If you want to know what to wear with a leather skirt this fall, you could just look to Taylor Swift. The singer stepped out recently in New York City for a screening of Toy Story 5 in a quintessential office outfit: black leather pencil skirt, crewneck knit sweater, and slingback heels. (See the full look here.)
If that’s a little too corporate for you, we’ve seen plenty of other leather skirt outfits from Swift. Her favorite way to style a miniskirt, for example? With black booties and a slinky little top.
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As Swift demonstrates, a leather skirt is a fall and winter staple worth having in everyone’s closet. It’s just so versatile! A white button-down shirt and leather skirt combo is the first thing that comes to mind—it’s a classic look for a reason, after all—but it’s also a piece that you help you lean into 2026 fashion trends that’ll take your outfit even further. For example, lately I’ve been loving prep-inspired looks like rugby polos, which are having a major moment right now, or mixing in animal prints (also super trendy).
Here’s what to wear with a leather skirt to look stylish this season—and beyond—inspired by our favorite celebrities and street style stars.
