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- Standout looks of the 2020s: modern glamour and bold reinvention
- 2010s flashpoints: drama, art and high-concept fashion
- Turn-of-the-millennium moments that still resonate
- 90s and earlier: classic glamour and transformational red carpet style
- Men’s fashion and gender-bending moments on the Grammy carpet
- Accessories, jewelry and finishing touches that elevated looks
- Fashion that shaped headlines and culture
The Grammys have long been the red carpet where music stars take the biggest fashion risks. From glittering couture to unexpected menswear, the show delivers looks that dominate headlines and social feeds. Below is a fresh look at the most memorable Grammy outfits — the daring, the glamorous and the downright iconic.
Standout looks of the 2020s: modern glamour and bold reinvention
- Bad Bunny, 2026 — Schiaparelli’s first couture menswear made headlines: a black velvet tuxedo corseted at the waist and lace-up details at the back.
- Taylor Swift, 2025 — A scarlet Vivienne Westwood gown topped with over 60 carats of Lorraine Schwartz rubies, including a custom thigh chain she helped design.
- Sabrina Carpenter, 2025 — A feather-trimmed JW Anderson halter offered fairy-tale vibes, anchored by a bold 50-carat Chopard necklace.
- Miley Cyrus, 2024 — A punk-infused Maison Margiela mini made from thousands of safety pins fused craftsmanship with rock energy.
- Olivia Rodrigo, 2024 — A vintage Versace gown from 1995, revived with red beadwork to echo her song “Vampire.”
- Harry Styles, 2023 — A colorful crystal-mesh jumpsuit by Egonlab and Swarovski that shimmered with every step.
- Doja Cat, 2022 — A mint Atelier Versace gown paired with a sculptural blown-glass Coperni clutch for a futuristic-meets-feminine look.
- Dua Lipa, 2021 — A bedazzled pink butterfly gown from Atelier Versace that felt theatrical and chic.
- Megan Thee Stallion, 2021 — A bold orange Dolce & Gabbana dress with a voluminous bow, turning heads on arrival.
- Ariana Grande, 2020 — A voluminous gray Giambattista Valli haute couture creation that played up her signature glamour.
- Lil Nas X, 2020 — A hot-pink Versace ensemble that matched the Western energy of his breakthrough hit.
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2010s flashpoints: drama, art and high-concept fashion
- Cardi B, 2019 — Emerging from a shell in archival Mugler couture, she channeled Botticelli with layers of pearls.
- Lana Del Rey, 2018 — A celestial Gucci gown and coordinating crown created an ethereal red carpet moment.
- Rihanna, 2017 — An Armani Privé crop top and sweeping skirt showcased tattoos and high jewelry in a bold mix.
- Selena Gomez, 2016 — A shimmering Calvin Klein cutout look that married simplicity with sex appeal.
- Ciara, 2016 — An Alexandre Vauthier couture gown that highlighted legs and confidence.
- Madonna, 2014 — A menswear-inspired Ralph Lauren suit that proved classic tailoring can be radical on the carpet.
- Katy Perry, 2014 — A musical-themed Valentino haute couture gown that balanced whimsy with polish.
- Nicki Minaj, 2012 — A red satin Versace robe that sparked conversation, complete with an unexpected papal-inspired partner.
- Lady Gaga, 2010 — An interstellar Armani Privé number that remains one of her most memorable fashion statements.
Turn-of-the-millennium moments that still resonate
- Gwen Stefani, 2006 — An ombré animal-print gown from her L.A.M.B. line, worn while expecting and still stylishly bold.
- Destiny’s Child, 2001 — Coordinated green-and-gold ensembles designed by Tina Knowles that matched a winning night.
- Jennifer Lopez, 2000 — The plunging jungle-print Versace dress that caused global search frenzy and rewrote red carpet history. This look defined an era.
- Britney Spears, 2000 — An all-white Old Hollywood silhouette with fur and glamour that felt timeless.
- Shania Twain, 1999 — A shimmering white Marc Bouwer turtleneck gown that merged country star polish with high fashion.
90s and earlier: classic glamour and transformational red carpet style
- Jada Pinkett Smith, 1998 — A sheer, sparkly dress that proudly showed her baby bump and redefined pregnancy dressing.
- Mary J. Blige, 1996 — Head-to-toe leopard print that embraced bold pattern play.
- Selena, 1994 — A white embellished halter gown that remains an enduring image of Tejano elegance.
- Mariah Carey, 1991 — An embellished little black dress worn as she collected her first Grammys.
- Whitney Houston, 1986 — A goddess-blue Travilla Couture gown the singer wore when she won her first Grammy.
- Michael Jackson, 1984 — The embellished military jacket and sparkling glove he wore while sweeping awards with Thriller.
- Cher, 1974 — A butterfly-bedecked Bob Mackie creation that endures as a costume classic.
Men’s fashion and gender-bending moments on the Grammy carpet
- Bad Bunny, 2026 — A corseted tuxedo that blurred masculine and couture codes.
- Harry Styles, 2023 — A crystal mesh jumpsuit that embraced color and shimmer in menswear.
- Lil Nas X, 2020 — Vibrant Versace looks and a fearless approach to red carpet identity.
- Michael Jackson, 1984 — Iconic embellished tailoring that became part of pop visual history.
Accessories, jewelry and finishing touches that elevated looks
- Taylor Swift’s ruby thigh chain paired high jewelry with a high-fashion gown.
- Sabrina Carpenter’s 50-carat Chopard necklace turned her dress into a jeweled statement.
- Rihanna’s Chopard diamonds and bold ink combined couture with personal identity.
- Doja Cat’s Coperni blown-glass purse proved that unconventional accessories can steal the scene.
Fashion that shaped headlines and culture
- Jennifer Lopez’s 2000 Versace — A viral moment that changed how red carpet images circulate online.
- Britney and Destiny’s Child — Turn-of-the-century glamour that influenced early-2000s style.
- Lady Gaga and Madonna — Artists who used the Grammys to push costume-level fashion into mainstream conversation.
