30 Years Later, These Iconic ‘90s Outfits Look Just as Chic Now as They Did Then
Worn at a time when Nirvana was on the radio and Karl Lagerfeld was at Chanel, these iconic '90s outfits showcase the best style the decade had to offer.

- The 16 Most Iconic '90s Outfits
- 1. Kate Moss's Slip Dress
- 2. Victoria Beckham's Chainmail Halterneck Top
- 3. Princess Diana's Revenge Dress
- 4. Carolyn Bessette-Kennedy's Street Style
- 5. Jennifer Lopez's Waistcoat Dress
- 6. Mariah Carey's MTV VMAs Two-Piece
- 7. Gwyneth Paltrow's Tom Ford for Gucci Suit
- 8. Céline Dion's Backwards John Galliano Suit
- 9. Iman's Floral Dress
- 10. Julia Roberts's Armani Men's Suit
- 11. Winona Ryder's Casual Film Premiere Look
- 12. Halle Berry's Airport Outfit
- 13. Jennifer Aniston's New York Off-Duty Outfit
- 14. Pamela Anderson's Vivienne Westwood Corset
- 15. Chloë Sevigny's Tiger Print Stockings
- 16. Naomi Campbell's Vivienne Westwood Platforms
When I think of iconic ‘90s outfits, my mind instantly wanders to a few pivotal points during the decade. There's the '90s fashion cemented in popular culture, like Carrie Bradshaw’s eminently eclectic designer wardrobing on Sex and the City or Monica Geller’s considerate casualness in Friends.
Then there are the runway moments, including but not limited to Versace’s Freedom! Climax in 1991, whereby Linda Evangelista, Christy Turlington, Cindy Crawford and Naomi Campbell closed the show dressed in monochromatic shift mini dresses and mouthing the lyrics of George Michael’s anthem, Marc Jacobs’ grunge collection for Perry Ellis in 1994 and Mugler’s haute couture cyborg suit from 1995.
On stage, there was no shortage of spotlight-stealing ensembles, including Madonna’s Jean Paul Gaultier cone bra, which she wore during her 1990 Blonde Ambition world tour, or TLC’s genre-defying and gender-bending matching streetwear.
The red carpet forays are equally momentous, like Elizabeth Hurley’s slinky safety pin dress from the premiere of Four Weddings and a Funeral or the chartreuse chinoiserie Dior by John Galliano gown Nicole Kidman wore to the 69th annual Academy Awards in 1997.
However, as someone whose credentials to comment on the matter include being born six months before the turn of the 21st century in the June of 1999, the most iconic ‘90s outfits aren’t the ones you’ll find on screen or played up for an audience. Instead, the decade’s biggest contributions come in a more insouciant approach, like model off-duty sightings or the days celebrities went to events without being dressed by a stylist.
To me, the most iconic ‘90s outfits stand as a time capsule. They reflect what personal style looked like without the influence of niche aesthetics, self-surveilling social media or the ability to commodify your outfit of the day through brand deals and paparazzi shots. As Cindy Crawford said during an interview meditating on her life in looks, “No one put [my outfit] together other than just what I grabbed.”
From Princess Diana’s revenge dress, Oscar appearances no one saw coming and Posh and Becks's most recognisable look, uncover the 16 most iconic ‘90s outfits of all time, ahead.
The 16 Most Iconic '90s Outfits
1. Kate Moss's Slip Dress
Style Notes: Cherubic and fresh from Croydon, Kate Moss began the decade by gracing the cover of The Face's July 1990 issue. She might've been only 16 at the time, but only three years later, she would go on to wear a look that defined the '90s. Indeed, her humble slip dress was slinky, lingerie-inspired and, according to an interview she gave in 2023, unknowingly "see-through".
"The pictures came out the next day in the newspaper, and it was the flash that made it look 'naked'," Moss said of the Liza Bruce piece, which she wore to the Elite Model Agency party for the Look of the Year in 1993.
Shop the Outfit:
This Other Stories slip combines three '90s fashion trend; a slip bodice, lace trim and handkerchief hem.
2. Victoria Beckham's Chainmail Halterneck Top
Style Notes: A power couple if there ever was one, David and Victoria Beckham's '90s fashion gave way to the mode of coordinating style to strengthen one's public persona. On their own, the Spice Girl and the English footballer had flair in spades. But it was when they were spotted out together wearing similar outfits that piqued interest the most. This look, which was worn to an event in London in 1999, is one of the former pop star turned fashion designer's more demure. Still, the combination of the chintzy halterneck top and animal-print shoe remains one of the best in her oeuvre.
Shop the Outfit:
This feels like the antithesis of the more sophisticated looks Victoria Beckham wears nowadays, while nevertheless timeless.
She paired her party top with a darker wash of denim, though I think these grey jeans are more relevant for today.
These wedges are the 2025 equivalent to VB's pointed-toe boots.
3. Princess Diana's Revenge Dress
Style Notes: Princess Diana's revenge dress is, in my opinion, the most iconic '90s outfit. Not only is this gown a symbol of her use of fashion as a form of rebellion and silent strength, but the acme of how the late Lady Spencer approached her role in the royal family. For the uninitiated, the former Princess of Wales wore this little black dress to a gala in Hyde Park's Serpentine Gallery on the same night the now King Charles III confessed to committing adultery during their marriage during a televised interview. So, what do you wear when your ex-husband and heir to the throne reveals to have cheated on you to the public? A fitted and strapless Christina Stambolian design with a floaty chiffon train, of course.
Shop the Outfit:
If you're asking yourself 'what to wear to a black-tie event', I think I've just found the answer...
4. Carolyn Bessette-Kennedy's Street Style
Style Notes: Carolyn Bessette-Kennedy has come back into the zeitgeist with the impending release and current production of Ryan Murphy's upcoming limited series, American Love Story. The furore around the historically inaccurate costuming proves exactly why CBK's fashion legacy remains perennially inimitable. Her unwavering commitment to minimalism set a precedent that Manhattan darlings still follow today. Of course, as a publicist for Calvin Klein, her wardrobe was always functional and apt for corporate settings, meaning workwear staples like white button-down shirts and midi skirts were always present, yet nonetheless designer, given her penchant for Prada, Miu Miu and Yohji Yamamoto.
Shop the Outfit:
5. Jennifer Lopez's Waistcoat Dress
Style Notes: Her hit single "Jenny From The Block" mightn't even hit the airwaves by the time this picture was taken, but Jennifer Lopez's '90s fashion era is proof that the New Yorker has always been a force to contend with. A smidge more mindful than the glamorous outfits that succeeded the decade in the early 2000s, this waistcoat dress epitomises her girl next door origins.
Shop the Outfit:
Despite originating in the '70s, even '90s babies loved clogs, too.
6. Mariah Carey's MTV VMAs Two-Piece
Style Notes: Taking a page from Princess Diana's book, Mariah Carey put her own spin on revenge dressing when she attended the 1997 MTV Video Music Awards wearing a sultry two-piece set after announcing her split from then-husband Tommy Mottola. The simplicity of the co-ord really demonstrates why minimalism was so pervasive. (See: clean lines and unfussy elegance.)
Shop the Outfit:
Ideal for styling with a classic white t-shirt.
7. Gwyneth Paltrow's Tom Ford for Gucci Suit
Style Notes: Gwyneth Paltrow might've helped pioneer terms like "conscious uncoupling" and a well-rounded lifestyle that involves dry brushing, infrared saunas, and yoni eggs, but before she was the Goop juggernaut we know her to be, she was an actress with a street style that focused on refined ease. This came to the forefront in 1996, when Paltrow wore a burgundy Gucci suit designed by Tom Ford to the MTV VMAs. The suit was fresh of the runway, having made its debut in the autumn/winter season that year, showcasing her know-how and ability to make effortless and well-tailored pieces covetable as far back as 30 years ago. In 2022, Paltrow rewore this look for Gucci's Hollywood-inspired Love Parade collection, wearing a recreation designed by Alessandro Michele for the Florentine maison's Aria collection a year earlier.
Shop the Outfit:
8. Céline Dion's Backwards John Galliano Suit
Style Notes: Céline Dion's recent documentary might have helped thrust the French-Canadian diva's style philosophy into the spotlight. (If you haven't seen, she confessed to owning over 10,000 pairs of shoes and will buy any style she likes regardless of size: "I walk the shoe, the shoe don't walk me".) Even all the way back in 1999 was she living by her own rules, like the time she attend the 71st Academy Awards wearing a John Galliano for Dior suit backwards.
Shop the Outfit:
The definition of an expensive-looking high-street find.
The avant-garde curved heel makes this pair Céline-approved.
9. Iman's Floral Dress
Style Notes: While Posh and Becks catapulted their stardom through matching outfits, the opposite could be said for David Bowie and legendary supermodel Iman. He was the androgynous rockstar, and she was the fashion vixen, which is really apparent in this outing to the 1999 MTV VMAs. While the Ziggy Stardust singer's outfit looks like something you'd find at The Row, Iman is a vision in this floral, body-conscious dress.
Shop the Outfit:
A that can take you from the red carpet to a wedding and a black-tie event.
You'll find a pair of heels like these in every French woman's wardrobe.
10. Julia Roberts's Armani Men's Suit
Style Notes: From the underarm hair-exposing red sequin Vivienne Tam dress that she wore to the premiere of Notting Hill to her infamous pre and post-makeover Pretty Woman costumes, Julia Roberts is synonymous with iconic '90s outfits. However, the one that feels the most timeless is this Giorgio Armani men's suit that she wore to the 1990 Golden Globes. Taking home the prestigious award for Best Supporting Actress for her performance in Steel Magnolias, she did so wearing the tailored two-piece that she picked up earlier on Rodeo Drive. (Very Vivian Ward of her!) Remaining on moodboards ever since, Ayo Edebiri recreated the look in a Loewe version for the 2025 ceremony.
Shop the Outfit:
This pinstripe version feels particularly on-trend, especially following the reign of this style at the 2025 Met Gala.
11. Winona Ryder's Casual Film Premiere Look
Style Notes: As a formidable child star who broke out into the mainstream during the '80s Brat Pack era, by the time the '90s rolled around, Winona Ryder was a seasoned professional in Hollywood spheres. This look from 1991 is one of her most unintentionally punk and indicative of how different the industry was back then. With this picture taken of the star on her way to a film premiere, her simple jeans and a nice top formula feels fresh, unpretentious and makes me nostalgic for a time when turning a look wasn't of paramount importance.
Shop the Outfit:
Why not embrace the '90s with Agolde's '90s straight-leg jeans?
12. Halle Berry's Airport Outfit
Style Notes: Take it from Halle Berry; jeans and a leather jacket are an undeniable '90s silhouette. This is a more relaxed take compared to Winona's, which makes it the perfect model for the iconic '90s airport outfits that were so prevalent during this time.
Shop the Outfit:
Available in so many sizes and numerous leg lengths, these Abercrombie Fitch jeans are a high-street best seller for a reason.
Swap the buckled loafer for this suede, boat shoe-inspired pair to bring the look into this decade.
13. Jennifer Aniston's New York Off-Duty Outfit
Style Notes: Jennifer Aniston might've introduced herself to the world via her bubbly, preppy and somewhat spoiled Friends character, Rachel Green. And while her costuming will always be relevant, her off-camera looks are equally enticing, too. Here, while shooting a film in 1997, she puts a '90s fashion twist on layering by teaming a strappy mini dress over a white t-shirt before tying it all together with a tied-up longsleeve, woven bag, backwards cap and a micro sunglasses.
Shop the Outfit:
A more body-conscious version of COS's editor-adored clean cut t-shirt.
The soft navy colouring of Anthropologie's viral Nola woven leather bag is such a premium addition.
14. Pamela Anderson's Vivienne Westwood Corset
Style Notes: When it comes to iconic '90s outfits, Pamela Anderson has certainly made a few entrances into the canon. From her bombshell all-leather looks during her Barb Wire press tour to the red swimsuit of her Baywatch era, and even the fuzzy pink hat she wore to the 1999 MTV VMAs, Anderson has done her part in etching this decade's fashion into the annals of history. Personally, I adore this more whimsical moment which took place in Australia in 1994. Wearing a Vivienne Westwood corset dress, the fairytale feeling of the garment contradicts her more vampy persona, making it an inspired choice on her part. Plus, the bubble skirt and brocade detailing remind me of something you'd find at the likes of Turner Vintage or Annie's Ibiza. If Pamela shopped at Portobello Road...
Shop the Outfit:
15. Chloë Sevigny's Tiger Print Stockings
Style Notes: One of the original it girls, Chloë Sevigny is the patron saint of iconic '90s outfits. Taken just after her debut in Larry Clarke's Kids and appearance in Miu Miu's spring/summer 1999 runway, this outfit captures Sevigny in her element, complete with a hodgepodge of high-fashion paraphernalia like tiger-print stockings and a rosette to adorn her velvet one-shoulder dress.
Shop the Outfit:
16. Naomi Campbell's Vivienne Westwood Platforms
Style Notes: This edit wouldn't be complete without an appearance from Naomi Campbell. As her recent solo exhibition at London's V&A Museum made apparent, the supermodel's wardrobe choices are nothing short of iconic, but I personally adore this Vivienne Westwood outfit that she wore to the Designer of the Year Awards at the Natural History Museum during London Fashion Week in 1993. Her choosing to don these Yves Klein blue thigh-high stockings and platform shoes came only months after she took a tumble on the designer's runway earlier that year. Her powerful reclamation of this moment is nothing short of legendary and proves why Campbell is so revered, respected and renowned as a fashion force.
Shop the Outfit:
Ava Gilchrist is the SEO Writer atBest Knockoff Luxury Clothing UK. Born in Sydney but now based in London, Ava has worked at some of the most prestigious women’s luxury and lifestyle publications including ELLE, Marie Claire and most recently GRAZIA where she held the title of Senior Fashion Features Writer. Ava has five years of industry experience, beginning her writing career after graduating with a Bachelor of Communication from the University of Technology, Sydney. Her words fuse style with substance, bringing readers insightful commentary on Wholesale Replica Bag fashion trends, runway shows, celebrity red carpet offerings, must-have shopping pieces, beauty hacks and pop cultural moments. As an editor, Ava has interviewed everyone from Kendall Jenner, Margot Robbie, Zendaya, Emma Corrin and Stella McCartney.
-
In the Hamptons, Apple Martin Wore the Skirt Trend That Screams "East-End Elite"
My ideal vacation outfit.
-
FYI: Sandal Haters in Ibiza Are Wearing Beach Dresses With This Unexpected Shoe Trend
Sporty and comfortable.
-
Gwyneth Paltrow's High-Caliber Shoe Trend Prevents LBDs From Looking Boring
Suddenly, I need a similar pair.
-
Black Heels Are Fine, But in Portofino, Everyone Knows That This Shoe Color Looks Chicer With Dresses
Just a suggestion.
-
Not Linen, Not Denim: The Far Chicer Pant Trend Fashion People in Turkey Are Wearing With White Tank Tops
Fashion icon Rosie Huntington-Whiteley approves.
-
The '90s Dress-and-Shoe Pairing It Girls Are Wearing to Parties in East Hampton (Sorry, Flip-Flops, You Weren't Invited)
Classic elegance spotted at Gucci's star-studded soirée on Long Island.
-
Just to Be Clear, *These* Are the Pants Fashion People in L.A. Are Wearing Instead of Basic Jeans
Spotted in Paris too.
-
This Is the Least-Scary Way to Wear the Sheer Clothing Trend
J.Law approved.