The Most Daring Grammy Awards Fashion Looks of All Time

Jennifer Lopez, Lady Gaga, Nicki Minaj and Lil Kim are just some of the stars who have turned heads on the Grammy Awards red carpet with their eclectic looks.

By Corinne Heller Jan 21, 2020 11:00 AMTags

When it comes to daring fashion, can anyone top J.Lo this year at the 2020 Grammy Awards?

Jennifer Lopez famously wore a green plunging Versace gown to the 2000 ceremony, and it was even more risqué for its time. The singer and actress last year recreated the look, wearing an even sexier version of it—no really—at one of the designer's fashion shows and looked better than ever.

Lady GagaMadonnaCardi BNicki Minaj and Lil Kim are more stars who have turned heads on the Grammy Awards red carpet with their eclectic looks. While the stars are both known for her wild styles, and there was one year in particular where Gaga hatched up quite the fashion plan and entrance!

Gaga is expected to attend the 2020 Grammys, as she is nominated for three awards for her music in the hit remake A Star Is Born. Madonna is also nominated for an award, for Best Remixed Recording, and Cardi and husband Offset received a nod for their track "Clout."

Grammys 2020: Snubs and Surprises

Check out the most daring Grammy looks of all time:

Jennifer Lopez

But the queen of Grammys fashion has to be J.Lo, who wowed in this daring green Versace gown to the 2000 Grammys. In 2019, she wore an updated version of the now-iconic dress at the brand's runway show during Milan Fashion Week, and later while hosting SNL.


The OG Queen of Pop left no daring fashion behind at the 2015 Grammys.

Lady Gaga

The singer always makes a statement with her red carpet looks, but this one was particularly unique: She arrived at the 2011 Grammys...inside an egg.

Cardi B

The rapper showcased Sandro Botticelli "The Birth of Venus" vibes with the Thierry Mugler 1995 Fall Couture gown she wore to the 2019 Grammys.

CeeLo Green

The singer brought out his golden alter ego Gnarly Davidson for the 2017 Grammys.

Annie Lennox

The singer attended the 1995 Minnie Mouse.

Nicki Minaj

The hip-hop star made a religious statement at the 2012 Grammys.

Lil Kim

It's no purple nipple cover, but the artist did turn heads at the 2002 Grammys with this red hot look.

The 2020 Grammy Awards will air live from Staples Center in Los Angeles on CBS on Sunday, January 26 at 5 p.m. PT / 8 p.m. ET.

Check out a full list of Grammy nominations.

Watch E!'s Live From the Red Carpet 2020 Grammy Awards coverage Monday, 27th Jan. starting at 8am. Catch the repeat show later that night at 6:30pm only on E!