25 Celebrity Fashion Moments That Defined the '90s

Madonna infamously passed by the Plaza Hotel in New York wearing this stylish black outfit like a true material girl. Here, she played around with textures, contrasting fishnet details with a shiny vinyl jacket. To top it off, effortless brown, round sunglasses and a dark-red lip gave her look a pop of color.

Julia Roberts went to the Golden Globes in 1990 in this boxy Diane Keaton-esque suit and returned home with a win for her role in Steel Magnolias. Completed with a purple jacquard tie, the androgynous outfit went down in history as one of Roberts’s most iconic looks.

Model Cindy Crawford debuted this iconic deep-plunge red Versace dress at the 63rd Academy Awards in 1991.

Rivaling Beetlejuice fashion icon Lydia Deetz, Winona Ryder embodied ’90s grunge with this edgy ensemble, styling a leather jacket with a graphic tee and fitted jeans while attending the premiere of The Commitments.

Geena Davis gave us ’90s princess vibes at the 64th Academy Awards with a long, ruffly dress train. The Thelma and Louise actress complemented her outfit with pearls, sheer tights, white gloves, and whimsical black shoes for a glam-punk look.

Halle Berry‘s fitted strapless red dress in 1992 embodied pure elegance. The Boomerang actress wore the gown at the 24th annual NAACP Image Awards with chic drop earrings and classic black heels.

Models Kate Moss and Naomi Campbell were a stylish force to be reckoned with at London Fashion Week in 1993. Moss paired her statement fur-trimmed coat with a white blouse and gray miniskirt, while Campbell punched up her plaid dress with electric-blue thigh-high socks and platform shoes.

Just a year before her tragic death, Selena wore this dazzling crystal-covered white halter dress to the 1994 Grammys, adding a pop of color with her signature red lips.

Princess Diana’s Christina Stambolian gown has infamously been dubbed “the revenge dress,” as she wore it after separating from Prince Charles. The people’s princess elevated this outfit with a pearl choker and sheer tights for an effortlessly sexy look.

Janet Jackson celebrated her sold-out concert tour in 1994 by pairing a timeless cropped turtleneck with distressed jeans for a street-chic look.

Drew Barrymore tapped into a classic Hollywood glamour style by wearing a black dress with a sweetheart neckline at the VMAs in 1995. For a whimsical touch, she added two pretty daisies in her hair.

The Clueless star’s black blazer, plaid skirt, and high white socks still have us totally buggin’ decades later.

A casual-chic fashion icon, Gwyneth Paltrow matched a stylish animal-print jacket with an all-black ensemble and laid-back sneakers at the From Dusk Till Dawn premiere.

Lisa Bonet attended The Aristocats‘ 1996 video release premiere in both an edgy and laid-back look of a brown maxi skirt paired with a silk onyx blouse. It’s clear that Zoë Kravitz gets some of her stylish sensibilities from her mom!

Mary J. Blige wore leopard print from head to toe for her 1996 Grammys look. She accessorized in neutral black sunnies, gloves, and shoes to balance her wild ensemble.

Long before she launched her charming Southern fashion brand Draper James, Reese Witherspoon donned a couple of edgy outfits back in the ’90s. At the Two Days in the Valley premiere, she turned heads by pairing this red leather jacket with an all-black ensemble.

Sharon Stone kept it sleek and simple with a beautiful velvet Armani coat (and a Gap shirt) at the 1996 Academy Awards, accessorizing with a white flower and pair of earrings.

Nicole Kidman exuded elegance with this satin chartreuse dress at the 69th Academy Awards. The intricate floral detailing and side slit added even more allure to this dazzling outfit.

Thin straps defined this sleek and quintessentially ’90s little black dress look that Jennifer Aniston wore at her Cosmopolitan cover party in 1997.

Mariah Carey‘s black two-piece outfit stunned at the 1997 VMAs. The thin straps on her top and heels paired beautifully with her high-slit skirt for a memorable look.

At the Return to Paradise premiere, Jada Pinkett Smith made a statement with this bold, long leather jacket, completing her look with sexy strappy heels.

Cowgirl chic was the main vibe of this edgy look Jennifer Lopez wore to the VMAs; it consisted of an oversize blazer, crop top, and, of course, wide-brimmed hat.

Angela Bassett looked divine in this green satin one-shoulder dress at the How Stella Got Her Groove Back premiere in 1998. The thin orange accents added a pop of contrast, and she finished the outfit with effortless strappy sandals.

The fur trimming on Lucy Liu‘s red suede coat at the Go premiere was simply iconic. The actress kept it sleek with a neutral black outfit underneath her statement outerwear.

Actress and model Elizabeth Hurley walked in this stunning pink leather outfit at the Mickey Blue Eyes premiere so Elle Woods could run in Legally Blonde.