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Style December 18th, 2023

6 Leather Jacket Outfit Ideas For Winter

Style December 18th, 2023

That Don’t Look Like Every Other Leather Jacket Outfit

As someone who’s been into menswear and men’s style very publicly for over a decade now, you might think that I’ve got the whole “how to dress” and “what to wear with fill in the blank” thing down. In some cases, I’d say that’s true — give me a suit or sport coat and I can put some decent outfits together pretty quickly. But in other areas, particularly more casual styles of dressing, it often doesn’t come that easy. And I feel like I typically struggle the most when it comes to leather jacket outfits.

Why is that?

So, you know that one of the things I value most when it comes to building my wardrobe is versatility. And I feel like leather jackets often come across as something of a one-trick pony. Like, if you Google “mens leather jacket outfits” what you see in the image results is — in general — basically all the same thing. You see a somewhat douchey looking guy in a leather biker jacket wearing a t-shirt, too tight jeans, and some type of boot. And maybe he’s got a beard — but not like mine.


Cool . . . ahem.

I guess what I’m saying is that as someone who admittedly struggles in the “what to wear with a leather jacket” department, there’s not a whole lot of inspiration out there to draw from and I’m at the age where that whole rock and roll look thing isn’t really going to work for me.

Maybe you understand exactly where I’m coming from. Or maybe not! But I decided to put this post together for three reasons. First, as a styling exercise for myself — if you want to get better at something, practice! Second, to inspire those of you who might be in the same boat as me. And, finally, to help populate the internet with some leather jacket outfits for men that don’t look like what you see when you do that Google image search.

So here are six ways to wear five different leather jackets this winter.


Brown Suede With Shearling Collar

outfit idea with a suede bomber jacket and shearling collar

I would consider this the “grown up” version of that image search I’ve referenced. Swap the t-shirt for an OCBD, jeans in a more classic fit, suede chukkas, and suede leather jacket with a shearling collar. I have always felt that one of the best ways to dress casually when you get a little older is to wear something (or multiple things) in a more luxe material, like the suede you see here. It instantly elevates the look and gives the impression that you know exactly what you’re doing — even if you don’t…


Dark Brown Bomber, Part 1

how to wear a brown leather bomber jacket

One of the things I learned after going through this leather jacket styling exercise is that you can basically pair a leather jacket with just about any “normal” outfit you put together — including tailored clothing — so long as it is the right leather jacket. What you get when you hit it just right is a little bit of an edge and “cool factor,” for lack of a better term, to something that could seem just a little plain without it.

Take this look, for example. A classic (and exceptionally warm) fisherman sweater paired with some charcoal flannel trousers. It’s simple and doesn’t rock the boat. But add the leather jacket bomber jacket and throw on some Chelsea boots for good measure and suddenly there’s a bit more je nai sai quoi to the whole thing.


Black Bomber With Shearling Collar

how to wear a black leather bomber jacket

Here’s a variation on the last theme, this time with a black G-1 bomber jacket featuring a white shearling collar. I’ve really been feeling the darker grays and black thing this entire season. It’s easy. It always looks good. And it gives you a sense of confidence and mystery. It also makes it really easy to drop a leather jacket into the equation. What I really like about this particular combination is how it illustrates that you can wear, let’s say, a more sophisticated outfit with a leather jacket. Rather than looking like it doesn’t belong with a turtleneck, flannel trousers, and penny loafers, it adds a nice touch of sportiness.



outfit idea featuring a black and white varsity jacket

Alright, I hear you — the only thing leather about this varsity jacket are the sleeves. That’s enough for me, though! Consider this one a bit of a palate cleanser as it really is the most “generic” of the six looks we’ve got here. As much as I tried, nothing seemed more right than a simple and sporty styling with an athletic sweatshirt, light wash jeans, and good old white leather sneakers. Open to suggestions! Drop ‘em down in the comments.


Dark Brown Bomber, Part 2

outfit idea featuring a dark brown g-1 leather bomber jacket

One of the approaches I took when styling these leather jackets was to embrace aspects of the quiet luxury trend. Here, I’ve done that in two ways. First, the lighter color palette of the look’s foundation. I guess I don’t really need to understand why, but lighter colors almost always equate to a more luxurious look. It’s a thing. And second, some more luxe fabrics — a cashmere cable knit crew neck sweater and some suede split toe derbies, which tie into the color of the leather jacket quite nicely.


Black Suede Bomber

outfit idea featuring a black suede bomber jacket

Here’s another thumb in the eye for those who insist that, much like oil and water, black and brown do not mix. I’ve said it before and I’ll say it again: yes, they do! Of course, one must take into account the shades of brown and this outfit works because 1) there is a nice progression of light to mid-tone to dark and 2) the sweater against the black suede bomber does an incredible job of drawing your eye upward and framing my face — one of the keys to any well put together outfit. Don’t forget that!

The Bottom Line

I think the thing to take away from this post is that there are ways to style a leather jacket that aren’t rock and roll-influenced or overly sporty. Pair the right leather jacket with any outfit and — especially if you’re an older guy like me — you’ve just added a completely new dimension to your style.

Thanks, as always, for reading.

Stylishly Yours,

Brian Sacawa

Brian Sacawa is the Founder of He Spoke Style and one of the original men’s style influencers. Since 2013, his goal has remained the same: to provide men the advice and inspiration they need to dress well, develop their personal style, and gain more confidence. Brian’s interest and passion for men’s style and luxury watches has led to his writing for The Robb Report, The Rake, and Sotheby’s and he has been quoted on menswear in publications such as The New York Times, The Wall Street Journal,, Brides Magazine, and the Huffington Post. He lives in the woods north of Baltimore with his wife, Robin, kitties Nick and Nora, and German Shepherd/Collie mix Charlie.

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Edited by Rachel Butler

Photography by Rob McIver


Sometimes cocktails happen just because you taste something and know immediately what will make it better: 1/3 Grand Marnier with 2/3 Rosé Champagne (and, if I had it, a slice of grapefruit peel, or perhaps even better a dehydrated half slice - a dash of tonic sufficed here on the second).

It was whilst drinking this and considering what to watch on this Christmas evening that — after, discounting Metropolitan because I’ve watched it twice already, Trading Places, because I’ve watched it once, and then considering Die Hard (which is a favorite) — I realized that “Eyes Wide Shut” is actually my favorite Christmas film ever. So much so that I’m sitting watching it with my eleven year old daughter.