thing.

12. Shortest-Possible Platinum Pixie

Jada Pinkett Smith showed us plenty of short haircuts in the '90s, but this bleach-blonde, barely there cut takes the cake.

13. The Hilary Banks

Everything about The Fresh Prince of Bel-Air is a perfect representation of '90s life, but nothing compares to Hilary Banks's perfectly coiled coif, which she'd often top with a statement hat or oversize bow to tie her ensemble together.

14. Messy Bun + Wispy Tendrils 

Don't be fooled by the name: The messy bun could be a super-chic look. Paltrow proved this point on a '90s red carpet, where she kept with the undone theme by letting some face-framing curls hang loose.

15. The Rachel

Do we even need to explain? The power friends and Rachel's character truly sparked a movement for short bobs. "The '90s were all about statement hair, from polished supermodel blowouts to grungy, undone texture," says Robinson. "You had the 'Rachel' cut dominating salon requests alongside sleek high ponytails, butterfly clips, and ultra-straight strands thanks to the rise of flat irons."

16. The Sky-High Pony

Leave it to supermodel Tyra Banks to claim even more height with this sleek high pony. The flipped curl and swooshed bang add that much more '90s flair.

17. Antennae

Nineties girls like Jennifer Love Hewitt were all about an undone look, as evidenced by the trend of leaving just two straight strands of hair out in the front of an otherwise polished style.

18. Two Braids

In an era marked by plenty of grungier styles, this almost childlike style really stood out. Note the clipped bangs as well.

19. Chunky Highlights

Apparently subtlety just wasn't in style in the '90s. Kelly Rowland's lurid streaks, coupled with her choppy cut, were clearly meant to stand out. "Music videos and red carpet appearances influenced styles massively, from Destiny’s Child's sleek looks to TLC’s playful textures," says Robinson. "These hairstyles worked because they had personality. They were bold, fun, and easy to replicate at home with a bit of gel, mousse, or a heat tool."

20. Scrunchies

Scrunchie madness was such a defining trend of the '90s. They were perfect for securing any kind of ponytail or even just wearing around one's wrist like a bracelet. You know, just in case.

This article was originally published at an earlier date and has since been updated.

Yesterday, we covered Scarlett Johansson's jaw-dropping engagement ring reveal, and now a new day has brought us a fresh celeb ring debut. On Monday night, Spears attended the A-list premiere of Once Upon a Time in Hollywood, which also boasted the movie's stars Brad Pitt, Leonardo DiCaprio, and Margot Robbie. The event marked her first red carpet event with boyfriend Sam Asghari—but he may actually now be her fiancé.

Spears walked the high-profile red carpet with a glittering new diamond ring on her left hand. The ring boasts three round-cut diamonds and a simple gold band, which popped against the bright-red color of her dress. To gain more insight, we tapped Kathryn Money, the VP of strategy and merchandising for Brilliant Earth. Based on her expert knowledge, Money estimates the ring to be worth $70,000 to $115,000. She also believes the ring boasts a 2.5-3 carat diamond in the center, flanked by two 1.5-carat diamonds on either side. 

Spears has not confirmed the engagement yet, but stay tuned as we learn more. Scroll down to see Britney Spears and Sam Asghari on the red carpet, and get a close-up look at her diamond ring. 

Shop Three-Stone Rings

Next, the nine best affordable celebrity dresses of summer 2019.

If you ask us, no one was a more iconic representation of early '00s fashion than Britney Spears. Longtime fans of the pop star will remember how classic the fashion was in 2002's Crossroads, and don't even get us started on her epic VMAs performance outfits through the years. There's no doubt that Spears's style will go down in fashion history books for the era, and she's certainly solidified her love for all things naughties fashion… even in 2018.

While out and about in Paris recently, Britney wore one of the most controversial denim trend of the early aughts: low-rise jeans. Not just any below-the-belly-button denim, either, but a pair of ultra-, ultra-low-rise jeans we honestly haven't seen in years. For a while now, high-rise styles have dominated the fashion scene, leaving anything lower than waist-pinching in the dust. Maybe the singer's onto something, though. After all, we have been seeing more and more '00s trends—logo bags, tiny-strap sandals—creeping back into style.

No matter how you feel about the denim trend, you have to hand it to Spears for refusing to relinquish her low-rise jeans just because they're not what everyone else is wearing at the moment. Below, see how she styled them with knee-high boots and a romantic off-the-shoulder top.

On Britney Spears: H&M Off-the-Shoulder Blouse ($25)

Shop low-rise jeans:

Now read our exclusive interview with Serena Williams.

I'm not sure if most film critics would share my enthusiasm for Britney Spears’s 2002 road trip film, Crossroads. But I’m no film critic, so let me be clear: It’s a classic. You’ve got a pre-Avatar-fame Zoe Saldana, eventual Litchfield inmate Taryn Manning, and the biggest pop star of the ’00s taking a post–high school graduation road trip. And while I won’t give too much away about the teen flick, there’s a Spears rendition of “I Love Rock ’n’ Roll” that’s iconic (in some circles, I’m assuming). What’s more? The movie is chock-full of nods to 2018 trends.

Of course I didn’t know it at the time but Lucy, Kit, and Mimi (Spears’s, Saldana’s, and Manning’s characters, respectively) were not only sources of inspiration for our closets then but also serve as inspiration to 2018’s obsession with bucket hats, low-rise jeans, going-out tops, and more.

Ahead, I’m breaking down a mere sampling of the styles that make me so nostalgic for the ’00s, as well as shopping ones that prove it wasn’t all that long ago.

I’m calling this trend the prom-dress top. Yes, they are wearing their prom dresses in the opening scene of the movie, but this aesthetic—square-neck silhouettes, spaghetti straps, and fabric with lots of shine—has been popular recently, too. The look is as if you’ve chopped off the bottom half of your prom dress (brands like For Good Luck do exactly that) and then styled it with something less formal.

Yes, bucket hats have made a welcome return in 2018. And if you’re matching it exactly to your henley, more power to you.

For me, the fashion in this photo is all about Saldana’s adorable tube top. And with the return of the strapless look in 2018, her head-to-toe ensemble doesn’t seem dated at all.

I’ve already waxed poetic about the appeal of a cardigan, but before I ever put too much thought into it, Spears wore the trend in Crossroads. Considering her somewhat more daring outfits in the film, this one was meant to keep things obviously sweet as Lucy visits her estranged mother. (Hi, Kim Cattrall!)

Wow, where do I begin? The low-rise jeans, the chain belts, the feathers? There are 2018 micro-trends riddled in these looks. But Saldana’s very ’00s top feels similar to other versions I’ve seen lately—more so in its scarf-life silhouettes, not so much animal graphics.

Up next: Here’s what Cher Horowitz’s closet would look like in 2018.

Last night, I.AM.GIA presented its debut show at Fashion Week Australia. Having launched only a year ago, the brand has quickly become a celebrity favourite, known for its edgy and out there designs—and the latest collection definitely played up the bad girl-vibe. While the runway show was undeniably more risqué than other collections we’ve seen thus far, we can't say we were completely shocked. After all, it’s the brand’s wild aesthetic that helped it rise to fame in the first place.

While it may be difficult for most of us to imagine wearing the collection in real life, there is one person we can distinctly envision in it: Britney Spears circa 2000. A denim coordinated ensemble gave us flashbacks to Britney’s iconic red carpet moment with Justin Timberlake… and those pleated mini skirts? Straight out of the “Baby One More Time” music video. In fact, one of the looks even had us doing double takes: There’s no denying that that the two-piece leather coordinate is reminiscent of Brit’s 1999 MTV Video Music Awards getup. If you need more proof, keep scrolling to see the pieces from the I.AM.GIA show that we think 2000's Britney would’ve loved.

It's almost like this outfit was made for 2000's Britney.

"I must confess, I still believe." 

A closer look at the aforementioned leather outfit.

2000s Britney loved all things strappy.

Someone find Justin Timberlake ASAP.

Convinced yet? Check out some of the other new designers at Fashion Week Australia this year.

Related: Every Story We Have on Fashion Week Australia

Kenzo is giving us what we never knew we needed: Britney Spears wearing a denim baseball hat, denim underwear, and thigh-high denim boots. The singer stars in the brand's newest campaign, and the photos, shot by Peter Lindbergh, are instantly legendary.

"La Collection Memento N°2 focuses heavily on denim and was inspired by the 1986 Paris runway debut of Kenzo Jeans," Kenzo explained in a press release. "But a more esoteric theme is 'Icons.' The Kenzo motifs (the tiger, The Great Wave of Kanagawa) are all featured heavily, as well as (for the advertising) Britney Spears."

Kenzo went on to explain how its star fits in perfectly with the brand. "Britney Spears. KENZO. Peter Lindbergh. What could at first seem an unusual trifecta, actually makes total sense when one learns that the collection is all about icons," the press release reads. "Britney is certainly an icon and the quintessential queen of denim. Of similar stature in the photo world is Peter Lindbergh, whose British Vogue cover of Linda, Naomi, Cindy, Tatiana and Christy ignited the age of the supermodel."

Read on to see the epic new campaign.

What happens when Britney Spears and Ellen DeGeneres take over a mall? Hilarity ensues, of course. The talk-show host took the singer to a local mall in Los Angeles, where the duo caused quite the ruckus. From boxing in high heels and stealing a purse to eating ice cream at Pottery Barn and joking with customers, Spears and DeGeneres hilariously wreaked havoc on innocent shoppers.

Although everyone loves Britney Spears for her music, she's been showing off her comedy chops recently. First, we were obsessed with her Carpool Karaoke segment on The Late Late Show With James Corden, and now this Ellen clip is equally gut-busting. We can't wait to see what else she has up her sleeve—but whatever she does next, it's safe to say we'll be watching!

Hit play to watch Britney Spears's hilarious segment on The Ellen DeGeneres Show!

What was your favorite part of the clip? Tell us in the comments below, and then shop black ankle boots like Spears wears in the video!

Opening Image: Getty Images

The Late Late Show with James Corden's wildly popular Carpool Karaoke segment has lured the likes of Selena Gomez, Adele, and Michelle Obama to his passenger seat. Britney Spears, the latest to join the growing list of superstars to take part in the fun, belted out her hits "...Baby One More Time", "Toxic", and "Oops! ...I Did It Again" with Corden. For the grand finale, Spears ditched her very 2016 off-the-shoulder top for a very 1998 schoolgirl look similar to what she wore in the video for her debut single. (It's worth noting that Corden also opted to twin with Spears in a schoolgirl costume.)

The iconic, infamous costume is one of the best examples of how significant of a role fashion plays in the world of music. When you hear "...Baby One More Time", it's nearly impossible not to picture Spears dancing in her school uniform, almost two decades after it took the world by storm. Spears's participation in Carpool Karaoke was perfectly timed with the release of her new album Glory, which is available as of last night. 

Watch Britney Spears's Carpool Karaoke in full below and shop schoolgirl–inspired pieces (in the spirit of nostalgia)! 

Shop Britney's Look:

What's your favorite Britney Spears video costume? Tell us in the comments!

Opening image: CBS

Britney Spears, “Toxic,” and Carpool Karaoke are coming together for a match made in heaven, as far as we’re concerned. Joining The Late Late Show host James Corden on his super-popular segment, Spears will appear on the show tomorrow night, but we already have a sneak peek at the sure-to-be-epic video. We’re officially counting down the hours until the full episode airs.

Though the segment has included some of the biggest names out there, including Michelle Obama and Selena Gomez, for starters, there’s something about a good Britney Spears–circa-2003 throwback that really gets us giddy. From her outfit in the clip, it’s clear that Spears has been paying attention to major summer trends: She’s wearing an off-the-shoulder top with an of-the-moment black choker, along with oversize sunnies and basic black jeans. We apologize in advance for getting “Toxic” stuck in your head all day.

Scroll down to get a sneak peek at Britney Spears’s Carpool Karaoke segment with James Corden, airing tomorrow!

Will you be tuning in for her segment tomorrow? Tell us in the comments below, and then shop black chokers like she wears in the video!

Opening Image: Getty Images