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Chloe Bailey Talks ‘Praise This’ & Overcoming Imposter Syndrome in Ruched Dress & Stiletto Boots on ‘Drew Barrymore’

The Grammy-nominated singer opened up about overcoming imposter syndrome and touring with Beyoncé on 'The Drew Barrymore Show.'
Chloe Bailey, The Drew Barrymore Show, Dress, Celebrity Style
Chloe Bailey at the "Mufasa: The Lion King" premiere at Dolby Theatre on December 09, 2024 in Los Angeles, California.
Chloe Bailey at The Fashion Awards 2024 held at the Royal Albert Hall on December 02, 2024 in London, United Kingdom.
Chloe Bailey at the 2023 MTV Video Music Awards held at Prudential Center on September 12, 2023 in Newark, New Jersey.
NEW YORK, NEW YORK - OCTOBER 27: Chloe Bailey attends Bette Midler's Annual Hulaween Bash at Cipriani South Street on October 27, 2023 in New York City. (Photo by Arturo Holmes/Getty Images)
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Chloe Bailey looked pretty in purple while appearing on “The Drew Barrymore Show.”

On Thursday’s episode of the morning talk show, the Grammy-nominated singer sits down with Barrymore for an intimate chat about seeing her younger sister Halle Bailey in “The Little Mermaid” trailer for the first time during the Oscars, touring with Beyoncé, her new movie “Praise This” and how she overcame imposter syndrome.

Chloe looked stunning for the appearance. The “How Does It Feel” musician wore a purple ruched off-the-shoulder dress. The piece had a plunging square neckline, a daring slit at the back and a form-fitting skirt.

Chloe Bailey, The Drew Barrymore Show, Dress, Knee-High Boots
Chloe Bailey appears on “The Drew Barrymore Show” on April 13, 2023.

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Taking things up a notch, the R&B songstress accessorized with oversized hoop earrings, layered choker necklaces and a collection of diamond rings. Chloe styled her hair in a high ponytail and let two curly strands frame her face. As for makeup, the “Have Mercy” hitmaker went with peach eyeshadow and a glossy neutral pout.

Giving her look a sleek finish, Chloe slipped into a pair of purple knee-high boots. The leather silhouette had a sharp, triangular pointed toe and was set on a thin stiletto heel.

Popularized in the ‘60 go-go era, knee-high boots leave the wearer’s knee exposed, but cover the calves. Often worn with skirts, the style is a wise choice in fall and winter for protecting the leg from the elements while still allowing the wearer to show some leg.

Chloe Bailey, The Drew Barrymore Show, Dress, Knee-High Boots
Chloe Bailey appears on “The Drew Barrymore Show” on April 13, 2023.

Chloe remains trendy when it comes to her footwear choices. The “Swarm” actress has been spotted in several styles like thong sandals and chunky sneakers from brands like Tamara Mellon, Balenciaga and many more. She also wears Allbirds sneakers when off-duty. Additionally, the multi-hyphenate phenom has an extensive resume in the fashion industry, having appeared in campaigns and runways for Fendi, Dolce & Gabbana and Louis Vuitton.

Bailey’s highly anticipated solo debut album “In Pieces” is available to stream on all music platforms. The album includes new singles and features from the likes of Chris Brown, Missy Elliot and Future.

PHOTOS: Discover Chloe Bailey’s fashion evolution through the years in the gallery.

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