The most iconic ‘90s outfits that made fashion history

From red carpets to movie screens, the 1990s were a golden era for style statements that did more than just look good—they shifted culture. And with celebrities now increasingly turning to iconic fashion moments from the past—or even sourcing the exact looks—for events like the Met Gala, revisiting these legendary outfits feels all the more timely. Here’s how these unforgettable ‘90s outfits made their mark—and why they’re still referenced in fashion today.

Princess Diana’s revenge dress (1994)

On the same night Prince Charles admitted to infidelity on national TV, Diana stepped out in a striking black Christina Stambolian dress that broke every fashion rule that governed the royal family. Royals rarely wore black outside of mourning, and certainly not form-fitting, off-the-shoulder LBDs. It was the first time Diana wore something this revealing in the public eye—and it sent shockwaves. Dubbed as the “revenge dress” by the media, it became a symbol of her independence, confidence, and refusal to be sidelined.

Elizabeth Hurley’s safety-pin Versace gown (1994)

Liz Hurley was relatively unknown when she walked the Four Weddings and a Funeral premiere red carpet on Hugh Grant’s arm—but that changed overnight. The daring, gold safety-pin dress designed by Gianni Versace became an instant fashion legend and put both Hurley and the brand on the pop culture map. It redefined red carpet boundaries for years to come, and even Hurley claims this last moment press pick opened doors for her in her career.

Claudia Schiffer’s Chanel couture look (1992)

When Claudia Schiffer walked the runway as the Chanel bride in 1992—wearing an ornate, pearl-studded couture gown by Karl Lagerfeld—she looked like a modern-day Marie Antoinette. As Lagerfeld’s muse, she fully owned the moment and made headlines. The gown went on to become one of the most defining bridal looks of the decade, and its legacy held strong years later. Dua Lipa brought it back into the spotlight at the 2023 Met Gala, and Alia Bhatt also paid homage by wearing a Prabal Gurung gown inspired by the iconic couture piece. Schiffer’s bridal moment clearly knows how to make a statement, even decades later.

Christy Turlington’s Chanel gold chain dress (1992)

Another iconic Karl Lagerfeld creation, this gold chain mini dress worn by Christy Turlington on the Chanel runway in 1992 turned heads for all the right reasons. With layers of cascading chains and medallions, it was daring, decadent, and pure ‘90s opulence. Designed like wearable art, the dress captured the bold energy of the era, and its influence didn’t stop there. Penélope Cruz slipped into the dramatic dress in Broken Embraces (2009), and Lily-Rose Depp resurrected it for the 2019 Met Gala. A reminder that Lagerfeld knew exactly how to craft pieces that would live on far beyond the runway.

Julia Roberts’ red gown in Pretty Woman (1990)

The moment Vivian stepped out wearing the structured red gown—custom-designed by Marilyn Vance—for her night at the opera in Pretty Woman, the audience (and Richard Gere’s character) was floored. The visual transformation was so powerful that it felt truly magical, and viewers watching the film felt it too. The look became a cinematic touchstone for “the makeover moment” in romantic comedies—and even today, the timeless appeal of the red dress lives on.

Sharon Stone’s white dress in Basic Instinct (1992)

This minimal white turtleneck dress by Ellen Mirojnick became one of the most controversial film costumes in history. Worn in that interrogation scene of Basic Instinct, where Stone's character crosses and uncrosses her legs, the outfit’s stark simplicity only heightened the shock value. The moment sparked global conversation, censorship debates, and solidified Stone’s femme fatale status.

Madonna’s cone bra by Jean Paul Gaultier (1990)

When Madonna unveiled the now-iconic pink satin cone bra corset during her 1990 Blond Ambition Tour, she didn't just perform—she provoked. Designed by Jean Paul Gaultier, the sharply structured, pointy silhouette was inspired by 1950s bullet bras and transformed into a symbol of female empowerment and rebellion. The audacious design challenged traditional norms, blending lingerie with outerwear, and became one of the most talked-about stage costumes in music history. Decades later, the cone bra lives on—reimagined by the likes of Cardi B in a Gaultier-inspired look, Beyoncé during her Renaissance tour, and even resurfacing on the runway in Jean Paul Gaultier’s own tribute collections.

Cher Horowitz’s yellow plaid set in Clueless (1995)

Designed by Mona May, the iconic checkered blazer and skirt set became Clueless’s most recognisable look. From Halloween costumes to high fashion editorials, the ensemble had a long afterlife, including a pop culture comeback in Iggy Azalea’s “Fancy” music video decades later. It proved that fashion-savvy teenage girls could be style tastemakers in their own right.

Jennifer Aniston’s mint green dress in Friends (1996)

In The One Where No One’s Ready episode of Friends season 3, while Ross is stressing over getting everyone out the door, Rachel is having a full-blown outfit crisis. But when she finally steps out in that sleek, mint green column dress designed by Sally LaPointe, time practically stops. It wasn’t loud or over-the-top—but it was a peak Rachel Green style moment: understated, cool, and so effortlessly chic. It’s pretty much when everyone in that decade started wanting to be “that girl”—aka Rachel Green. 

Kate Moss’s sheer metallic slip dress (1993)

Worn to an Elite Model Agency party when she was just 19, Kate Moss’s sheer metallic slip dress by Liza Bruce was accidental fashion history. She later revealed she had no idea it would turn that see-through under flash photography. But the images of Moss smiling, carefree, and unapologetically herself, became legendary. The moment captured the raw, effortless cool of the ‘90s and helped usher in the rise of sheer outfits and the “heroin chic” aesthetic, while also cementing the slip dress as a full-on ‘90s fashion trend.  Minimal, unfiltered, and totally iconic.

Sarah Jessica Parker’s “naked dress” in Sex and the City (1998)

First seen in the pilot episode of SATC, Carrie Bradshaw’s blush-toned DKNY slip dress was what she wore on her first date with Mr. Big. In the show, it was cheekily referred to as the “naked dress” because it looked like she was wearing nothing at all—cue instant icon status. The dress became a symbol of Carrie’s fearless femininity and, much like Moss’s slip dress, helped solidify the ‘90s slip dress trend in real life.

Each of these looks did more than follow a trend—they started one. Whether by shifting red carpet standards, redefining female agency, or simply proving the power of a strong silhouette, these looks proved that fashion can define a moment—and keep echoing for decades.

Lead image: Getty

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