How to Wear a Leather Jacket: From Rock and Roll Grit to A-Lister Shine

The easiest way to an instantly look cool.

Leather jackets are pretty much the coolest item you can buy. Nothing quite says A-lister chic than a quality leather jacket and you’re sure to stand out when you wear one.

The most interesting thing about a leather jacket is how they go with both high-end and scuzzy looks in a way that not many other pieces do. What I mean by this is that when wearing a leather jacket you have two highly contrasting options for how to take your look:

  1. You can lean into the jacket’s air of rock and rock sleaze and dress it down with pieces like worn jeans and boots.
  2. You can lean into the jacket as a high end piece of premium clothing and dress it up with well-fitted slacks, shirts, and quality sweaters.

The look you go for will depend on your jacket. A biker jacket with lots of studs and zips will naturally go with the former style. While a pristine collared jacket will naturally go with the latter.

How to Wear a Leather Jacket: 7 Styles

With Worn Jeans and Boots

Distressed Jeans Leather Jacket

This is perhaps the quintessential way to wear a leather jacket. Pairing it with worn (even ripped) skinny jeans and boots gives you a timeless rock star look. I think this look would also go well with canvas shoes.

With Smart Pants and a T-Shirt

Leather jacket black pants canvas shoes

Everyone knows that leather jackets go with jeans. But they also go well with smart slacks. I like wearing mine with dark pairs in black, charcoal, or gray. Finish the look off with a pair of canvas sneakers to dress the jacket down or a pair of leather shoes to dress it up.

With all Black Pieces

Black leather jacket jeans

Wearing your leather jacket with other all-black pieces gives you a look that still has plenty of rock star vibes but gives a moodier look overall. I like the idea of wearing them with black slim jeans and a pair of black boots like in the image above.

With a White T-Shirt

Leather jacket white t-shirt

Wearing a leather jacket with a white t-shirt is another classic leather jacket outfit. It can be cliched, but ultimately the contrast between the black of the jacket and the white of the t-shirt always looks good. Pairing the pieces with smart slacks is a stylish alternative to jeans. I like how the image above finishes the look off with a long chain necklace.

With Dark Jeans and a Shirt

Work Boots Skinny Jeans

Dark blue jeans, a shirt, and a leather jacket is a great outfit to wear next time you plan to hit the bars at the weekend. I like how the outfit above finishes the look off with a pair of leather boots. Minimalist sneakers would work just as well.

With a Hoodie and Boots

Leather jacket hoody

Throwing a leather jacket over a hoodie is a simple look to pull off. I like the idea of wearing the jacket with a plain, dark hoodie rather than a colorful one or one with a logo. Finish the look off with jeans and sneakers. It’s also the perfect way to stay warm when a leather jacket doesn’t quite cut it on its own.

With a Black Turtleneck

Leather jacket black turtleneck

Wearing a turtleneck with a leather jacket is a good way to combine two pieces that grab the eye. A black turtleneck and black jeans goes well with the jacket, but you could also mix up the colors. For example, by wearing an off-white turtleneck with a black jacket. Finish the look off with boots or leather shoes (yes, you can wear leather shoes with jeans). If you don’t have a turtleneck, try wearing with a regular sweater. And you could also swap out jeans for slacks.

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Duncan Elder

Duncan is the founder and editor-in-chief of The Boardwalk. He's a menswear writer who has spent the last 15 years developing his own sense of style, which lies at the cross-section of mid-noughties indie and Uniqlo-inspired minimalism.

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