It’s no secret Jennifer Lopez is one of the most fashionable women in Hollywood. In fact, the longtime entertainer has stepped out in more than her fair share of iconic looks over the years — including some braless moments we still talk about today.

By this point, we suspect the image of Jennifer’s 2000 Grammy Awards Versace gown is dancing around in your head. After all, it’s regarded as one of the most daring style choices in the last two decades.

“Usually, if you come to a fitting of mine, there’s like are tons of dresses, tons of shoes, it’s crazy. There’s always so many choices, but this day, we really had a choice between two dresses. One was kind of a white dress or something like that and the other was the Versace jungle print dress,” Jennifer recalled in an April 2019 YouTube video.

According to J. Lo, her stylist tried to persuade her to wear the white gown because several other A-listers, including Donatella Versace herself, had already been photographed in the dress. Even so, the NYC native decided to try it on anyway. “‘That’s it! Don’t even talk about it. That’s the dress!’” she recalled her then-manager, Benny Medina, exclaiming.

“We hit the red carpet, and it was a frenzy! The flashes started going in a way that it’s not usually,” Jennifer continued. “There was an extra kinetic energy there.” Although the mother of two, who shares twins Max and Emme with ex-husband Marc Anthony, didn’t take home a Grammy Award that night, she did solidify herself as a red carpet legend.

“One dress can change the trajectory of how people dress for the next 10 years. It’s a crazy impact that fashion can have and those fashion statements can have in solidifying a personality, a moment, a style, a movement, all of those things,” Jennifer said. “It was a really exciting time.”

Since then, J. Lo, who is currently dating Ben Affleck, has continued to wow fans everywhere with her outfits.

Scroll through the gallery below to see Jennifer Lopez’s best braless moments over the years. 


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Tyler Cowan