Wildest Grammys Dresses Of All-Time: Billie Eilish & More

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February 4, 2023 9:00AM EST

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!

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Wackiest Grammys Dresses Ever: Photos

Wackiest Grammys Dresses Ever: Photos — 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.

With that in mind, there has been no shortage of jaw-dropping looks at the Grammys through the years. Take Katy Perry at the 2011 awards. The ‘Firework’ songstress looked heaven-sent as she rocks a sequined bra with a wrap skirt and angel wings to music’s biggest night.

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

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Lizzo — 2023

Lizzo — 2023 — 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.

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Billie Eilish — 2022

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

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Carrie Underwood — 2022

Carrie Underwood — 2022 — 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.

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SZA — 2022

SZA — 2022 — 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.

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Cardi B — 2019

Cardi B — 2019 — 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.

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Doja Cat — 2021

Doja Cat — 2021 — 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.

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Alicia Keys In 2004

Alicia Keys In 2004 — 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.

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Sheryl Crow — 2002

Sheryl Crow — 2002 — 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.

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Christina Aguilera — 2004

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

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CeeLo Green — 2017

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

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Madonna — 2017

Madonna — 2017 — 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.

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Maddie Ziegler & Sia — 2015

Maddie Ziegler & Sia — 2015 — 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.

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Rihanna In 2015

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

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Lady Gaga In 2016

Lady Gaga In 2016 — 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.

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M.I.A. In 2009

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

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M.I.A After Her 2009 Performance

M.I.A After Her 2009 Performance — 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.

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Lady Gaga In 2017

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

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Lady Gaga In 2010

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

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Lady Gaga In 2011

Lady Gaga In 2011 — 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.

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Nicki Minaj In 2012

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

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Girl Crush

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

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Nicki Minaj In 2011

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

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Katy Perry In 2017

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

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Alicia Keys In 2012

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

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Janelle Monae

Janelle Monae — 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.

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Rihanna In 2011

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

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Missy Elliot

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

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