From Jennifer Lopez’s iconic sheer Versace dress in 2000 to Britney Spears’ angelic Y2K look that same year, here are all the most audacious ensembles to have ever graced the Grammys red carpet.

Here's a look at the boldest looks she's ever worn, from see-through dresses to silver armor ... It made for one of the most daring looks Zendaya wore throughout the "Dune" press tour.

Olivia Rodrigo walked the red carpet of the 67th Grammy Awards in an exposing Versace dress that was a stark departure from ...

Grammy nominee Jacob Collier stepped onto the red carpet in a bold, multi-colored suit paired with matching pants, a navy ...

Madison Beer attended the 2025 Grammys wearing an ornate sheer Miss Sohee dress with a corset-style bodice and embroidered train. Chrissy Teigen also opted for a daring dress, wearing a sheer ...

Blake Lively attended the 2009 Met Gala in a Versace dress with a sheer sleeve, a thigh-high slit, and a plunging neckline. Lively's Marchesa minidress at the 2011 CinemaCon Awards had a sheer ...

Ernesto Ruscio/Getty Images Entertainment/Getty Images She also sported many a plunging dress to promote the launch of her most recent fragrance, Nightcap, including this pale pink number that ...

Backless tops, see-through dresses, and neon outfits have all ... The outfit was memorable and one of the most daring ever seen at the event. Love completed it with silver sparkles dusted across ...

Backless tops, see-through dresses, and neon outfits have all had their moment ... The outfit was memorable and one of the most daring ever seen at the event. Love completed it with silver sparkles ...