Few decades have seen changes in fashion as exciting, and stirring, as in the ’90s. The decade marked a tonal shift from the 1980s, which were synonymous with glitz, shoulder pads and big hair, and into clothes that were more comfortable, understated and considered. Brands like Miu Miu and Calvin Klein pushed clean-lined approaches to style that did away with excess, while style icons like Carolyn Bessette-Kennedy confirmed the adage that less is often more, and just as impactful.

But that doesn’t mean everyone played it safe. In fact, it was the opposite, for more liberated attitudes gave way to greater amounts of fashion experimentation. There were the dresses made by red-carpet enfant terrible Gianni Versace, whose risqué aesthetic was embraced by existing and emerging superstars on the red carpet, or those who, like Sharon Stone and Chloë Sevigny, were unafraid to flip conventionality on its head. Keep reading for them stirring histories behind these 15 red-carpet looks from the ’90s, which turned heads and set trends for all different reasons.

1991 – Cindy Crawford

Cindy Crawford’s early ’90s modelling fame was rare; she transcended the fashion world to become a pop culture fixture and household name (helped along by her famous 1992 Pepsi commercial). In 1991 she attended the Oscars with ex-husband Richard Gere and captivated crowds in this Versace dress, which would become one of the brand’s most-famous looks. At the rear it was backless, while a thigh-split came up the back that Crawford has said required careful and strategic movement around cameras. 

1991 – Jodie Foster

Jodie Foster is an unsung hero of fashion experimentation, something she exemplified while promoting her Oscar-winning performance in The Silence of the Lambs in 1991. At an event, she wore this glittery pin-striped blazer with nothing underneath—a visible defining shift between the bold glamour of the ’80s and the stripped-back, laid-bare minimalism that typified the ’90s, á la Prada and Calvin Klein.

1992 – Cindy Crawford

Minimalism may have become a fully formed concept in the ’90s, but that doesn’t mean glamour of the more extreme kind was obsolete. At the 1992 MTV VMAs, Cindy Crawford nabbed a dress from Gianni Versace’s autumn/winter ’92/’93 collection (worn on the runway by fellow super Christy Turlington Burns), a range that flirted with bondage and became controversial. Still, even if elements of this look are a little dated by today’s standards, the innovative corset silhouette has influenced many. 

1993 – Courtney Love

Any parent will tell you that sometimes, leaving your child with a carer just isn’t an option. In a move likely made of necessity, Courtney Love walked the red carpet at the 1993 MTV VMAs with her young daughter, Frances Bean Cobain, to support husband and alt-rock king Kurt Cobain. This kind of rock-and-roll approach to glamour would come to define Love’s style.

1994 – Claudia Schiffer

Gianni Versace knew how to create outfits that would be remembered forever on the red carpet. Though his most-referenced are often Cindy Crawford’s and Elizabeth Hurley’s (more on that below), this pink dress worn by Claudia Schiffer in 1994 featured his famous safety-pin motifs and pre-empted ‘Barbiecore’ by almost three decades.

1994 – Elizabeth Hurley

Few looks can transcend fashion to become cultural phenomena. But that’s exactly what happened when Elizabeth Hurley, who was a relatively unknown actress in 1994, attended the premiere of Four Weddings and a Funeral wearing a Versace dress that was loaned to her by the brand only hours before the event. Its innovative cut had all the bells and whistles we’d associate with the brand—deep cuts and gold safety pins among them—and turned Hurley into a star almost overnight, setting the standard for bold red carpet style to follow. 

1996 – Chloë Sevigny

Mixing a glittery black dress and open-toed shoes with leopard-print stockings is the kind of sartorial combination Chloë Sevigny would be best-suited to sell. The model and actress exploded onto the scene in the mid-’90s and wowed fashion with her unconventional approach—something that was noticed by Miuccia Prada, which landed Sevigny on the runway for Miu Miu as one of its original ambassadors. Nonetheless, this outfit was the start of the Kids actor’s taste-making that’s continued until now (never forget the pandemonium that ensued when she recently held an archive sale in New York). 

1996 – Gwyneth Paltrow

Women have always worn suits on red carpets, and did so long before Gwyneth Paltrow was seen in this red Gucci velvet one in 1996. That doesn’t mean this outfit, designed by Tom Ford in the early years of his career, flew under the radar. In fact, the opposite happened; Paltrow was praised and admired for her undying dedication to ’90s simplicity, as well as her ability to try any silhouette. It’s history—so much so, that she even rocked a new version at Gucci’s autumn/winter ’21/’22 show in Los Angeles, 25 years later.

1996 – Mary J. Blige

Leopard is divisive enough on its own, so wearing it head-to-toe—down to gloves and with a hood involved—is statement-making material. Mary J. Blige, always a fashion pioneer, tried such an outfit on for size while at the Grammys in 1996 and made fashion history. 

1997 – Natalie Portman

Two years before she appeared in Star Wars Episode 1: The Phantom Menace, Natalie Portman attended a film premiere and showed a taste in radical fashion designers that belied her 15 years. The Jean Paul Gaultier dress she wore may have been relatively undiscussed at the time but was preeminent, given the appetite among collectors and archivists for Gaultier’s ’90s mesh dresses that cropped up in the 2010s and 2020s (after receiving the Kardashian tick of approval).

1997 – Nicole Kidman

Nicole Kidman’s Dior by John Galliano dress at the 1997 Oscars didn’t cause a stir for how it looked, but rather for the circumstances attached to it. Disliked by some (including Joan Rivers, who infamously said the colour was unsightly and faux retched when she saw it), the gown marked a shift in the popularity of wearing haute couture on red carpets, something reflected today by the number of stars who pull directly from the couture runways in Paris for red carpets today.

1998 – Carmen Electra

This dress, designed by Stephen Sprouse and worn by Carmen Electra to the 1998 MTV Movie Awards, appeared to defy gravity, though a svelte cut and transparent back-strap are the real reasons it didn’t fall. 24 years later, the actress and model revealed she still owns the dress after Kim Kardashian paid homage to the moment on Instagram with a near-identical version of her own. 

1998 – Sharon Stone

Sharon Stone isn’t the only woman to pair a formal skirt with an unbuttoned white shirt for a red-carpet event (Carolyn Bessette-Kennedy famously did it too), but there’s a reason this look, which was unconventional at the time, became so memorable. The balancing of casual and couture that appeared in this look mixed wardrobe codes and was a way of doing red carpet style differently. It also had lasting appeal; see Zendaya’s 2022 Oscars look, a cropped white shirt and sequined bottom half that directly nodded to Stone.

1999 – Cate Blanchett

Cate Blanchett’s very first Oscars saw her dazzle with her take on ’90s simplicity, by way of John Galliano. The dress was backless and its floral details that scoop around the front and rear straps. A fitting, and memorable choice for your first Oscars if you’re Blanchett, who’s now a two-time winner.

1999 – Lil’ Kim

When you’re Lil’ Kim, you can wear anything. In the ’90s, the star became known just as much for her music as she was for her outré style and bold, energetic approach to fashion, something she bonded over with friends Marc Jacobs and the late Lee ‘Alexander’ McQueen. Outfits like this one, worn to the 1999 VMAs, may have incorrectly landed her on ‘worst-dressed’ lists, but the ‘How Many Licks’ rapper was every inch ahead of her time.