Looking back, the '90s and the decade's trends feel like a golden era—the Game Boy! The Spice Girls! The Parent Trap! The last cell phone-less generation!—most of all regarding '90s fashion. Scrunchies, acid-wash jeans, tube tops, capri pants, and jelly sandals reigned supreme among '90s style trends, along with crimped hair, Mary-Kate and Ashley Olsen (who brought back the jelly sandal with their brand The Row), and punk rock. It was a glorious time, made only more glorious by the A-listers and '90s supermodels who blithely wore their finest on the red carpet and out and about, secure in the knowledge that they would never have to look back on these iconic looks and feel anything other than pride.
Unfortunately, in 2024, some of these '90s looks...hit a little differently. On the other hand, these looks prove just how much the '90s influenced some of today's most in-demand trends—and right onto the fall 2024 runway. So sit back, grab a packet of Pop Rocks, and instead of wondering how 1990 can be as far away from the present day as 2050 (!), enjoy these looks, which represent the very best (if "best" is the right word) of polarizing '90s fashion.
It doesn't get more iconic than Pamela Anderson in this pink fuzzy hat an white buster combo at the 1999 MTV Video Music Awards. The blue eyeshadow really completes the look.
This is the slip dress to end all slip dresses. Actress Jodie Foster donned this classic, elegant pick at the 1997 Vanity Fair Oscar Party, proving that simple sometimes is better.
Another stunner in red is Brooke Shields in this cherry-hued column gown at the Golden Globe Awards in 1998. The fresh-faced model added a red lipstick that perfectly coordinates with the look.
Naomi Campbell looks stunning in just about everything she wears, but this pastel yellow boat-necked number that she wore to the The 68th Annual Academy Awards in 1996 is one of my underrated favorites.
This leather blazer look that Lauryn Hill wore at the The 1999 Source Hip-Hop Music Awards is totally copy-able now thanks to the never-ending trend cycle.
Meg Ryan in this coat the "Anastasia" New York City premiere in 1997! That's it, that's the whole caption.
This simple cheer maxi dress on Liv Tyler in 1995 is the epitome of '90s fashion.
Digital Lavender isn't just trending now. It was also big in the '90s, as proven by supermodel Christy Turlington on the runway at Versace in 1994.
The velvet suit that spawned a million Pinterest pins! Gwenyth Paltrow wore this now-iconic velvet suit to the 1996 MTV Video Music Awards in New York City and became one of the most clicked-on images ever since.
Winona Forever! This simple tank-and-trousers 'fit on the red carpet for the 1998 MTV Video Music Award Arrivals is so simple, so easy, and so cool.
Who doesn't love a simple slip dress! Catherine Zeta-Jones looks bubbly and oh-so-'90s at the 1999 MTV Movie Awards.
One of the best—and most stylish—TV characters of all time, Hilary Banks from 'The Fresh Prince of Bel-Air' (aka Karyn Parsons) is always on my style board.
In a now-iconic clip from the Todd Oldham fashion show in 1994, Shalom Harlow overtakes fellow supermodel Amber Valletta on the runway in this micro mini skirt. Who would have guessed that looks inspired by this one would pop up on the runways and in street style photos just shy of 30 years later?
Kelly Ripa's slinky white pearl-encrusted gown at the 5th Annual Daytime Emmy Award in 1998 is currently on my wedding mood board. The slicked-back hair adds just a touch of edge.
Confirmed: the sheer trend started in the '90s, and on Brittany Murphy specifically. This grungy ensemble from 1999 would totally work today.
Cameron Diaz was the queen of easy, laidback style in the '90s. Case in point, this effortless two-piece set at the The 70th Annual Academy Awards in 1998.
Another day, another reason to wax poetic about Winona Ryder's '90s style. This beaded halter from 1998 is sexier than some of her other, more popular looks from the decade, but it's still one of my favorites.
There's nothing better than Kate Hudson in pastel dress. Need I remind you about the epic yellow gown from 'How to Lose a Guy in 10 Days?' This icy blue pick that she wore to the Los Angeles premiere of '200 Cigarettes' is too good not to talk about.
Dressed in head-to-toe black leather, Destiny's Child proved that they were the moment on the red carpet at the MTV Europe Music Awards in Milan, Italy in 1998.
If you love pink, wear it from head-to-toe. This Lil Kim look proves that monochromatic dressing is always a good idea, even down the wig.
She can do sporty looks too, people! Pam Anderson took a cooler, more casual approach to her style at in 1994.
Grace Jones can do no wrong. This blue bustier moment from 1992 undoubtedly inspired a similar Tom Ford look that Zendaya later wore in 2020.
Always cool and never too styled, Aaliyah made black and white look chic in 1995.
Queen of casual ensembles, Meg Ryan wore this oversized blazer, fitted trousers, and brogues is the ideal combination of menswear-meets-womenswear.
The iconic high-low moment when Sharon Stone wore a Gap button-down with a Vera Wang skirt is forever engraved in my brain.
No thoughts, just this picture of Keanu Reeves in a tan suit at the 1993 MTV Movie Awards.
Supermodel Tyra Banks channeled some serious '20s glamour at the Ziegfeld Theater in New York City.
Jennifer Aniston opted for a grey two-piece at VH1 Divas Live back in 1998, and we would totally wear this look today.
Only Iman could get away with wearing this colorful Versace frock to the opening of Chanel's new Flagship Boutique back in 1996.
Does it get more '90s than J.Lo in this slinky chainmail top and a pair of low-rise leather trousers at the MTV Movie Awards? No, it does not.
Claudia Schiffer had the honor of going as the bride at Chanel's Fall/Winter 1993/1994 haute couture collection.
The '90s were clearly a great time for cream-colored suits.
I could totally see one of today's It-Girls donning this satin number that Carla Bruni wore to the Versace High Fashion Show in January, 1995.
The pastel looks on this duo at the 1996 MTV Movie Awards lives rent-free in my mind.
This all-over pink look that Carmen Electra wore to the 1997 MTV Rock 'n Jock Basketball game is pure '90s perfection.
How chic is Elle MacPherson in this micro mini skirt at the 1994 MTV Movie Awards?
Eve donned this glittery micro-mini dress for the Fifth Annual Soul Train Lady of Soul Awards on 1999, proving *just* how influential the '90s were on today's biggest fashion trends.
Kate Hudson looks ever bit the '90s superstar in this sheer corset top and low-rise maxi skirt from1999.
Opera-length gloves may be trending right now, but this pair on Sharon Stone from 1993 proves that they were *always* a good idea.
Never not thinking about this Janet Jackson performance look from 1995.
Yes, this photo is a BTS shot from Sex And The City. Yes, Sarah Jessica Parker still looks amazing.
TLC were ahead of their time in these lace-up coordinating looks at the 1995 MTV Video Music Awards.
This Selena look is forever iconic.
Another day, another oversized pantsuit that I can't get out of my head.
Aaliyah's performance looks were second-to-none.
This leather corseted look on Whitney Houston is what two-piece dreams are made of.
Minutes after this photo was taken, Jolie jumped in the pool at the 1999 Golden Globes. She took home the trophy for Best Actress in a Mini Series thanks to her peformance in Gia.
No one did twinning better than these two. The Olsen sisters matched in black cardigans and fringe skirts at the movie premiere of Anna and the King in 1999.
The singer attended the 1997 Cable ACE Awards and proved then and now that the slip dress is a classic piece to have in your wardrobe. Try styling it with a velvet cape.
The only thing more memorable than Aniston's Rachel Green haircut/outfits was who she was dating at the time: Brad Pitt. We'll just leave this here.
The actress hit all the '90s fashion benchmarks in this outfit: the purple bandanna, the see-through matching purple shirt, a skinny chain belt, and slightly flared jeans.
The singer went for a head-to-toe gold look. Personally, we're getting Academy Award statue vibes.
The star and Janet Jackson dressed up in blazers to attend the 66th Academy Awards Nominees Luncheon in 1994. Bassett went with a bold fuchsia color while Jackson kept it classic in all white.
The supermodel attended the Second Annual Revlon's Unforgettable Women Contest in 1990 at the MET in New York City. She wore a striking halter neck red dress nude tights and red heels. We're eyeing the sparkly diamonds on her neck and ears too.
Who grew up watching Sabrina the Teenage Witch? Here's the actress, circa 1990, in a genie-like costume, complete with a long braid.
The star was a fan of rocking two pieces on the red carpet. She wore this flashy pink fringe outfit to the MTV Movie Awards in 1990.
Also in 1990, Jada Pinkett Smith debuted this shimmery green skirt and top set. We're getting mermaid vibes.
We love a '90s matching moment. Here, Brittany Daniel, Shane McDermott, and Sarah Michelle Gellar coordinated outfits in a promotion for Swans Crossing in 1992.
It seemed like everyone owned a lace slip dress back in the '90s. Here, Blair wore one at the premiere of Cruel Intentions in 1999.
The actress played one of the most stylish moms on TV in The Parent Trap and her fashion sense IRL was equally as good, as this blazer skirt (dress?) set proves.
The actress and singer showed off a matching graphic set in 1990. We're taking bets on what the print is.
The '90s supermodel's crop blazer top and high-waisted pants is a look we still love today.
The singer was known for adding a little glamour to her punk rock looks in the '90s. Here, Stefani arrived to the 1998 MTV Video Music Awards in a fuzzy blue bikini top that matched her icy blue hair and...face jewels.
Always known for pushing the fashion envelope with her style, at 1999 MTV Video Music Awards, Lil' Kim hit the red carpet in an unforgettable boob-baring one-shoulder jumpsuit. The rapper finished off the look with a purple wig.
This model duo owned the '90s with their fashion. Moss and Campbell were spotted leaving a London Fashion Week event hand-in-hand in 1991, wearing their own renditions of school-girl-chic attire.
Aaliyah mastered streetwear long before the term became a fashion phenomenon, as evidenced by her Tommy Hilfiger yellow tracksuit in 1997. The singer was the poster child for the modern-day phrase "chill but still a big deal."
Proof Dontalla Versace and J.Lo go way back. The two posed for the cameras while wearing some glitzy '90s fashion looks of sparkles and metallics.
The model casually out and about while rocking Versace. Iconic! We're getting Cher vibes, except Turlington's sheer top makes the outfit slightly more risqué than Alicia Silverstone's.
This laidback but classic '90s look by the singer and actor can easily be recreated present day. The Poetic Justice star tucked a long-sleeved boatneck tee into a belted pair of mom jeans and wore a newsboy cap over her long box braids.
In 1996, Mary J. Blige attended the Grammy Awards wearing a full leopard print ensemble with velvet gloves and dark sunglasses. It's safe to say this print will never go out of style. What a lewk.
Name a better duo than this King and Queen of Pop. In 1991, Madonna and Michael Jackson arrived to the 63rd Annual Academy Awards in the most glamorous Hollywood outfits. Madonna wore a glittery strapless gown, a fur stole, and Harry Winston jewelry while Michael went for a sequin cream blazer paired with his iconic gloves.
That time Julia Roberts stunned in a suit and tie at the 1990 Golden Globe Awards. The actress had stunned in a variety of dresses in Pretty Woman (released in 1990!) but we love her in this oversize masculine suit just as much.
It's hard to miss the singer's toned abs in this glittery two-piece ensemble in 1990. In fact, this classic-yet-sexy attire has been reworked over the years and celebrities are still loving two-piece skin-baring looks (exhibits A and B).
Singer Mariah Carey stole the show at the 1997 MTV Video Music Awards by baring her abs in a bandeau top and showing off her legs in a high-slit skirt. Mimi's glamorous bombshell style has continued to serve as style inspo for decades to come.
If you've never seen The Nanny, I don't know you. Fran Drescher's outfits on the show, which included teeny-tiny sweaters and body-hugging miniskirts, were iconic looks. Drescher's real life style was a little more toned-down glamorous, like this white halter-neck dress though she did find ways to jazz things up (see: her floral head piece).
If we were to name a more iconic duo than Mary-Kate and Ashley Olsen that would be Tia and Tamera Mowry. The twins were the stars of Sister, Sister and their closets (both on the show and off) were amazingly good. Think everything from covetable denim overalls and bucket hats to these mini shift dresses with the scarves (!!). Someone bring back these exact looks on the runway, please.
Let this photo of Lisa Bonet in the '90s be proof that her daughter Zoë Kravitz is the spitting image of her. In addition to being a sought-after actress during that time, Bonet was known for her free-spirited, bohemian style. Her outfits, like the one on the left, were an expression of her artistic perspective.
The two took couple matching to the next level when they were spotted in Los Angeles wearing white button-down shirts and jeans.
With her unique flower-child-meets-wild-child look, Barrymore was one of the decade's most badass style stars. She borrowed elements of grunge—dark makeup, choppy hair, tattoos—and mixed them with bohemian staples like daisy chains for a style that was all her own. Here she is rocking a fanny pack covered in the word "fuck," because why not.
Before her A Walk to Remember Days, Mandy Moore was an established singer (remember "Candy"?) and definitely a '90s gal. Her style was defined by simple tank tops and bottoms with a thin chain belt running across. This photo is peak '90s.
Madonna is a fashion icon for the ages, but one of her most memorable (and most copied) signature looks was the cone bra that Jean Paul Gaultier designed for her Blond Ambition Tour in 1990.
Before Clueless took the '90s fashion world by storm, introducing Cher Horowitz–plaid and an obsession with Alaïa, Alicia Silverstone's personal style could best be described as laid-back. The actress wore a pair of t-strap Mary Janes with a long skirt and slouchy sweater (because comfort is key, folks).
Since her breakout role in the controversial cult film Kids, Chloë Sevigny has been a "cool girl" beyond typical grunge queens and bubblegum pop girls. Known for her obsession with vintage and her playful take on fashion (she's considered one of the first true street style stars), she became the ingenue every designer wanted as their date at awards shows.
Ryder was the ultimate '90s It girl. In the early part of the decade, she scored a number of roles in cult-classic films, including Edward Scissorhands and Reality Bites, and her tomboyish style quickly caught the public's attention. Raven-colored hair and all-black red-carpet ensembles became her signatures.
Yes, Ryder was a style star on her own. But there's a reason the fashion world is still obsessed with Winona and Johnny's relationship today—the duo were the definition of gothic chic. The couple arrived hand-in-hand at the 48th Annual Golden Globe Awards in 1991 looking like they came straight from the set of a Tim Burton film.
The king and queen of Seattle grunge, Kurt and Courtney were more or less the most influential couple of 1990s fashion. The Nirvana singer arguably started the entire grunge trend, with his mismatched, oversized outfits and shaggy mop of hair. Similarly, the Hole frontwoman was known for her torn, sheer slips, dark makeup, and babydoll dresses.
Liv Tyler was the ultimate '90s babe—who could forget her role, alongside Alicia Silverstone, in the '93 video for Aerosmith's "Crazy?" In 1992, Tyler's wardrobe was filled-t0-the-brim with edgy dresses (like this one) and long skirts.
Princess Di wore this daring LBD the same night Prince Charles' tell-all interview about their life came out. It was dubbed the "revenge dress" because the princess didn't let anyone, or anything, hold her down from shining that night. The off-the-shoulder design and asymmetrical hemline made a major style statement and is one of the most iconic looks of British royalty to date.
The couple arrived to the post-premiere party of Grant's film, Four Weddings and a Funeral in London. Hurley left her style mark that night in this iconic Versace pin dress. Since then many celebrities have tried this look, including Irina Shayk at the 2018 Cannes Film Festival.
Another iconic look from Princess Di. (Hailey Bieber even recreated this casual outfit for British Vogue). She was ahead of her time in adopting the biker shorts and oversized pullover trend, which has just now taken over the fashion world.
Dawson's Creek fans will love this throwback moment from its two cast members at the 47th Annual Emmy Awards. Van Der Beek looked dapper in a suit while Holmes rocked that square neckline gown (that style is now back in fashion) with a ball-shaped floral bag (also back in fashion).
Two words: Carrie Bradshaw. We can't even begin to count how many trends Sarah Jessica Parker's character singlehandedly started in the late '90s, but many of the world's most well-known fashion brands (we're looking at you, Manolo Blahnik) owe her quite a bit of thanks. Here, three years before the premiere of Sex and the City, Parker preluded Bradshaw with this pink, feathery ensemble.
It's impossible to conjure an image of the '90s without picturing the cast of Friends (and, in particular, Jennifer Aniston's now-famous Rachel haircut). In 1995, co-stars Aniston and Matthew Perry walked the 47th Annual Primetime Emmy Awards red carpet in ensembles that defined the decade: Aniston opted for a strapless, floor-length gown, complete with a pair of silky gloves, while Perry paired a classically '90s vest with an ill-fitting suit.
A mid-'90s British invasion came in the form of five bubbly ladies in some seriously flashy outfits. The Spice Girls celebrated girl power and individuality: Scary, Baby, Ginger, Sporty, and Posh each contributed unique looks that young women all over the world admired. We can credit the Spice Girls with the popularity of platform shoes, pigtail buns, and—of course—body glitter.
At the 50th Annual Primetime Emmy Awards in 1998, style icon Halle Berry walked the red carpet in a so-pretty, bejeweled gown and tiny sunglasses. It goes without saying that this outfit has definitely been recreated in recent years.
Post-Winona, Depp took up with Kate Moss—a duo that became arguably as iconic as the gothic exes. In 1995, they arrived at a Los Angeles premiere looking the part of a high-fashion pair.
Moss and Depp also shined style-wise off the red carpet—the couple dressed down in sleek coats and leather boots for the perfect combination of disheveled and chic.
SJP arrived at the 49th Annual Tony Awards in 1995 in the '90s outfit of our dreams: a part-silky, part-sheer dress topped off with a pair of strappy, silver sandals.
As one of the most beloved couples of the '90s, Brad and Gwyneth's relationship was well-documented until the pair parted ways in 1997. The duo was often photographed on the red carpet in coordinating outfits—and for a short period, matching haircuts—and their looks spanned the spectrum of '90s trends, from stark minimalism to grunge to preppy chic.
That hair! That billowing shirt! How can the man, the myth, the legend not be considered a '90s fashion icon?
My So Called Life meets Heathers! Winona Ryder and Claire Danes debuted matching pixie cuts and badass dresses at the Los Angeles Fire and Ice Ball in 1996.
If one thing is clear about red carpet events of the '90s, it's that SJP had a knack for arriving in outfits that only she could pull off. Here, Parker wears an early version of "the naked dress" to the VH1 Vogue Fashion Awards.
Even though they were just a pair of tykes at the time, the Olsen twins were the epitome of '90s fashion. Exhibit A: The twins (epically) walked a red-carpet movie premiere in matching, tiny sunglasses and monochromatic outfits.
The lace! The shawl! The hair! Nicole Kidman looked to be the belle of the ball in an epic '90s look at the American Film Institute Awards in Melbourne.
It's no secret that the ladies of Destiny's Child had their outfits down. Here, the group posed in matching fabric at the The London Aquarium. If a photo like this doesn't make you want to start a girl group right this very second, you aren't looking close enough.
Even before she owned the box office in the early aughts with classics like Bring It On and Spider-Man, Kirsten Dunst had a way of making an impression at events. In 1998, she attended the 8th Annual Environmental Media Awards in Los Angeles wearing a strappy black-floral dress and Mary Janes (the shoe that you and the rest of the world probably owned multiple pairs of in the '90s).
A pregnant Jada Pinkett Smith attended the Woo premiere in 1998 wearing the Ultimate '90s 'Fit: Maternity Addition. The actress paired an all-black jumpsuit with a sheer, button-down top. And what would a red carpet be without a pair of tiny sunglasses?
The late '90s ushered in an era of bubblegum pop, with Britney Spears leading the pack. Her sexy, belly-baring schoolgirl uniform in the video for "…Baby One More Time" paved the way for the low-slung jeans, navel rings, miniskirts, and bedazzled tank tops that would characterize the end of the decade's style.
Supermodels Naomi Campbell and Kate Moss reigned Queens of the '90s Modeling World. They were spotted, towards the end of the decade, at the Versace Diamonds are Forever show in London wearing the coolest, slinkiest slip dresses.
When TLC hit the scene, the music world went nuts—the drama! The music! The money! The girl gang defined their style with baggy athleisure pants, oversized tees and sweatshirts, and cropped tops. Their coordinating outfits epitomized an era of in-sync girl squads.
Towards the end of the decade, Campbell stunned at the UNICEF party in London—the model contrasted her vibrant dress and matching shoes with a bright-white bag.
The face of the SoCal ska-punk movement happened to be a ball of energy by the name of Gwen Stefani. The No Doubt frontwoman was known for her athletic build and style, often performing in nothing but cargo pants and a cropped beater. Here she is perfecting the art of matching your hair with your shoes.
Cameron Diaz's outfit at the 56th Annual Golden Globe Awards in 1999 was so freaking '90s it hurts. The actress paired grungy eye makeup and crimped hair with a pant-dress combo and tiny purse.
At the 1999 ESPY Awards, supermodel and fashion icon Tyra Banks wore an ultra-coordinating look—her rose hair clips matched the floral print on her dress and shoes.
Cindy Crawford wore this now-iconic Versace dress at the Rock N' Rule Benefit For AmFar. It's not hard to see why it made such an impact!
Fashion in the '90s was all about going back to the basics: a good button-down, a trusty pair of jeans, and simple, clean makeup. This outfit that Reese Witherspoon wore in 1994 checks all the right boxes.
I'll leave this here in case you needed more proof that Destiny's Child were some of the OG fashion icons! The group rocked purple from head to toe at the 13th Soul Train Music Awards back in 1999.
Paltrow went on to win the Oscar for Best Actress for her role in Shakespeare in Love while wearing this classic bubblegum pink Ralph Lauren gown way back in 1999—and it still remains a classic to this day.
The year was 1999 and the Met Gala theme was "Rock Style," so who better to don some edgy graphic tees than Liv Tyler and Stella McCartney? McCartney made these tees for them both on the day of the gala and it worked!
The '90s were all about the classic slip dresses, and no one wore them quite as well as Jennifer Lopez did over the course of the decade. Case in point: she donned this slinky sheer number for the 17th Annual CFDA Awards in 1998.
Talk about a power couple! Iman and David Bowie had many fashionable moments throughout the '90s, but this coordinating look of theirs at the 69th Regiment Armory in 1990 is one of the best.
Hayek wore this beaded Armani gown to her first-ever Oscars in 1997—and may have single-handedly started the tiara trend as a result.
A longtime lover of all things glittery, Shania Twain rocked this sequined turtleneck gown to the GRAMMY Awards back in 1999.
This is the definition of a daring couples look if I've ever seen one! The Beckhams wore head-to-toe leather outfits to the Versace Club Gala Party in London way back in 1999.
