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While the Oscars, Golden Globes, and Emmys are known for their high glamour, the Grammys take the cake for adventurous red carpet fashion. It’s the only place to witness Taylor Swift in a striking ruby thigh chain, Jennifer Lopez making headlines in a deep-cut Versace with a tropical print, or Rihanna flaunting her tattoos in a chic couture crop top. Below is a retrospective of some of the most memorable outfits at the biggest night in music.

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Bad Bunny, 2026

The Puerto Rican sensation snagged the Album of the Year award for “Debí Tirar Más Fotos” while donning Schiaparelli’s debut couture menswear piece: a luxuriously corseted black velvet tuxedo that highlighted his silhouette and featured an intricate lace-up back.

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Taylor Swift, 2025

A vision in red, Swift dazzled in a Vivienne Westwood gown and over 60 carats of Lorraine Schwartz rubies, including a bespoke thigh chain. Whether the ‘T’ stands for Taylor or Travis, Swift surely carried the night.

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Sabrina Carpenter, 2025

The pop starlet made a striking impression in a Cinderella-inspired JW Anderson gown adorned with feathers and a breathtaking 50-carat diamond necklace from Chopard.

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Miley Cyrus, 2024

Rocking the classic rock ‘n’ roll style, Cyrus wowed in a metallic Maison Margiela mini crafted from 14,000 safety pins, complemented by her signature voluminous hairstyle.

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