Toni Braxton's Inappropriate Outfit At The 2001 Grammys Will Always Haunt Her

Though she has been a fixture in R&B music, acting, and reality shows for decades, Toni Braxton was arguably at the height of her popularity at the beginning of this century. In 2000, her album "The Heat" debuted, with the song "He Wasn't Man Enough" receiving all kinds of accolades, including two Grammy nominations in 2001. She ended up taking home the trophy for best female R&B vocal performance. But her big win wasn't what had people buzzing that year — it was the inappropriate outfit that showed more than just a lot of skin.

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The scintillating Richard Tyler dress featured a deep dip at the front and slits that went way past the boundary of thigh-high on the sides. The daring 'fit is still one of the most-discussed looks of all time and frequently deemed one of the most inappropriate outfits in Grammys history. As she told People at the time (via The Hollywood Reporter), "I've always gone a little risqué with all my other [awards show outfits]. I decided that before I got married and had babies, I'd wear this."

At the time of the 2001 Grammys dress, Toni Braxton was actually already married to singer Keri Lewis, whom she wed in 1998 and divorced in 2013. She did go on to have those babies not long after: The couple's two sons, Denim and Diezel, were born in 2001 and 2003, respectively. But she didn't retire her love of revealing outfits. She's still confidently showing off her bod in her 50s, alerting the world that sexiness doesn't have an age limit.

The "Un-Break My Heart" singer is among the famous older women who don't seem to age. In May 2020, at age 52, the star posted a bikini selfie to her Instagram page. Fans added a lot of flame emojis, with one writing, "Still got it." In November 2025, at age 58, the "Dancing with the Stars" alum again showed off her fine form in a chartreuse Gucci dress for Kris Jenner's 70th birthday party. One follower wrote, "Just like the taste of greatest wines, a real lady only gets better when time flies by."

Feeling inspired, but don't need a red-carpet naked dress? Then check out these 5 youthful outfit ideas that are beautiful on older women.