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Miley Cyrus Redefines Menswear Chic on NYC Streets

by Demos

Miley Cyrus is once again proving that she can wear menswear better than most men. Ahead of her upcoming album Something Beautiful, the pop star has been spotted in New York City showcasing two fresh takes on a classic finance-bro staple: the striped button-down shirt.

Earlier this week, after a stylish studio session, Cyrus stepped out in an oversized gray and white Oxford shirt that blended comfort and confidence. By leaving a few buttons undone, she created a laid-back vibe that gave just a peek at the black lace bra beneath—a clever feminine contrast. She finished off the look with wide-leg trousers, pointed-toe heels, and square-framed glasses, adding an air of effortless sophistication.

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The following morning, on her way to a photo shoot, Cyrus doubled down on her fashion-forward twist to office wear. She wore a sheer black-and-white striped button-down layered over a scoop-neck tank. Like the day before, the peek-a-boo elements—this time sheer fabric instead of an unbuttoned neckline—added visual interest to the otherwise traditional silhouette. She paired the look with slightly baggy blue jeans, heeled black boots, and the same chic eyewear from the day before.

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Though Cyrus has no shortage of dramatic stagewear—she recently teased Something Beautiful in a series of vintage Thierry Mugler looks—her recent daytime style choices show that she can turn even the most classic garments into fashion statements. In just 48 hours, she’s made a compelling case for the versatility of men’s shirting, using it as a foundation for polished, personality-filled streetwear.

Between album prep and public appearances, Cyrus clearly has a packed New York schedule. But if her recent looks are any indication, she might want to take a quick detour downtown—to show the Financial District how button-downs are really done.

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