Looking Back: 20 Years of Oscar Fashions

During Oscar season, it's always fun to look back at some of the highs and lows in the history of Hollywood's biggest night. Not a lot of people can quickly recall who the winners were, and even fewer could name the nominees who didn't take home the prize. But it's a safe bet to say that everyone's got some red carpet favorites they won't quickly forget. It's hard to omit some of the great moments belonging to the likes of Cher, Julia Roberts, and Halle Berry, but they were more than 20 years ago. We're limiting our retrospective of memorable Oscar red carpet looks to the past 20 years. And they're not being labeled best or worst. Instead let's call them red carpet looks we won't soon forget.

In 2022, Will Smith and Jada Pinkett Smith only had to show up for a pretty much guaranteed ascension into the inner circle of the inner circle of Hollywood legends. And they showed up looking the part: Jada in an emerald green couture collaboration between Jean Paul Gaultier and Glenn Martens of Diesel and Y/Project; Will in a classic black Dolce & Gabbana tux and Cartier accessories. We all know what happened next. Even if she wanted to make a quick exit, Jada was going nowhere in a hurry with that enormous train. Apparently, the incredible dress was heavy and stiff on a night she really could've used something a little more comfortable.

Now that we've gotten Oscar's most glamorous and notorious couple out of the way, let's take a look back at some of the most memorable red carpet moments of the last 20 years.

Timothée Chalamet got plenty of attention on the carpet in 2022 where he continued to push the envelope in Louis Vuitton. The young actor wore black tapered pants, Chelsea boots, and a black lace and sequined tuxedo jacket. And the piece de resistance: no shirt – definitely an Oscar first.

In 2020, Brad Pitt picked up his statue for "Once Upon a Time...in Hollywood" in a classic black tux by Brioni. It's Brad Pitt – he always looks good. And on one of the biggest nights of this bona fide movie star's life, he looked better than ever. That's how a star does it

A little black Atelier Versace gown with a thigh-high split, amazing gams, bright red lipstick, and an uncanny ability to work it, is all it took for Angelina Jolie to become a wildly popular meme in 2012. The former Mrs. Pitt made quite a statement the night she became an Oscar fashion icon. Damn, that was a moment.

In 2019, Rami Malek chose a classic black three-piece custom St. Laurent tux to claim his prize for his turn as Freddie Mercury in "Bohemian Rhapsody." Throughout the evening his bow-tie was crooked, and despite futile attempts by the likes of Lady Gaga and his girlfriend, Lucy Boynton, it didn't get straightened out until he made his way backstage to the press room.

Also in 2019, Billy Porter made Oscar fashion history for his fabulous outfit. From the waist up, he was the epitome of the well-dressed Oscar attendee in a black velvet jacket, a white shirt with ruffles, and a bow tie that was unconventional for this carpet, but certainly nothing to cause heads to turn. From the waist down, however, his Christian Siriano gown shattered all conventions at the Academy Awards. Way to shake up the status quo, Billy Porter.

In 2014, fledgling actress Lupita Nyong'o ruled the red carpet throughout the entire awards season. By the time the Oscars rolled around she was at the top of every best-dressed list in the business. But it all paled by comparison when she picked up her Oscar for "12 Years a Slave" in a breathtaking baby blue Prada gown and a Fred Leighton diamond headband. Talk about real-life Cinderella moment.

Jennifer Lawrence showed up and turned heads at the Oscars as a first-time nominee in a sexy, red Calvin Klein dress. Two years later, at the 2013 ceremony, she was an odds-on-favorite to take home the Best Actress trophy for "Silver Linings Playbook." She looked like a beautiful young princess in a pale pink strapless gown with a voluminous skirt that proved to be her downfall on the way up the stairs to claim her trophy. Even laying on the stairs she exuded elegance. Of course she was wearing a 74-carat diamond necklace backwards. She shone from every angle.

The late, great, legend Prince presented the award for Best Song in 2005 wearing a purple (of course) velvet tuxedo japcket with a white pocket square, white open-collared shirt, and white wide-legged pants. This look is timeless on Prince and is definitely one of the all-time best Oscar looks. Purple perfection.

Sandra Bullock showed up in 2010 in a custom gold Marchesa gown designed by Georgina Chapman and Keren Craig. The only thing missing from the glamorous outfit was Oscar gold, which she picked up later that night for her performance in "The Blind Side."

The most nominated actor of all time, Meryl Streep, also had luck wearing gold. In custom Lanvin with a plunging neckline and a draped train, the legendary actress took home her third Oscar for her turn as Margaret Thatcher in "Iron Lady" in 2012.

With her seventh nomination looking like a possible win, Glenn Close went to the 2019 Oscars in an all gold Wes Gordon for the House of Herrera gown that sparkled more than any trophy in the room. Though she didn't win for her critically acclaimed performance in "The Wife," the actress went home with a 42-pound gold dress made from 4-million beads. Oscar is fickle. Fingers crossed, Glenn. There will be others.

Chadwick Boseman blew up Twitter when he stormed the 2018 red carpet in Givenchy Haute Couture. The long black coat with the silver detailing, the tapered pants, pointy boots, and David Yurman jewelry made this one of the most memorable red carpet looks of all time.

Charlize Theron was a relatively unknown South African actress when she walked her first red carpet as an Oscar nominee in 2004. By the time she picked up the trophy, everyone knew her name. The stunning blonde brought old Hollywood glamour to the party. The backless, beaded Dior dress flattered her incredible body and began a long-time love affair between Theron and fashionistas everywhere. When she steps on that carpet, she is flawless. That's a movie star!

Jared Leto made every best dressed list in 2014 with his impeccably tailored white Saint Laurent jacket, red bow tie and coordinating pocket square. It was a great look for the fashion forward long-haired actor who took home a trophy that night for "Dallas Buyers Club."

Gwyneth Paltrow always takes risks on the red carpet and hardly ever misses. One of her finest moments was in 2012 when she nearly stopped traffic on the red carpet in a white Tom Ford cape dress. With minimal makeup, a casual ponytail, and only a diamond cuff for jewelry, the Oscar-winning actress brought relaxed chic to both her and Tom Ford's finest red carpet moment to date.

Nominee Viggo Mortensen stood out on the 2008 red carpet with an evening coat with a red rose boutonniere over his tux. Sophistication with a bit of a rugged edge courtesy of his heavy beard.

Octavia Spencer made all the 2012 best-dressed lists in custom Tadashi Shoji designs. When she picked up her Oscar for Best Supporting Actress in "The Help," the actress wore a beaded, cream-colored gown that beautifully flattered her figure. It was the perfect dress for the perfect evening for the beautiful, talented actress.

Hilary Swank turned more than a few heads in a backless navy Guy Laroche gown when she walked the carpet on her way to picking up her second Oscar in 2005. The "Million Dollar Baby" star stunned in the long-sleeved, high-necked dress that looked like an impeccably fitting conservative dress – until she walked away.

Questlove proved that you don't have to go the classic tux route in order to make some kind of best- or worst-dressed list on Oscar night. In 2021, he wore Crocs on the carpet and into the Oscar ceremony. It didn't really matter what else he wore. The Crocs were gold and they were amazing.

Three-time Oscar winner Frances McDormand opted for custom Valentino when she presented an Oscar in 2019. It wasn't the dress or her usual choice of no makeup that caught everyone's attention. It was the custom yellow suede Birkenstocks that only she could rock at one of the most glamorous events in the world.

Lately, the Oscar fashions have been more safe than fun. Enough with the typical Hollywood glam squad creations. We need someone with a bit of an edge to give us something to talk about on March 10th. Whether it's good or bad, wearing something people will remember long after the show is over is always good business. Who's it going to be?