A leather skirt is a fall and winter staple in my closet. So if you’re wondering what to wear with one this season, I can think of at least five different ways to style them. (All of which I’m sharing below.)
While a white button-down shirt and leather skirt combo might be the first thing that comes to mind—it’s a classic look for a reason, after all—I encourage you to lean into 2025 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 to elevate my outfits.
Here’s what to wear with a leather skirt to look stylish this season—and beyond.
1. Leather skirt with an oversized sweater
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When the temperature starts to drop, one easy way to dress is by leaning into comfort. A cozy sweater is another fall wardrobe essential, and an oversized one goes well with a leather midi or mini silhouette for a nice contrast in fabrics. Plus, a roomier top and a slim-fitting skirt is a great way to add structure to your outfit; similar to styling pencil skirts, it works best with heels and slingbacks. If you want to give this leather skirt outfit an even more glossy look, add knee-high boots.
Quince Mongolian Cashmere Fisherman Turtleneck Sweater
Hudson Reconstructed Skirt
Vince Boiled Cashmere Funnel Neck Pullover
A.L.C. Marta Straight Leather Midi-Skirt
2. Leather skirt with rugby polos
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