'90s Awards Show Outfits We're Still Thinking About

While each decade has its distinct fashion, we can all agree that the '90s showed the perfect balance of edginess and sophistication, plenty of authenticity paired with bold trends, and most of all, a collective willingness to push boundaries and set new fashion norms. And what better place to see all of the above than at the many award show red carpets? From the glamorous and unpredictable looks that A-listers gave us at the Academy Awards to the quirky pieces they wore to the MTV Video Music Awards, the '90s had plenty of stellar outfit moments.

During this decade, many up-and-coming stars explored what direction their style should take. At the same time, established divas experimented with how far they could push their red carpet looks. The '90s were truly a great time to have fun with style, and Hollywood knew it. Its most prominent stars had no problem going whimsical about it. But let's not spoil too much ahead, as these photos of the award show red carpet fashion from the '90s speak for themselves!

In 1997, Jennifer Lopez was still an up-and-comer, but the moment she showed up at the Academy Awards, all eyes were on her. At the time, Lopez was in the spotlight thanks to the biographical drama "Selena." For the prestigious award show, she opted for an intricate, retro-looking dress by Badgley Mischka, featuring detailed embroidery and sequins. The soon-to-be pop star paired the fit with retro side-swept curls and glamorous makeup, both of which helped round off the look. Since her breakthrough, Jennifer Lopez's style transformation has been head-turning. 

Julia Roberts has always been a trailblazer, and her fashion choices have pushed boundaries. In 1990, the star, then best known for her performance in "Steel Magnolias," showed up at the Golden Globes in a slightly oversized gray men's pantsuit by Armani. The look was androgynous and unexpected, showing that dresses don't have to be the norm. "I could not have known that it was going to become this, like, statement outfit. I just thought I looked fabulous, and I still have that suit," she explained to Vogue in 2024.

Princess Diana's revenge dress became one of the most iconic looks in fashion history, but other revenge dresses also gave us incredible fashion moments in the '90s. More specifically, in 1997, pop star Mariah Carey showed up to the MTV Video Music Awards donning a simple yet revealing black number consisting of a tiny bandana top and a maxi skirt with a thigh-high slit. This dress remains one of the "Fantasy" singer's best revenge fashion moments, as she wore it after separating from her then-husband, businessman Tommy Mottola. 

By the late '90s, Cher was well known for her bold fashion choices, so when she showed up at the Academy Awards in 1998, her Bob Mackie dress wasn't all that shocking. However, the combination of the extravagant hat and sheer beige dress remains one of her most daring fashion looks. Ironically, the "Strong Enough" singer revealed that this dress wasn't her favorite look. "I liked the hat and had all kinds of time to tell Bob I didn't really like the dress," she said (via Vogue).

Actor Halle Berry, who was best known for films like "Boomerang" and "Losing Isaiah" at the time, looked absolutely stunning at the 1996 Academy Awards. For the big night, Berry wore a delicate lavender-purple Valentino gown, and the color (which we don't see too often at fancy red carpet events) suited her beautifully. The dress — which featured flower-embellished straps, chiffon and satin layers, and a shawl around Berry's neck — remains a great example of how fun and whimsical '90s red carpet fashion was. Needless to say, this was only the beginning of Halle Berry's stunning style transformation.

In 1999, breakout star Christina Aguilera walked the red carpet at the MTV Video Music Awards in a leopard-print look that defined the trends of the upcoming decade. For this award show red carpet, the "What a Girl Wants" singer wore a black mini skirt with black knee-high boots paired with a sheer leopard print top and leopard print jacket. The look was maximalist and fun. The pink details, as well as Aguilera's jewelry, makeup, and hair, certainly gave us a glimpse of where fashion and beauty were heading in the early aughts.

Walking hand in hand with Hollywood heartthrob and then-boyfriend Brad Pitt, Jennifer Aniston stunned on the 1999 Emmys red carpet. The "Friends" actor perfectly balanced award-show chic with her trademark casual cool-girl aesthetic by wearing a semi-sheer sequin halter top and a brown maxi skirt gown by Randolph Duke. While Aniston's fashion was perfection, her messy boho curls were a choice that she probably could have lived without.

While sheer dresses are much more common today, back in the '90s, it was only the ultra-cool girlies who even dared to explore the trend for red carpet award shows. In 1998, actor Rose McGowan, known for films like "Scream" and "Going All the Way," showed up to the MTV Video Music Awards in a completely sheer chainmail dress designed by Maja Hanson. "That was my first public appearance after being sexually assaulted. I was like, 'Is this what you want?'" she revealed in 2018 on the Dr. Oz Show (via Yahoo!). "That was a political statement."

In 1999, singer Céline Dion showed up to the Academy Awards in a white tuxedo by John Galiano. While wearing a pantsuit to an award show as a woman was unusual in itself at the time, Dion took things even further. The "My Heart Will Go On" singer opted to wear the tux backward, creating a stunning backless moment. "I was the only one with pants in a backward suit from Galliano and if I would do this today it would work," she told People in 2017. "It was avant-garde at the time."

The 1999 Oscars were flooded with memorable fashion moments, and Gwyneth Paltrow's pink Ralph Lauren gown is certainly among them. The spaghetti-strap dress featured a tight bodice and a flowy A-line skirt. The "Shakespeare in Love" star paired it with a matching sheer shawl and choker necklace. The dress was famously inspired by beauty and fashion icon Grace Kelly's style, and Paltrow definitely looked like Hollywood royalty in it.