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.
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1. Leather skirt with an oversized sweater
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
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
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
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.
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5. Classic leather skirt with a button-down shirt
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.
