Chloe Bailey is *that* girl. The singer-songwriter made her rise to fame in the musical duo Chloe x Halle with sister Halle Bailey, and has since launched her own solo music career! Keep reading to see photos of her best red carpet moments over the years.

Chloe and Halle first entered into the spotlight in the early 2000s after posting singing videos covering songs on YouTube. They were eventually discovered by Beyoncé and released three albums under the name Chloe x Halle.

Throughout their career, the siblings have been known as a unit — even sharing joint social media accounts — until January 2021 when they shocked fans by making separate Instagram and Twitter pages.

“What I really appreciate with Halle and I is even when we are together constantly we never try to have each other compromised,” Chloe explained during a March 2021 interview with The Breakfast Club‘s Angela Yee. “We are both so alike and so similar, but we’re also so different. And how we are as individuals shine through with our group and people are getting to know us more individually as well.”

The pair have since gone on to work on their respective solo careers, with Halle focusing on acting as Ariel in Disney’s live-action The Little Mermaid in April 2023, and Chloe dropping her first solo album, In Pieces, in the same year.

Chloe told Rolling Stone about how difficult it was to put out her first album by herself during an interview in March 2023.

“The biggest risk is the whole album itself,” she began. “There were so many people in my life — I’m not talking about online internet trolls, but people I was close to — who told me I couldn’t do this. Who said I wouldn’t be good enough to do this on my own. That was scary as shit actually doing it, because there were times where I believed them. I believed the negative things being told to me. I just had to keep trusting myself, and it’s still hard even now to try to not doubt myself and talk myself out of the blessings that I’m receiving.”

Click through our gallery to see Chloe’s red carpet transformation over the years.

Love J-14? Be sure to subscribe to our YouTube channel for fun, exclusive videos with your favorite stars.