Chloe Bailey’s 13 Sexiest Moments Ever
BY Malcolm Trapp / 4.24.2025
When Chloe Bailey went solo in 2021, everyone suddenly had opinions about what she wore, how she moved, and exactly how a 20-something woman should or shouldn’t present herself online. However, her debut single, “Have Mercy,” arrived as a chart-topping middle finger to anyone accusing her of doing too much, which, in the Grammy-nominated singer’s case, more often than not meant celebrating her own reflection.
The record serves as a clear departure from Chloe x Halle, her sister duo with Halle Bailey. If nothing else, the artist is refusing to dial it back for anyone’s comfort but her own, and honestly, good for her. Chlöe keeps delivering a necessary reminder that sexiness doesn’t belong to the audience but to its rightful owner. She’s only doubled down on even more unapologetic moments on 2023’s In Pieces, award shows and a number of Instagram posts. Below, Rap-Up took a look at the “Treat Me” singer's 13 sexiest moments of all time.
1. The “Have Mercy” Music Video
The Atlanta native's solo debut single, “Have Mercy” — also her well-deserved first Billboard Hot 100 hit — was her way of flipping off everyone who has ever criticized her for showing too much skin in the months leading up to its release. Wearing gym gear, sparkling bikinis and other equally jaw-dropping looks in the track’s accompanying visual, she portrayed a modern Medusa who seduces men into a sorority house before turning them into stone. “Lord, have mercy” indeed.
2. St. Lucia Carnival 2024
It makes sense that Chlöe would break the internet again at her “favorite time of year,” and frankly, it might be ours now, too. The songstress wore multi-colored feathers, a heart-shaped headdress and jeweled accents, courtesy of designer Natalie Fonrose, for her second time attending the St. Lucia Carnival.
3. 66th Grammy Awards
Though she somehow wasn’t nominated that year— In Pieces definitely deserved better — Chlöe walked the red carpet at the 66th Grammy Awards in a black-and-gold, one-shoulder gown by designer Gaurav Gupta. The look gave us a bit of everything: midriff, décolletage and the debut of her new autumn-inspired hair color.
4. Breaking The Internet With Her Mirror Selfies
Sharing a series of pictures of herself on Instagram, Chlöe wore a black lace corset with a matching pair of undies. "Send him new pics in that outfit you like," she captioned the mirror selfies. Ice Spice and Anitta practically summed up exactly what everyone else was thinking in the comments: “Hot.”
5. The “How Does It Feel” Music Video With Chris Brown
Obviously not without a little controversy, the Chris Brown-assisted track “How Does It Feel” proved to be one of the many highlights from the singer’s debut album. The Arrad Rahgoshay–directed video delivered plenty of steamy moments between the duo, who played ex-lovers, plus a much-needed reminder that Chlöe’s choreography remains undefeated.
6. 35th Annual GLAAD Media Awards
The Parkwood Entertainment signee was serving red-carpet energy — and a little butt cleavage — at the 2024 GLAAD Media Awards, where she snagged an Image Award and gave fans the first live performance of "FYS." Her floor-length dress notably featured a back slit held together by corset-style stitching. “Let’s give it up for the back of the dress,” she captioned her Instagram post. “Only right to have a little booty out for the babes.”
7. The Silhouette Challenge
Normally, TikTok’s viral Silhouette Challenge was set against red lighting to the tune of Doja Cat’s "Streets." However, Chlöe took things in another direction. She danced to Jeremih’s "All The Time" while wrapped up in purple hues reminiscent of Beyoncé’s iconic “Partition” music video.
8. Her ‘Trouble In Paradise’ Cover
Trouble In Paradise, Chlöe’s second solo effort, received glowing reviews, and rightfully so. The cover featured the singer in a neon green dress submerged in water, while the 16-song effort itself served up gems like "Same Lingerie," "Temporarily Single" and “Want Me,” her much-anticipated reunion with Halle.
9. Wearing Pink Lingerie For Valentine’s Day
Though she was her own Valentine — seriously, shame on every man who’s dropped the ball with her — Chlöe seemed to make a pretty compelling case that Valentine's Day is criminally underrated as far as holidays go. She wore pink lingerie adorned with red hearts and completed the look with white heels and hoop earrings.
10. The “Surprise” Music Video
Another early highlight from Chlöe’s solo era, "Surprise" saw the singer strutting around in Balenciaga underwear and cozying up with model and actor Broderick Hunter. "Surprise, slip my panties to the side," she sings, following up with lines like, “Build me up, baby, give me that wood / Make it gangsta, 'cause I like it real hood.” It’s arguably one of her least subtle songs.
11. Nearly Naked For YITTY
“I love this bodysuit [because] it hugs all the right places,” Chlöe said about YITTY, and she wasn’t exaggerating. In 2024, the musician was announced as the face of the shapewear label’s Nearly Naked collections, posing in their thong bodysuit, sculpting dress and plenty of other curve-enhancing pieces. “What I love most about my body would definitely have to be my curves,” she explained to the brand. “I’ve had my curves ever since I was a little girl, and through growth, I’ve learned to appreciate and love them.”
12. Her HelloBeautiful Cover
The Praise This star is the queen of covers, whether she's flipping someone else's hit or gracing the front page of magazines. For HelloBeautiful’s August 2024 cover, she stunned in a fishnet dress from Tom Ford. It’s just one more reminder that she's easily among R&B's most gorgeous women.
“The fact of the matter is that, [as] women, we are multifaceted. We have so many layers. Yes, I’m so quirky and weird and corny, but then there’s moments where I feel absolutely sexy and confident,” she told the publication.
13. Getting “WET” In Mowalola
Even though Ye spent most of 2024 knee-deep in controversy again, his “WET" tank tops somehow still managed to sweep the internet and what feels like every Instagram baddie’s feed. Here, Chlöe wore the romper version of Mowalola’s viral design, proving once more that she looks good in something as basic as a one-piece.