These Are The Best Grammys Looks Of All Time

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Eliza Huber
·4 min read
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Style-wise, the Grammys stand out from the rest of the award shows. Whereas Hollywood’s finest like to play it safe at the Oscars and the Golden Globes, choosing pretty gowns and the occasional suit, those who attend music’s biggest night of the year rarely follow suit, with grandiose entrances and outfit changes a common occurrence. That’s how we ended up with such a wide array of daring looks from Grammys past, including J.Lo’s iconic Versace jungle gown, Cardi B’s Mugler oyster masterpiece, and Rihanna’s bubblegum pink Giambattista Valli meme dress.

With the 63rd Annual Grammy Awards airing on Sunday sans the extravagant red carpet we’ve grown accustomed to over the years, we thought we’d take a trip down memory lane. Ahead of Sunday night’s festivities, join in as we count off our all-time best-dressed looks from the days when red carpets didn’t take place primarily on Instagram.

<h2>Megan Thee Stallion, 2021</h2><br>Megan Thee Stallion didn't just win Best New Artist at the 2021 Grammys — she won Best Dressed, too. <span class="copyright">Photo: Kevin Mazur/Getty Images.</span>

Megan Thee Stallion, 2021


Megan Thee Stallion didn't just win Best New Artist at the 2021 Grammys — she won Best Dressed, too. Photo: Kevin Mazur/Getty Images.
<h2>Ariana Grande, 2020</h2><br>"Baby, you can shut up" if you don't like this 20-foot, custom Giambattista Valli gown on Ariana Grande. <span class="copyright">Photo: Steve Granitz/WireImage.</span>

Ariana Grande, 2020


"Baby, you can shut up" if you don't like this 20-foot, custom Giambattista Valli gown on Ariana Grande. Photo: Steve Granitz/WireImage.
<h2>Billy Porter, 2020</h2><br>Billy Porter's remote-controlled, rhinestone hat was enough to get him on this list. The rest of his teal-and-silver Baja East look was just icing on the cake. <span class="copyright">Photo: Axelle/Bauer-Griffin/FilmMagic.</span>

Billy Porter, 2020


Billy Porter's remote-controlled, rhinestone hat was enough to get him on this list. The rest of his teal-and-silver Baja East look was just icing on the cake. Photo: Axelle/Bauer-Griffin/FilmMagic.
<h2>Lizzo, 2020</h2><br>Glamorous doesn't even begin to describe this Old Hollywood-inspired Versace gown on Lizzo. <span class="copyright">Photo: Steve Granitz/WireImage.</span>

Lizzo, 2020


Glamorous doesn't even begin to describe this Old Hollywood-inspired Versace gown on Lizzo. Photo: Steve Granitz/WireImage.
<h2>Lady Gaga, 2019<br></h2><br>TBT to when Lady Gaga gave Celine's Hedi Slimane her red carpet stamp of approval. <span class="copyright">Photo: Dan MacMedan/Getty Images.</span>

Lady Gaga, 2019


TBT to when Lady Gaga gave Celine's Hedi Slimane her red carpet stamp of approval. Photo: Dan MacMedan/Getty Images.
<h2>Chloe x Halle, 2019</h2><br>Sisters who sing together, coordinate their red carpet fashion together. <span class="copyright">Photo: Lester Cohen/Getty Images.</span>

Chloe x Halle, 2019


Sisters who sing together, coordinate their red carpet fashion together. Photo: Lester Cohen/Getty Images.
<h2>Cardi B, 2019</h2><br>Cardi B came out of her (vintage Mugler) shell for the 2019 Grammys. <span class="copyright">Photo: Dan MacMedan/Getty Images.</span>

Cardi B, 2019


Cardi B came out of her (vintage Mugler) shell for the 2019 Grammys. Photo: Dan MacMedan/Getty Images.
<h2>Taylor Swift, 2016</h2><br>Normally a high-low, two-piece look wouldn't be our choice for a red carpet, but Taylor Swift's Versace look was equal parts glamorous and fresh.<span class="copyright">Photo: Axelle/Bauer-Griffin/FilmMagic.</span>

Taylor Swift, 2016


Normally a high-low, two-piece look wouldn't be our choice for a red carpet, but Taylor Swift's Versace look was equal parts glamorous and fresh.Photo: Axelle/Bauer-Griffin/FilmMagic.
<h2>Rihanna, 2015</h2><br>In our book, Rihanna can do no wrong. But while everything the singer-designer does is a win for us, this bubblegum pink Giambattista Valli gown is a step above the rest. <span class="copyright">Photo: Jon Kopaloff/FilmMagic.</span>

Rihanna, 2015


In our book, Rihanna can do no wrong. But while everything the singer-designer does is a win for us, this bubblegum pink Giambattista Valli gown is a step above the rest. Photo: Jon Kopaloff/FilmMagic.
<h2>Destiny's Child, 2001</h2><br>We didn't even notice the five Grammys on the floor because we were too busy admiring all three of these looks.<span class="copyright">Photo: Steve Granitz Archive 1/WireImage.</span>

Destiny's Child, 2001


We didn't even notice the five Grammys on the floor because we were too busy admiring all three of these looks.Photo: Steve Granitz Archive 1/WireImage.
<h2>Britney Spears, 2000</h2><br>This all-white look on Britney Spears doesn't get the recognition it deserves. <br><span class="copyright">Photo: Kevin Mazur/WireImage.</span>

Britney Spears, 2000


This all-white look on Britney Spears doesn't get the recognition it deserves.
Photo: Kevin Mazur/WireImage.
<h2>Jennifer Lopez, 2000</h2><br>Name a more iconic outfit than J.Lo's Versace Jungle dress. We'll wait. <span class="copyright">Photo: Jeff Vespa/WireImage.</span>

Jennifer Lopez, 2000


Name a more iconic outfit than J.Lo's Versace Jungle dress. We'll wait. Photo: Jeff Vespa/WireImage.
<h2>Mary J. Blige, 2000</h2><br>The diamonds! The shawl! The hot pink color! Mary J. Blige did everything right at the 2000 Grammys.<span class="copyright">Photo: SGranitz/WireImage.</span>

Mary J. Blige, 2000


The diamonds! The shawl! The hot pink color! Mary J. Blige did everything right at the 2000 Grammys.Photo: SGranitz/WireImage.
<h2>Jada Pinkett Smith, 1998</h2><br>It's no wonder Jaden Smith is such a style star today. Just look at this naked dress his mom wore to the Grammys while she was pregnant with him. <span class="copyright">Photo: Ron Galella, Ltd./Ron Galella Collection/Getty Images.</span>

Jada Pinkett Smith, 1998


It's no wonder Jaden Smith is such a style star today. Just look at this naked dress his mom wore to the Grammys while she was pregnant with him. Photo: Ron Galella, Ltd./Ron Galella Collection/Getty Images.
<h2>Lauryn Hill, 1997</h2><br>Laid-back and sophisticated, this red-and-white dress was the winner at the 1997 Grammys red carpet. <span class="copyright">Photo: Kevin Mazur/WireImage.</span>

Lauryn Hill, 1997


Laid-back and sophisticated, this red-and-white dress was the winner at the 1997 Grammys red carpet. Photo: Kevin Mazur/WireImage.
<h2>Aretha Franklin, 1992</h2><br>No one does leopard print and fur quite like Aretha Franklin.<span class="copyright">Photo: Ron Galella, Ltd./Ron Galella Collection/Getty Images.</span>

Aretha Franklin, 1992


No one does leopard print and fur quite like Aretha Franklin.Photo: Ron Galella, Ltd./Ron Galella Collection/Getty Images.
<h2>Prince, 1988</h2><br>Only Prince could pull off <em>literal</em> head-to-toe polka dots. <span class="copyright">Photo: Ron Galella, Ltd./Ron Galella Collection/Getty Images.</span>

Prince, 1988


Only Prince could pull off literal head-to-toe polka dots. Photo: Ron Galella, Ltd./Ron Galella Collection/Getty Images.
<h2>Grace Jones, 1983</h2><br>No one out-styles Grace Jones. No one. <span class="copyright">Photo: Chris Walter/WireImage.</span>

Grace Jones, 1983


No one out-styles Grace Jones. No one. Photo: Chris Walter/WireImage.
<h2>Yoko Ono & John Lennon, 1975</h2><br>From the feathers to the Elvis nametag, Yoko Ono and John Lennon's Grammys looks were undeniably cool. <span class="copyright"> Photo: Ron Galella, Ltd./Ron Galella Collection/Getty Images.</span>

Yoko Ono & John Lennon, 1975


From the feathers to the Elvis nametag, Yoko Ono and John Lennon's Grammys looks were undeniably cool. Photo: Ron Galella, Ltd./Ron Galella Collection/Getty Images.
<h2>Cher, 1974</h2><br>Is it just me, or does Cher's butterfly-covered look from the 1974 Grammys belong on the <a href="https://wwd.com/runway/fall-ready-to-wear-2021/milan/blumarine/review/" rel="nofollow noopener" target="_blank" data-ylk="slk:fall '21 Blumarine runway" class="link rapid-noclick-resp">fall '21 Blumarine runway</a>? <span class="copyright">Photo: Michael Ochs Archives/Getty Images.</span>

Cher, 1974


Is it just me, or does Cher's butterfly-covered look from the 1974 Grammys belong on the fall '21 Blumarine runway? Photo: Michael Ochs Archives/Getty Images.

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