The Only Guide You Need to Style Your Leather Jacket in 2025

I’d like to propose an addition to the physiological level of Maslow’s hierarchy of needs. In addition to food, water, and shelter, every man, woman, and child also needs a leather jacket.

If you clicked on this article, you probably own a leather jacket already, so congratulations on doing life right. The next obvious step, after securing one or two leather jackets (or three, or four), is mastering the art of wearing one.

While I believe leather jackets are a versatile, timeless, and classic staple that every wardrobe deserves to have, I also believe that leather jackets are unfortunately and notoriously difficult to pull off. Wear one the wrong way, and you risk looking like you’re dressed up as a Greaser for a low-budget middle school production of The Outsiders. But if you wear one the right way, in a way that looks natural and effortless, you’re bound to look cool and collected. My job is to make sure you’re always going the latter route.

A leather jacket is an every-occasion garment, so below, I’m going to walk you through some foolproof ways of dressing it down, dressing it up, and going full-on main character in it.

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Luckily, a leather jacket tends to look fan-fucking-tastic with a simple T-shirt and jeans. Usually, a looser fit is a little better, ’cause if you go too tight, you tread that Greaser line a bit. But regardless, a plain tee, a ringer tee, a graphic tee (especially a vintage band tee—classic), they’re all safe bets.

I’ve always been partial to the hoodie-underneath-jacket look, too. It has a distinctly “A-lister celebrity at the airport” vibe to it. You’ll definitely need a bigger leather jacket to achieve that look, and when you do, feel free to throw on a baseball cap and some shades, too. And if you don’t want to go for a hoodie, opt for a henley instead—it’s still laid-back, casual, and easy, and the leather jacket toughens it up a little bit.

As for the pants—jeans are never a bad bet. And depending on the fit and style of your leather jacket, you can also try chinos (brown leather will look best, and probably a bomber or racer style, too; leave the moto jackets to your denim). Sneakers and loafers are obvious safe bets, but if you really want to get playful with it, pull on a pair of boots: cowboy boots are a personal favorite, but a chukka or Chelsea never hurt anyone, either.

You should never think of your leather jacket as a piece that can’t be dressed up, ’cause it very easily can be. An outfit combo I always love: leather jacket, button-down shirt, tie. We’ll get to the pants in a second, but this top part works with any and every style of leather jacket, from a motorcycle jacket to a trucker jacket.

Pleated pants are a solid move, especially with a leather belt that matches the leather of your jacket. Even if you go sans tie, a leather jacket with a button-front shirt (and feel free to have fun with it, BTW—you don’t have to stick with white, reach for a playful print or pattern!) is never a bad moment to pull out your favorite dress pants.

You can also keep on the elevated plane by wearing a nice sweater with your leather jacket. The contrast between soft and cozy versus edgy and cool is nice on the eyes, and it’s hard to go wrong with your favorite woolly number on.

Leather shoes are the way to finish the look off: an Oxford, a derby, a loafer, or even a sleek ankle boot.

At the end of the day, a leather jacket has distinct vibes. A leather jacket is rock ‘n’ roll. A leather jacket is badass. And sometimes, styling one just means leaning into it, and letting the leather jacket guide you.

If the vibes aren’t calling to you, let me try to get you into the proper headspace. Ask yourself how a rock star would wear a leather jacket—what would Lenny Kravitz do?—and go from there. Pair it with tight pants (skinny jeans are cool, ripped jeans are great, leather pants are iconic) and a heeled, pointy boot. Sunglasses, obviously. Some jewelry—throw on a ring and a necklace, maybe even a statement belt and a scarf, if you have one. Trust me, all of the above will look more natural with a leather jacket than without one.