27 Timeless Leather Jackets to Wear for the Rest of Your Life

There’s no way around it: A good leather jacket is as much of a cold-weather wardrobe staple as a pair of all-weather boots or chunky scarf. The easy outerwear style is the perfect go-to topper for chilly, transitional-weather days, but as the weather gets truly frigid, it also makes a great layering piece. And though the classic moto is usually the silhouette that comes to mind, other iterations—like blazers, trenches, and shackets (a shirt-jacket)—have taken the spotlight lately, too. 

No matter which silhouette you go for, the best leather jacket is inherently edgy. Whether you wear it with straight-leg jeans and a t-shirt, or over a maxi dress, the right one will lend a touch of sophistication and insouciance to any outfit. Even better: If you do enough research, it’s a piece you’ll only have to buy once. Ahead, we've rounded up the 27 best leather jackets that will last a lifetime.

Leather Moto Jackets

The classic moto jacket has remained more or less the same silhouette since Schott NYC first debuted the Perfecto in 1928. A modern moto jacket is slim through the shoulders, has high-cut armholes, and hits your hip. But if you’re looking to layer a lot underneath, opt for a slightly roomier fit in the arms. Subtle details like snap-button epaulets, sturdy hardware, and proportionate lapels are a dead giveaway that yours will stand the test of time.

Leather Blazers

There’s a good chance one of your parents owned a leather blazer in the '80s or '90s. Anyone who wore one—likely with a pair of light-wash jeans and lace-up Keds—was an absolute paragon of style. The same holds true today, and though a leather blazer might seem like a difficult item to style, it’s more wearable than ever. Look for an appropriately oversized one: a boxy fit is best. If you prefer one that cinches at the waist, size up for a more relaxed look. Then, treat it more like a blazer than a leather jacket. Pair it with roomy trousers and sneakers for a true '90s vibe.

Leather Trench Coats

The leather trench was one of last fall’s most interesting breakout trends, and it’s not hard to see why. Not only is a leather iteration warmer than your classic gabardine trench coat, but it easily becomes the spotlight of any outfit. Pair yours with knee-high boots that hit right at the hem of the coat, or wear them with a pair of logo tights and brogues for a menswear-inspired look.

Faux Leather Jackets

There is a myriad of reasons to opt for a faux leather jacket. For one, there are so many materials that look exactly like the real thing—and they’re usually a touch less expensive. Either way, SJYP’s iteration, with its vegan sherpa lining and pin-buckle details, will quickly become your most memorable winter jacket. On the other hand, Source Unknown’s vegan belted blazer pairs well with everything you already own and looks even more expensive in reality. 

Leather Shackets 

The shacket is a hybrid of a shirt and a jacket. It’s a must-have during the winter months, no matter if you’re wearing it alone or as a layering piece. LVIR’s faux-leather version toes the line between shirt and jacket. You can wear it belted at the waist with a pair of crepe trousers or let it hang loosely under an oversized longline coat. Nanushka’s iteration, however, has mid-length sleeves that are practically begging for a thin-knit turtleneck underneath.