With the 2024 Grammy Awards finally upon us, we’re looking back on the most shocking Grammys looks of all time.
While the Oscars may have the most glamorous red carpet displays, the Grammys are a night for fashion risk-takers to shine, resulting in some seriously crazy looks. From Jennifer Lopez’s plunging Versace dress to Nicki Minaj’s papal regalia, we’re taking a look back at the most shocking Grammys red carpet looks ever — until this year, that is.
Celebrities always tend to go all out for a red carpet, and by all out, we’re not talking the most beautiful dresses but looks that made our jaws drop. The Grammys are more about performance and creativity than the oh-so-formal-look-your-best approach, stars take the opportunity to push boundaries on this very special musical night.
They ask daring questions with their fashion choices, like: How much skin can I show before I am technically naked? And: What if an oyster turned into a dress?
As we look forward to the undoubtedly crazy looks this year’s Grammys red carpet will bring, we can’t help but be nostalgic for these red carpet looks of days gone by. Whether or not they stuck the landing, we love them for it. And we’ll never forget the things they’ve done in the name of fashion.
Ready for this ride down memory lane? Click through — you won’t regret it.
This story was originally published in January 2020.
-
Dawn Richard, 2024
Image Credit: Photo by Gilbert Flores/Billboard via Getty Images. Singer Dawn Richard wore one of the most daring looks of the night during the 2024 Grammys: a maroon gown with an elaborate leaf headdress.
-
Shania Twain, 2023
Image Credit: Lester Cohen/Getty Images for The Recording Academy Talk about Cruella de Vil! Shania Twain looked unrecognizable when she rocked this black and white sequined polka dot three-piece suit and matching hat to the 65th Grammy Awards.
-
Blac Chyna, 2023
Image Credit: Michael Buckner for Variety Giving some major Maleficent vibes, Blac Chyna arrived at the 65th Annual Grammy Awards in this black feathered number with an attached headpiece and gloves. Our thoughts go out to whoever had to sit behind her at during the show!
-
Lizzo, 2023
Image Credit: Michael Buckner for Variety Turning heads at the 65th Annual Grammy Awards, Lizzo wore this billowing bright red floral cape with a matching eye look.
It was a big year for the singer who took home the Record of the Year award for her hit, “About Damn Time.”
-
Lil Nas X, 2022
Image Credit: Brian Friedman/Variety/Penske Media via Getty Images Lil Nas X has changed the game when it comes to his red carpet fashion and we love this diamante look he wore in 2022.
-
Billie Eilish, 2022
Image Credit: Brian Friedman for Variety. Like always, Billie Eilish arrives in something many people have never seen before, including this oversized black ensemble with black sneakers.
-
Doja Cat, 2021
Image Credit: Kevin Mazur/Getty Images for The Recording Academy If looks could kill, Doja Cat’s fierce 2021 look would have wiped out the whole carpet! The singer went for a very revealing zipper dress with a feather bottom.
-
Dua Lipa, 2022
Image Credit: Brian Friedman/Variety/Penske Media via Getty Images Dua Lipa made everyone’s jaws drop when she arrived in this gown that’s giving us ‘90s Donatella Versace vibes. The strappy dress was accessorized with gold accents from top to bottom.
-
Phoebe Bridgers, 2021
Image Credit: Francis Specker/CBS ©2021 CBS Broadcasting, Inc. via Getty Images Phoebe Bridgers was unforgettable in this Thom Browne skeleton dress and dark lipstick to match her committed goth aesthetic.
-
Billy Porter, 2020
Image Credit: David Crotty/Patrick McMullan via Getty Images Pose star Billy Porter always kicks it up a notch for a red carpet event — and his 2020 Grammys look was no exception. That hat! Those boots!
-
Joy Villa, 2020
Image Credit: Axelle/Bauer-Griffin/FilmMagic via Getty Images Joy Villa ruffled more than a few feathers tonight when she showed up in a red, white, and blue “Trump 2020” Grammys gown.
She had previously worn a “Make America Great Again” gown in 2017.
-
Cardi B, 2019
Image Credit: Dan MacMedan/Getty Images Cardi B’s now-ex Offset could barely fit in frame when he posed for photos with the superstar in 2019
This Thierry Mugler creation made Cardi the pearl to its oyster, and is basically a walking version of Botticelli’s The Birth of Venus. In other words, this dress is art — full-stop.
-
Kylie Jenner, 2019
Image Credit: Dan MacMedan/Getty Images When Kylie Jenner supported then-boyfriend Travis Scott at the Gramys in 2019, her Balmain jumpsuit drew more than a few stares, and with good reason. Bare shoulders and a wide torso are topped off with attached — yes, attached! — matching gloves.
-
Pink, 2018
Image Credit: Max Parker/Everett Collection. Pink’s Armani Privé gown is giving us tie-dye ostrich vibes with a side of Muppets energy. She brought her kids to the show this year, so maybe they picked it out?
-
Lady Gaga, 2017
Image Credit: Axelle/Bauer-Griffin/FilmMagic via Getty Images Lady Gaga might be going for a more paired back fashion sense these days but she was once one of the most daring stars on the Grammys red carpet.
Her Alex Ulichny get-up in 2017 is one we won’t forget in a hurry — boobs out, platforms on, and ready to rock.
-
Katy Perry, 2017
Image Credit: Jon Kopaloff/FilmMagic via Getty Images Disco on top, feather duster on the bottom, sparkly streamers even further down??? Everything about Katy Perry‘s 2017 look, from the windswept lob to the mid-hip cutoff is very confusing to us.
-
Lady Gaga, 2016
Image Credit: Axelle/Bauer-Griffin/FilmMagic via Getty Images Lady Gaga’s 2016 Marc Jacobs dress looks like a robe that Dumbledore would have designed — in other words, no complaints there.
Paired with the foot-high platforms, neon orange hair, and blue eyeshadow, she definitely made it hard to look away!
-
Madonna, 2015
Image Credit: Jon Kopaloff/FilmMagic via Getty Images Madonna proved that she will always bring the shock-factor at the 2015 Grammys: This Givenchy ensemble features fishnets, over-the-knee boots, a lacy bullfighter-inspired bodysuit complete with epaulets, and long, fingerless gloves. Plus, whatever you’d call that hat-lace veil combination.
-
Rihanna, 2015
Image Credit: Jon Kopaloff/FilmMagic via Getty Images In a classic power move, Rihanna was the last one to show up at the 2015 Grammys red carpet. But even if she’d showed up on time, all eyes would have been on this sprawling Giambattista Valli dress.
-
Katy Perry, 2014
Image Credit: FilmMagic Katy Perry made sure we wouldn’t forget which award show she was at in 2014. The “Roar” singer wore a gauzy Valentino gown adorned with music notes. Cute!
-
Nicki Minaj, 2012
Image Credit: Dan MacMedan/WireImage via Getty Images All hail the…Pope? Nicki Minaj was a vision in Versace at the 2012 Grammys, and drove home the religious undertones (overtones?) by bringing a date in full Pope attire.
-
Lady Gaga, 2010
Image Credit: Dan MacMedan/WireImage via Getty Images While we were worried about Gaga breaking an ankle in those shoes, we loved this solar system-themed dress by Armani Prive. Her bright yellow hair is the perfect accent — the sun to her dress’s stars, if you will.
-
Cher, 2008
Image Credit: Vince Bucci/Getty Images Cher has never been one to play it safe. Silver beads that look like chain mail on top, patches of sheer and opaque mesh underneath, and a long satin skirt — we’re getting dizzy just looking at this Julia Gerard look.
-
Sheryl Crow, 2002
Image Credit: Gregg DeGuire/WireImage via Getty Images In a very 2002-themed moment, Sheryl Crow paired a teeny tiny lace-up romper with black cowboy boots and a furry duster.
-
Christina Aguilera, 2001
Image Credit: Kevin Winter/Getty Images Christina Aguilera made two interesting choices at the 2001 Grammys: multi-colored cornrows and a plunging lace-up Trish Somerville dress.
-
Toni Braxton, 2001
Image Credit: KMazur/WireImage via Getty Images Remember that boundary-pushing we were talking about? Yeah, Toni Braxton takes the cake, no question. Honestly, good for her — we’re sweating just thinking about wearing this Richard Tyler gown in public.
-
Jennifer Lopez, 2000
Image Credit: S. Granitz/WireImage via Getty Images What did we do to deserve Jennifer Lopez? This iconic Versace dress from 2000 enjoyed a revival in 2019, when Lopez wore a reimagination of the dress at Milan Fashion Week. But will anything ever truly top the original, or the frenzy it inspired? We think not.
-
Will Smith, 1999
Image Credit: Kevin Mazur/WireImage via Getty Images Okay, Will Smith! He walked out of the Grammys with an award for his performance of “Gettin’ Jiggy Wit It” — and walked in in a very confusing full leather suit.
-
Jada Pinkett Smith, 1999
Image Credit: Ron Galella, Ltd./Ron Galella Collection via Getty Images Jada Pinkett Smith complemented husband Will’s ensemble with a gold cut-out dress and an early peek at a 2000s trend: lace-up gladiator sandals that tied up to the knee.
-
Mary J Blige, 1996
Image Credit: Steve Granitz/WireImage via Getty Images Mary J. Blige cat-like ensemble in 1996 drew a few stares: from the head-to-toe leopard to the black shades and gloves, you may not have understood it — but you had to respect it.
More Stories from Entertainment
Leave a Comment