11 of Lesser Known Celebrity Fashion Moments of the 90s

Winona Ryder wearing a spaghetti dress
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Last Updated on July 4, 2021

Celebrity culture in the 90s was absolutely booming. Supermodels were at their most dazzling, sitcoms reigned supreme, and media coverage via MTV, E!, and magazines exposed us to celebrities and their fashion choices constantly. 

Instead of rehashing the 90s looks that we all know through and through (Ginger’s Union Jack dress, Britney’s schoolgirl get-up, Princess Diana’s black revenge dress or Rachel Green’s haircut), let’s find lesser-known but just as inspiring celebrity style looks. 

Here are our top picks for the best 90s celebrity fashion moments, with tips for how to wear the looks today. 

Let’s take a trip down sartorial memory lane! 

Cyndi Crawford’s 1992 Super Bowl Pepsi Ad 

Cyndi Crawford’s mesmerizing beauty and incredible body graced the entire 90s, but she really made her mark in the 1992 Super Bowl Pepsi advertisement. Cyndi wore a simple pair of denim cut-off shorts, a white tank, and white gold hoop earrings.

The look was effortless and simple, highlighting Cyndi’s luscious hair, dark full lips, and dark eyes. It was a celebration of beauty, sex appeal, and the “all-American girl” simple style. 

Make it yours: 

  • Try high-waisted or mid-rise cropped jeans over a scoop-neck white long-sleeved bodysuit for cooler seasons 
  • Get the luscious supermodel look by using large round barrel curlers to get that “big hair” aesthetic, fill in the brows, use a dark brown kohl eyeliner to smoke the eyes, and dab on a pink-nude lipstick or balm 

Versace’s 1994 Campaign with Metallic Minis and Cropped Sweaters 

Versace’s sexy style was all the rage in the 90s, with one of the most memorable images being the 1994 campaign. Five supermodels wore teeny metallic mini skirts, cropped turtleneck sweaters, heels with socks, tanned skin, and 90s “neutral sexy” makeup. It was tacky (in the best way), raunchy, playful, and clearly demonstrated the power of the 90s supermodel. 

Make it yours: 

  • Emulate the shine-finish texture of the skirt with a leather or faux leather high-waisted mini matched with a cropped sweater, stockings, and ankle boots 

Halle Berry’s Lilac Dream at the 1996 Oscars 

Halle Berry turned up to the 1996 Academy Awards in one of the prettiest gowns of the decade. The lavender Valentino gown was made from shimmering velvet with a cowl neckline, softly ruched bodice, and 3D floral straps.

An asymmetrical satin overlay added extra light-catching textural contrast. The look was completed with a gauzy lavender shawl around Halle’s neck. 

Make it yours: 

  • Find a velvet cowl-neck top and pair with a satin or silk bias-cut midi-skirt in lilac or lavender 
  • Try a 90s-inspired makeup look with a dark plum lip liner with a slightly paler mauve lipstick, smoky kohl-rimmed eyes, and matte-satin skin 

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Winona Ryder’s Purple Velvet Slip Dress on a 1993 Red Carpet 

Winona was a grungy goddess in the 90s, wearing leather jackets, blue jeans, graphic tees, dark lipstick, and darker hair. She was also a champion of the roomy pantsuit, such as a baggy chocolate brown double-breasted ensemble, and a relaxed-fit black suit with a high-neck top. 

But it was a simple purple velvet slip dress that she wore on a 1993 red carpet that really caught our eye. The maxi slip dress in a witchy purple velvet had a low V-neck, straight cut that pooled slightly at the feet, and was worn (we think) braless.

Winona accessorized with the ultimate 90s addition, a black choker necklace with a silver pendant. Another perfect example of understated 90s red-carpet style. 

Make it yours: 

  • Layer a loose, slouchy velvet midi dress with an oversized black leather jacket and flats or western boots 
  • Find a burn-out patterned velvet cowl-neck midi or maxi dress and pair with strappy heels and gauzy chiffon scarf 

Read: Essential Style Guide: Grunge Outfits for Every Season and Look (Women’s Edition)

Kate Moss’s 1993 Naked Silver Dress 

Kate Moss, the impish beauty that shook the fashion world in the 90s (and ushered in the waif look) wore countless stellar looks. However, one particularly memorable moment was when she wore an ultra-sheer silver maxi slip dress with black briefs and no bra.

The dress was like liquid silver, with super thin straps, a low neckline, and floor-skimming bias-cut hemline. Kate’s stunning face was practically makeup-free, and her hair was casually swept back. She was the picture of youthfulness and carefree fun.

Make it yours: 

  • Find an opaque silver satin or silk bias-cut spaghetti strap dress and wear with simple, understated flats, a barely-there makeup look, and messy hair. Aim for a juxtaposition of regal, opulent fabric with a grungy, “threw it together” approach

Read: Slip Dress Outfit Style Guide: How to Wear a Slip Dress with Versatility

Julia Roberts’ Menswear Suit at the 1990s Golden Globe Awards 

Julia Roberts walked the red carpet at the 1990 Golden Globe Awards wearing a menswear suit, complete with tie and brown leather dress shoes. The suit was not a “feminized” or cinched version of a suit, it was a true menswear suit through and through.

It was baggy, sensibly grey, and completely shrouded her figure, but was effortlessly chic and sexy at the same time. Her unruly red curls were out in full, unkempt force, and her makeup was authentically 90s with a pale matte base, brick-brown lips, and subtly shaded eyes. 

Make it yours: 

  • If you have a father, a male partner, or a friend who wears suits to work, give one a try. It may sound a little silly, but give it a go! See how the suit feels and looks, and work from there to find your own version of the perfect suit 
  • Don’t be afraid to go with roomier styles, not everything needs to be molded to the body and tailored to within an inch of life

Buffy the Vampire Slayer’s Leopard Print and Leather 

‘Buffy the Vampire Slayer’ is a relic of TV treasure and a well of 90s fashion inspiration. Buffy was partial to animal print in the form of tanks and mini dresses, black leather jackets and boots, and those iconic red leather pants. The silhouettes were clean, often a-line or straight-cut, with short hemlines and knee-high boots perfect for kicking behinds. 

Make it yours: 

  • Pair a straight leather midi-skirt with a plain tank, tee, or blouse (weather-dependant) and a pair of leopard-print pumps
  • Try an a-line leopard-print mini with knee-high leather boots, sheer stockings, and a slouchy knit sweater 

Christy Turlington’s beige suit and tan belt 

Supermodel Christy Turlington was a big fan of the pantsuit in the 80s and 90s, being snapped in catalogs, runways, and on red carpets in beige or cream-toned suits. The suits were simply accented with plain white blouses or tees, leather belts, and matching leather flats. The look was a fusion of professional-chic, equestrian, preppiness, and high-class conservative style. 

Make it yours: 

  • Try on a range of suits to find your perfect fit, or have it tailored if need be. Pick a suit that is versatile so you can wear both pieces as separates with your staple wardrobe garments
  • If you’re tall and willowy, try an oversized suit with front-pleated trousers and a roomy blazer 

Liv Tyler’s tartan mini and sweater in ‘Empire Records’

‘Empire Records’ should be on your “must-watch” films list because it’s truly excellent. Liv Tyler, Renee Zellweger, and the cast served many memorable looks involving grungy sweaters, cropped cardigans worn open with tiny mini skirts, tank tops, Converse, and sleeveless shirts.

However, the most defining look was worn by the beautiful Liv Tyler: a tartan wrap mini skirt, a cropped blue sweater and chunky Doc Marten boots. The look seamlessly fused sexy and grunge. 

Make it yours: 

  • For extra coverage, pick a tartan midi-skirt with a straight or pencil cut and a high-waist
  • Try a cropped wrap-style cardigan with a low V, or a boxy, off-the-shoulder slouchy cropped cardigan
  • Streamline the look with heeled ankle boots, or a pair of knee-high leather boots 

Leonardo DiCaprio’s Hawaiian shirt in ‘Romeo and Juliet’

When Baz Luhrmann’s ‘Romeo and Juliet’ hit the screens in 1996, the world fell in love with Leonardo DiCaprio as soon as they saw him with his floppy hair, boyish charm, and blue floral shirt with Japanese-style print. This was an iconic moment for fashion, our hearts, and Leo’s acting career. 

Make it yours: 

  • Fuse the holiday-chic Hawaiian shirt with clean-cut workwear by tucking a short-sleeved Hawaiian shirt into a pair of high-waisted black cigarette trousers, a satin-lapel blazer, and heels 
  • Wear a Hawaiian shirt open and loose over your bikini or one-piece with denim cut-offs in Summer. Sun protection and style in one, (our favourite combo)

Read: 90s Japanese Fashion Trends

Julia Stiles’ Low-Rise Pants and cropped tank top from ‘10 Things I Hate About You’

‘10 Things I Hate About You’ is one of the best teen movies ever made, hands down. Heath Ledger (rest in peace) won our hearts, while Julia Stiles taught us how to stand up for ourselves.

There are countless fashion gems in this movie, but the one that sticks out is Kat’s house party outfit she wore the night she danced on the table and vomited after gazing into Patrick’s “a little green in them” eyes. She wore a black leather jacket (which came off), a taupe midriff tank and low-rise boot-cut trousers in a satin finish. 

Make it yours: 

  • Find a pair of pants made from thick, embossed stretch satin with a higher waist (a little more flattering and comfortable) and a straight leg. Pair with a waffle-finish loose cotton tank and leather lace-ups