27 Iconic '90s Outfits That Will Go Down In Fashion History

In 1999, before Britney Spears was dubbed the “Princess of Pop,” she wore a playful outfit to the first-ever Teen Choice Awards in a baby pink tank and matching pants, equipped with metallic pink plates. Cue: “I’m Not A Girl, Not Yet A Woman.”

On the heels of her film Selena (pre-“Jenny From The Block”), Jennifer Lopez wore a cowl-neck chainmail crop top and a leather maxi at the 1998 MTV Movie Awards — her most underrated ‘fit ever.

This 1997 Princess Di outfit was iconic for two major reasons: One, it’s capital-S stunning. More importantly, she wore this too-spicy-for-regular-royals dress the very same night now-King Charles publicly confessed his infidelities, marking the official genesis of the “Revenge Dress.”

One of the most iconic fashion moments of the 1990s, Lil' Kim’s mermaid-inspired, one-shoulder look (complete with a shell-shaped nipple pasty) still goes hard — even in 2023.

The sheer dress may be ubiquitous now, but Kate Moss changed the see-through game in 1993 when she stepped out in an utterly diaphanous slip and exposed her contrasting black undies. Today, Olivia Wilde, Emily Ratajkowski, and Florence Pugh nod to this look all the time.

Julia Roberts has been known to rock oversized pantsuits on red carpets, yes. But the skirt suit she wore at the 1992 Golden Globes was especially chic. Paired with her perfectly messy bob, and gold hoops, she looked every bit the star.

TBH, I could see any of today’s style stars wearing Jada Pinket Smith’s shimmery, chainmail crop top and maxi skirt at the 1997 Oscars After Party. It’s a look worth copying, to be sure.

It’s already difficult to pull off micro bangs and a chevron print (one now stuck in “cheugy” purgatory) — together, even more so. But this ‘fit on Drew Barrymore just worked.

Before her infamous leg pop at the Oscars, there was this standout moment at a different award show: a spicy halter dress encrusted with crystals at the 1999 Golden Globes. She won a Best Performance by an Actress award, BTW.

Just your regularly-scheduled reminder that Beyoncé can do no wrong — in the fashion department or otherwise. She, Michelle Williams, and Kelly Rowland served all leather cut-outs in 1998. It was just one of many incredible (coordinating!) looks they’d serve during their tenure.

Gwyneth Paltrow was definitely a winner at the 1999 Oscars — as the recipient of the Best Actress award for her turn in Shakespeare in Love (and for slaying the red carpet in this blush pink ball gown).

Sarah Jessica Parker didn’t just take a page out of Carrie Bradshaw’s playbook, she took a whole dress out of her closet. After wearing the “naked dress” that caused much hoopla with Mr. Big in Season 1 of SATC, Parker wore the mini slip IRL to attend the VH1 Vogue Fashion Awards in 1997.

Let’s be real: the Spice Girls defined a style era in the ‘90s. But their appearance at the 1997 MTV VMAs — with platform sneakers, leopard prints, and athleisure staples to boot — was a total group slay.

There were almost too many Jennifer Aniston options to choose from, because she’s basically the IRL version of her ever-stylish on-screen persona, Rachel Green. But the Friends star may have been the most radiant in this sculpted brown number at the 1999 Emmy Awards. The glitzy ornate top, the smooth skirt, the messy hair? A vibe before vibes were called ‘vibes.’

Diane Keaton has been a style icon for decades, continually wowing with her takes on suiting. But this all-white ‘fit at the 1997 Academy Awards was beyond your usual realms of chic. With her styling touches — the glasses, the choker, gloves, and platform boots — she also made the look completely her.

Before Barbiecore, there was Audrey Hepburn. I have no words for this one-shoulder vibrant pink number the actress wore at the 1992 Oscars. Just wow.

Aaliyah had the best street style game, but no ‘fit ever eclipsed this white-hot look she served at the Anastasia premiere in 1997. With white sneaks, a faux fur coat, and her signature crop top, she looked wintry cool.

Cindy Crawford was a style icon of the 1990s and this saucy gown — for an Oscars date with Richard Gere, no less — is undeniably one of her best looks of the decade. Just fire.

Winona Ryder was all about grunge glam in the ‘90s. But she traded in her all-black ‘fits for an ivory, beaded, flapper-style number to attend the Academy Awards in 1994. With those pointed pumps? So good.

Diva history was made when Mariah Carey and Whitney Houston twinned at the 1998 MTV Video Music Awards. It was so iconic, in fact, that Dua Lipa and Meghan Thee Stallion paid homage to it by also wearing matching Versace looks to last year’s Grammys.

Let’s get this straight: Halle Berry can do no sartorial wrong. But this boudoir-inspired slip dress with sheer lace panels was probably her best effortlessly spicy look.

OK, but this metallic pink bandeau top and white pants ‘fit Britney Spears wore to perform at a 1999 concert is part of Spears’ fashion canon.

This white and gold number Kate Hudson wore to attend the 1999 MTV Movie Awards was equal parts angelic and daring — and utterly ‘90s.

Titanic’s Rose walked so Kate Winslet could run. She attended the 1998 Academy Awards in this regal gown, complete with a intricate embroidery reminiscent of her on-screen character’s elaborate wardrobe.

In 1991, Madonna channeled Marilyn Monroe in a glitzy strapless number and fur stole. She wore $20 million worth of Harry Winston bling, for a look that would be recreated for decades to come.

There’s something about Meg Ryan walking the red carpet in a fur-trimmed, zesty lime green coat that makes me wish I had a time machine...

Cameron Diaz served range in the ‘90s — donning everything from minimalist slips to preppy ‘fits. The saccharine vibes of the flutter sleeves and lone clip perfectly capture her then-status as a rom-com darling.

If you need proof that Nicole Kidman has always been a must-watch on the red carpet, here’s a delicately-embroidered chartreuse beauty to hold sway. Paired with a beaded bag, drop earrings, and pointed sky-blue slingbacks, this look was a gem.