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Transitional dressing isn’t always easy, but Halle Bailey recently pulled it off with a cozy yet stylish date-night outfit. In her latest Instagram post, the singer and actor shared a series of selfies, likely moments before a night out with her boyfriend, rapper DDG. Styling a plunging cropped knit top with formfitting black pants resembling leggings, Bailey accessorized with tan sandals, a black leather chain purse, and gold earrings. Her deconstructed sweater was a unique, striking choice, featuring a large front cutout, mock neck, and detached sleeves.

Romantically linked since January 2022, Bailey and DDG made their red carpet debut at the 2022 BET Awards in June; they matched in sleek black outfits: Bailey in a black Mônot set with a plunging neckline and hip cutouts, and the rapper in a Prada turtleneck and vest, finished with stacked chain necklaces. For a more casual evening with DDG in London, “The Little Mermaid” star chose a velvety-green two-piece set with a crop top and slitted maxi skirt.

Aside from her date-night style, Bailey has brought out some equally chic looks all summer. Inspired by her “The Little Mermaid” character, she stunned in a green multimedia coordinating bra-and-skirt set by Joanna Prazmo for Variety’s 2022 Power of Young Hollywood issue in August. And at the magazine’s corresponding Power of Young Hollywood even, she donned a white ’90s slip dress from August Getty Atelier. Just a week prior, she appeared in Latto’s “It’s Givin” music video wearing a pinstripe bikini suit with tiny tailored bottoms.

Take a closer look at her latest outfit ahead.

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