Most Shocking Oscars Looks Through the Years

Of all the events in Hollywood, the Academy Awards is home to some of the most over-the-top and flamboyant looks of all time. It’s basically the mother of all award shows, and each year our favorite celebs hit the red carpet in jaw-dropping couture that leaves us absolutely floored. Sunday, March 12, marks the 95th Oscars ceremony, and we can’t wait to see our favorite A-listers serving some serious looks. With a rich history of shocking looks from Lady Gaga’s red gloves to Björk’s swan dress, the Oscars are pretty much a guarantee for a memorable set of looks.

Following suit with this year’s awards shows, we’re expecting the ceremony to send off this awards season with a total bang. In that spirit, we’re taking a look back at some of the most outrageous red carpet looks through the years — the good, the bad, and the huh? — and there are fashion highs and lows we’ll never forget, from Angelina Jolie’s high-slit Versace gown to Cher’s, well, everything.

See all the looks that drew stares below, some that raised the bar for fashion, and others we still just don’t get.

A version of this article was originally published in April 2021.

Cara Delevingne

Image Credit: Kayla Oaddams/WireImage

Cara Delevingne arrived at the 95th Annual Academy Awards wearing this cherry red gown from Elie Saab and it is by far one of the most breathtaking fashion moments we’ve seen this year — and possibly any year?
Allison Williams

Image Credit: Kevin Mazur/Getty Images

Allison Williams did not come to play in this showstopping blush pink gown from Giambattista Valli. The dramatic train has won over our hearts, along with the Old Hollywood-style sequined dress.
Mindy Kaling

Image Credit: Kevin Mazur/Getty Images

Mindy Kaling took our breath away in one of her most daring red carpet ensembles at the Oscars 2023, rocking a custom Vera Wang dress with stunning cutouts.
Timothée Chalamet

Image Credit: Gilbert Flores for Variety.

Dune star Timothée Chalamet’s shirtless look (and occasional tendency to flip off the camera) certainly caught viewers’ attention on the 2022 Oscars red carpet.
Kristen Stewart

Image Credit: Jeff Kravitz/FilmMagic

Kristen Stewart made everyone hav a double-take at the 2022 Oscars red carpet as she wore these black mini shorts, an unbuttoned white button-down and a black blazer on top.
Barbra Streisand

Image Credit: AP.

Funny girl, indeed. Barbra Streisand’s peter pan collar and sheer pantsuit left people scratching their heads at the 1969 Oscars.
Cher

Image Credit: WWD.

Cher has turning heads at the Oscars since 1974, when this less-is-more pastel look made fashion headlines.
Cher

Image Credit: ASSOCIATED PRESS.

Cher’s attire at the 1986 Academy Awards can only be described as daring from head to toe. When the wig is bigger than the rest of the outfit, that’s really saying something.
Demi Moore

Image Credit: Ralph Dominguez/MediaPunch/IPX.

Demi Moore went where so few women have gone before at the 1989 Oscars: bike shorts on the red carpet. And you know what? She still kinda rocks it.
Kim Basinger

Image Credit: Ralph Dominguez/MediaPunch/IPX.

Kim Basinger, mom of lookalike daughter Ireland Baldwin, made a splash at the 1990 Academy Awards in this one-shoulder dress.
Whoopi Goldberg

Image Credit: ASSOCIATED PRESS.

Whoopi Goldberg’s dress was full of surprises in 1993 (there are pants under there!), and we’re also pretty sure this was the inspiration for Princess Fiona in Shrek.
Kate Hudson

Image Credit: ASSOCIATED PRESS.

While Kate Hudson hasn’t aged a day since this pic from the 2001 Oscars, we think her style has definitely evolved from this high-collared look.
Björk

Image Credit: AP.

The infamous swan dress made history in 2001 when Björk walked out in the Marjan Pejoski number that had all eyes on her.
Gwyneth Paltrow

Image Credit: Star Max via AP Images.

Gwyneth Paltrow’s eyeliner at the 2002 Oscars would have made Avril Lavigne proud, but the actress’ severe look wasn’t met with high praise at the time.
Uma Thurman

Image Credit: AP.

Part German milkmaid, part Sumo wrestler, Uma Thurman’s 2004 Oscars look never quite makes up its mind — even the hemline can’t pick a side.
Hilary Swank

Image Credit: ASSOCIATED PRESS.

Hilary Swank was a million-dollar lady at the 2005 Academy Awards in a backless gown that left her fans swooning.
Tilda Swinton

Image Credit: AP.

We love Tilda Swinton, but she’s bringing us down in this shapeless velvet look from the 2008 show.
Madonna

Image Credit: Evan Agostini via AP.

Madonna is no stranger to shocking the cameras on a red carpet, but her 2010 look was double trouble — thigh-high slits and lace, plus the appearance of then 14-year-old daughter Lourdes Leon.
Angelina Jolie

Image Credit: Lindensmith/McMullan/Sipa Press.

While this wasn’t the first Oscars ceremony Angelina Jolie attended with ex Brad Pitt, it may have been the one that cemented them as power couple Brangelina — and this slit definitely made that happen in 2012.
Lady Gaga

Image Credit: Jordan Strauss/Invision/AP.

Lady Gaga’s 2015 Oscars look was almost a perfect 10 — minus some giant red gloves that looked more Mr. Clean than movie star glam.
Paris Jackson

Image Credit: Evan Agostini/Invision/AP.

Daughter of Michael Jackson Paris Jackson left little to the imagination when it came to her love of tattoos at the 2018 Oscars party, and her bejeweled, inked-up look drew plenty of stares.
Taraji P. Henson

Image Credit: Jordan Strauss/Invision/AP.

Angelina who? Taraji P. Henson reinvented the slit at the 2018 Academy Awards and let her legs do the talking.
Rita Moreno

Image Credit: Elizabeth Goodenough/Everett Collection.

Rita Moreno proves that being an outfit repeater pays off at the 2018 Oscars, stunning in the same dress she first wore to the Oscars in 1962.
Billy Porter

Image Credit: Richard Shotwell/Invision/AP.

Billy Porter’s 2019 Oscars look was the best of both worlds and the absolute definition of formalwear.
Laura Dern

Image Credit: ©AMPAS / Courtesy Everett Collection.

2020 Oscar-winner Laura Dern took the 2021 Oscars red carpet in this dress featuring voluminous feathers on the skirt and a long sleeve black top.
Gwyneth Paltrow

Image Credit: Kevin Mazur Archive/WireImage

At the 1999 Oscars, Gwyneth Paltrow absolutely wowed in this baby pink billowing gown and matching tulle shawl. The actress went on to win the Best Actress award for her leading role in Shakespeare in Love.
H.E.R.

Image Credit: ABC via Getty Images

In the 2021 Oscars, H.E.R. won her first Oscar for her song “Fight for You” in Judas and the Black Messiah. For the big event, she wore this showstopping bright purple bedazzled jumpsuit with a cape detail. So stunning!
Halle Berry

Image Credit: Steve Granitz/WireImage

Speaking of winners’ looks, Halle Berry wore this iconic dress when she won her Best Actress Award for her role in Monster’s Ball in 2002. Berry, who became the first woman of color to win in the category, dared in this sheer dress with floral appliqués and a billowing maroon skirt.
Zoë Saldana

Image Credit: Bob Riha, Jr./Getty Images

Actress Zoë Saldana wore this showstopping dégradé Givenchy gown to the 2010 Oscars. What a statement!