A leather skirt is a fall and winter staple in my closet. So if you’re wondering what to wear with a leather skirt 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 shirts, 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 cosy jumper is another autumn 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 are 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.

2. Leather skirt with rugby polos

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It’s official: Rugby shirts are everywhere this fall. I personally love the sporty and preppy vibe that they add to my outfits. A striped one in particular is a great statement piece with a leather maxiskirt (for work) or a brown leather mini (for a night out). In terms of footwear, you can pair it with loafers, square-toe boots, or pumps.

3. Monochramatic leather on leather

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Yes, it’s true, you can never go wrong with an all-black outfit. While I love an edgy black leather-on-leather moment, the colour trends this season are all about grapes, purples, and wines. A burgundy shade can go well with a matching cropped leather jacket or a leather trench coat in the same shade.

READ MORE: How to style a leather jacket like a fashion editor.

4. Leather skirt with prints

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Animal prints have been dominating runways since the spring of this year. And based on Fashion Month’s latest SS26 runway shows, it seems the trend is here to stay for a while. Zebra stripes in particular might seem tricky to style, but they’re a fun way to add pattern to your neutrals. (Bye, winter greys!) If you buy one thing this fall, let it be a comfy fur coat to go with all your skirts and bottoms.

5. Classic leather skirt with a button-down shirt

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Of course, I had to include outfit ideas for how to style a black leather skirt and a white button-up – or printed shirt, for that matter. While it sounds simple, the secret to styling this classic is all about a long winter coat and curated accessories. Big shoulder bags (in my case, a trusty work tote), cool shades, ties, and socks are perfect for a sophisticated corporate cutie feel.

Or, take a cue from German influencer Leonie Hanne, who was recently spotted attending the Calvin Klein fashion show wearing a leather skirt outfit with a lace triangle bra underneath and black tights.

After more styling hacks? Discover how to style an oversized shirt, how to style loafers and how to style a trench coat.