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.
Pamela Anderson
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.
Brooke Shields
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.
Christy Turlington
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.
Shalom Harlow
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?
Brittany Murphy
Confirmed: the sheer trend started in the '90s, and on Brittany Murphy specifically. This grungy ensemble from 1999 would totally work today.
Mary-Kate and Ashley Olsen
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.
Angelina Jolie
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.
Halle Berry
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.
Madonna and Michael Jackson
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.
Fran Drescher
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).
Tia and Tamera Mowry
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.
Lenny Kravitz and Lisa Bonet
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.
Drew Barrymore
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.
Madonna
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.
Alicia Silverstone
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).
Chloë Sevigny
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.
Winona Ryder
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.
Winona Ryder and Johnny Depp
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.
Courtney Love and Kurt Cobain
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.
Princess Diana
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.
Elizabeth Hurley and Hugh Grant
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.
Katie Holmes and James Van Der Beek
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).
Sarah Jessica Parker
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.
Jennifer Aniston and Matthew Perry
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.
The Spice Girls
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.
Brad Pitt and Gwyneth Paltrow
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.
Sarah Jessica Parker
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.
Mary-Kate and Ashley Olsen
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.
Kirsten Dunst
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).
Britney Spears
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.
Naomi Campbell and Kate Moss
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.
Gwen Stefani
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.
