Search

NewsExpand Menu

EntertainmentExpand Menu

BeautyExpand Menu

FashionExpand Menu

ShoppingExpand Menu

TrendingExpand Menu

Celebrity BiosExpand Menu

Wildest Grammys Dresses of All-Time: See Photos of the Craziest Fashion

By:
February 1, 2026 4:00PM EST
Wildest Grammys Dresses of All-Time: See Photos of the Craziest Fashion Lizzo
FilmMagic

Some of our favorite stars have made bold moves by wearing quite crazy dresses to the Grammy Awards over the years. See the wackiest pics here!

Every year, the Grammys dare artists to take a risk on the red carpet. As the biggest night in music, creativity reigns supreme and that ethos applies to the fashion just as much as the beats. Grammy-perfect outfits range from over-the-top sparkles, to barely-there pieces or looks that are basically costumes. Anything eye-catching is a win!

Hair and makeup are just one more avenue for stars to get weird! Bright wigs, wild lipstick, and edgy eye makeup will surely help the VIP set stand out.

Want to see more of the most daring Grammy looks over the years? Scroll through our gallery for the wildest, most outrageous outfits.

1 of 28

Lizzo — 2023

Lizzo — 2023
David Fisher/Shutterstock

Lizzo wore a jaw-dropping ensemble for the 2023 Grammys. The singer wrapped herself in red Dolce & Gabbana blooms with a sexy orange dress underneath.

February 6, 2023, 8:49AM
2 of 28

Billie Eilish — 2022

Billie Eilish — 2022
Matt Baron/Shutterstock

Billie Eilish rocks a black Rick Owens ensemble to the 2022 Grammys. The oversize caped coat was paired with a black dress and sunglasses.

February 2, 2023, 8:47AM
3 of 28

Carrie Underwood — 2022

Carrie Underwood — 2022
David Fisher/Shutterstock

Carrie Underwood looked stunning at the 2022 Grammys, but her dress made quite a statement! The two-toned ensemble featured a sparkling bodice leading into a poofy skirt.

February 2, 2023, 8:47AM
4 of 28

SZA — 2022

SZA — 2022
Broadimage/Shutterstock

SZA rocked a sheer dress to the 2022 Grammy Awards, which was adorned with a floral design down the center. The dress also featured a long sheer train.

February 2, 2023, 8:47AM
5 of 28

Cardi B — 2019

Cardi B — 2019
Chelsea Lauren/Shutterstock

To shell and back! Cardi B looks like a Bottocelli in this Mugler number she wore to the 61st Annual Grammy Awards on Feb. 10, 2019.

March 30, 2022, 4:11PM
6 of 28

Doja Cat — 2021

Doja Cat — 2021
Jay L Clendenin/Los Angeles Time

Ruffling feathers. Doja Cat takes the plunge in Roberto Cavalli on the red carpet at the 63rd Annual Grammy Awards on Mar. 14, 2021. Short bangs and a wild, feathered lime green skirt made for an edgy ensemble.

March 30, 2022, 4:12PM
7 of 28

Alicia Keys In 2004

Alicia Keys In 2004
KRT/Newscom/MEGA

Go with the flow! Alicia Keys arrives for the 46th Annual Grammy Awards on Feb. 8, 2004 wearing white jeans with a two-toned blouse with a train.

March 30, 2022, 4:12PM
8 of 28

Sheryl Crow — 2002

Sheryl Crow — 2002
Mark J Terrill/AP/Shutterstock

Look, all she wants to do is have some fun. Sheryl Crow arrives at the 44th annual Grammy Awards in 2002 wearing a tiny lace-up romper and a long patchwork coat with sunglasses.

March 30, 2022, 4:12PM
9 of 28

Christina Aguilera — 2004

Christina Aguilera — 2004
Dan Steinberg/BEI/Shutterstock

Christina Aguilera flaunts her fringe appeal at the 2004 Grammys. Her modern flapper look was teamed with dark, finger-waved locks.

March 30, 2022, 4:12PM
10 of 28

CeeLo Green — 2017

CeeLo Green — 2017
Jim Smeal/REX/Shutterstock

Heavy metal! CeeLo Green covers himself in a gold dress and matching mask at the 2017 Grammy Awards. 

February 7, 2019, 1:12PM
11 of 28

Madonna — 2017

Madonna — 2017
Jim Smeal/BEI/REX/Shutterstock

No shortage of texture here. Madonna’s look at the 2017 Grammys was OUT there, and featured fishnet stockings and a complicated bustier-style ensemble.

February 7, 2019, 1:13PM
12 of 28

Maddie Ziegler & Sia — 2015

Maddie Ziegler & Sia — 2015
Jim Smeal/BEI/REX/Shutterstock

Maddie Ziegler and Sia Furler match in wigs and suits at the Grammys in 2015. In their defense, it went with the aesthetic of their performance.

February 7, 2019, 1:12PM
13 of 28

Rihanna In 2015

Rihanna In 2015
Picture Perfect/REX/Shutterstock

Rihanna rocks a pink dress with an insanely poofy skirt at the Grammys in 2015.

February 7, 2019, 1:12PM
14 of 28

Lady Gaga In 2016

Lady Gaga In 2016
Jim Smeal/REX/Shutterstock

Lady Gaga rocks massive heels, a printed dress, red wig and blue eye makeup to the 2016 Grammys. However, we’ll give her a pass on the out-there look, as she was paying tribute to David Bowie.

February 7, 2019, 1:12PM
15 of 28

M.I.A. In 2009

M.I.A. In 2009
Picture Perfect/REX/Shutterstock

M.I.A rocks a poofy blue dress and sneakers on the Grammys red carpet in 2009.

February 7, 2019, 1:12PM
16 of 28

M.I.A After Her 2009 Performance

M.I.A After Her 2009 Performance
Jim Smeal/BEI/REX/Shutterstock

Dot’s how you do it! While pregnant at the Grammys in 2009, M.I.A wore a completely sheer ensemble and put her baby bump front and center in the press room.

February 7, 2019, 1:12PM
17 of 28

Lady Gaga In 2017

Lady Gaga In 2017
Broadimage/REX/Shutterstock

Peek-a-boob! Lady Gaga’s top barely covers her chest and midsection in this wild look from the 2017 Grammys.

February 7, 2019, 1:12PM
18 of 28

Lady Gaga In 2010

Lady Gaga In 2010
REX/Shutterstock

At the 2010 Grammys, Lady Gaga went all out in this insane wire dress, complete with massive hand garnish. Her yellow locks looked divine.

January 25, 2018, 2:47PM
19 of 28

Lady Gaga In 2011

Lady Gaga In 2011
Shutterstock

No yolk, Lady Gaga knows how to make an entrace. She arrived at the 2011 Grammts inside of an egg, carried by a crew of people.

January 25, 2018, 2:41PM
20 of 28

Nicki Minaj In 2012

Nicki Minaj In 2012
REX/Shutterstock

Very Versace! Nicki Minaj’s red frock at the 2012 Grammys was interesting to say the least.

January 25, 2018, 2:41PM
21 of 28

Girl Crush

Girl Crush
REX/Shutterstock

Ball pit chic? Girl Crush is a human ball pit in this colorful look in 2017.

January 25, 2018, 2:41PM
22 of 28

Nicki Minaj In 2011

Nicki Minaj In 2011
REX/Shutterstock

Nicki Minaj wears a wacky leopard-print outfit to the 2011 Grammys.

January 25, 2018, 2:41PM
23 of 28

Katy Perry In 2017

Katy Perry In 2017
REX/Shutterstock

It looks like the top and bottom of Katy Perry’s 2017 Grammys dress didnt quite communicate! At least her hair looks good!

January 25, 2018, 2:41PM
24 of 28

Alicia Keys In 2012

Alicia Keys In 2012
REX/Shutterstock

Mix and match! In 2012, Alicia Keys wore a pair of floral-print jeans under her teal wrap dress with a headwrap.

January 25, 2018, 2:41PM
25 of 28

Janelle Monae

Janelle Monae
REX/Shutterstock

Not to pop her bubble, but this circular skirt Janelle Monae wore at the 2016 Grammys was a bit eccentric. No matter, Janelle loves pushing boundaries.

January 25, 2018, 2:41PM
26 of 28

Katy Perry — 2011

Katy Perry — 2011
Broadimage/REX/Shutterstock

Katy Perry looked heaven-sent at the 2011 awards as she rocked a sequined bra with a wrap skirt and angel wings to music’s biggest night.

February 7, 2019, 1:12PM
27 of 28

Rihanna In 2011

Rihanna In 2011
REX/Shutterstock

On cloud 9! Rihanna always looks incredible at the 2011 Grammys, but this sheer and ruffled ensemble was definitely OUT there!

January 25, 2018, 2:41PM
28 of 28

Missy Elliot

Missy Elliot
REX/Shutterstock

Packing the punch in purple! Missy Elliott’s 2002 Grammys look was VERY in-your-face!

January 25, 2018, 2:41PM