The 10 Leather Jackets You (Yes, You) Could Actually Pull Off

Every product was carefully curated by an Esquire editor. We may earn a commission from these links. Here’s how we test products and why you should trust us.Nili Lotan/AYR/OverlandLeather jackets can be tricky to get right. Too trend focused and it’s a thousand-dollar flash in the pan; too trend agnostic and you get a museum artifact rather than a wearable piece. Ayr nailed the balance on its cleverly named Scrambler jacket, which draws on moto history and sits in the Goldilocks zone between classic and contemporary.I’ve worn it motorcycling through the Appalachian mountain roads and plan on packing it for an upcoming jaunt to Europe. If you’re looking for a more classic moto style, I also own and highly endorse the elegantly named Baby Grand. The brand (and menswear lead Brice Pattison) has the Midas touch of outerwear; every style is worth its weight in gold.Features at a GlanceSure, there are excellent (and expensive) picks from Loewe, Celine, and Tom Ford with extra-premium materials, brand-specific takes on classic silhouettes, and the extra designer oomph that makes them worth it in some circles. But in this price range, I’m more interested in the experimental and new perspective of a brand like Stòffa, which you can tell is having fun with fabric and silhouettes. This Wave Leather jacket somehow manages to be sleek and drape-y all at once. A daydream of a jacket that’s definitely pricey but somehow still more affordable by half than other designer pieces out there.Features at a GlanceAdvertisement - Continue Reading BelowBudget leather goods can be problematic. Under a certain price threshold, you’re almost certainly not getting the real thing, in which case you’d be better off going with a disclosed imitation-leather piece from the likes of all-star mall brands like Banana Republic and Abercrombie & Fitch. Or eBay, where a tape measure and a search for Wilson’s Leather or vintage Orvis will unlock a treasure trove of perfectly patinated jackets. For brand-new on a budget, I recommend the Jacket Maker. Its cut will be a little less forgiving than those of the pricier brands in this list, but if you’re a guy who fits well into off-the-rack suits, you shouldn’t have an issue. Plus, the brand offers a custom, made-to-measure jacket-design tool that has me tempted to re-create McQueen’s from The Great Escape. Features at a GlanceMaterial100% Sheepskin LeatherThis is the one on this list that takes the most bravado. This is the one that upon first wear will get you some looks for your usual drinking buddies. And with good reason—a Schott Perfecto is a loaded garment. Marlon Brando, James Dean, the Ramones, and any cool guy that’s worn one before are not easy acts to follow. But if this is what the heart wants, we stand behind you fully.The key is in how you wear it. Crucially, you should not “style” it. You should pick it up as much as possible and wear it with as many disparate collections of clothes as you can. For the first few weeks, you might be seen as “The guy trying to wear a leather jacket.” But after a month or two, that will turn into “The leather jacket guy.” Wear it hard, wear it proud, and wear it everywhere.And one note on the type of leather. If you’re buying new, we think you should go for horsehide. It’s the toughest of the bunch and takes the longest to mold to your body, but that makes it fun.Advertisement - Continue Reading BelowA shearling jacket is hard to pull off in day-to-day life. Done incorrectly, it can quickly devolve into a kind of cosplay of a WWII fighter pilot. Overland’s Lance jacket retains the genuine sheepskin lining but softens the look with a handsome dark navy colorway paired with a more subtle brown lining, giving you the warmth and badassery without crossing over into costume territory—unless that’s your thing, in which case the brand’s B-3 bomber re-creation is right up your alley. (Though, as always, Todd Snyder’s take is more wearable.)Features at a GlanceMaterialSpanish SheepskinI want every leather jacket to have an origin story like Taylor Stitch’s, which begins with one of the brand’s designers re-creating a beloved café-racer-style jacket his dad bought in the ’70s and wore to perfection. It turns out the original manufacturer, Golden Bear, was around the corner from TS, and the two brands worked together to reissue the style. It’s got some modern twists like a Thinsulate lining but retains the design cues that make it functional on a bike and just plain cool on its own. I’ve coveted this jacket for years and recently got my hands on it IRL, and, boy, it does not disappoint. The Whiskey Steerhide colorway looks a little early-aughts coded online, but in person it looks like the magic liquid itself: golden and invigorating. For a non-insulated, more lifestyle-oriented take on the silhouette, I’d point you to Billy Reid’s Blake jacket, which is my dive bar go-to.Features at a GlanceMaterial3.5oz Full-Grain SteerhideAdvertisement - Continue Reading BelowRough out has the wearability of suede, and doesn’t look as turbo as smooth leather. But unlike typical suede, which splits the original hide, rough out retains the whole of the hide. That makes it just as durable and water-resistant as any other leather.Add that to Billy Reid’s Blake rider shape, and you get a jacket that any guy—literally any guy, we swear—off the street could toss on and feel good in.Look, the whole oversized vibe is cool and all—but we’re also keenly aware it doesn’t work for everyone. Sure, it brings that chill, relaxed vibe. But sometimes you can just end up looking like a kid wearing their dad’s clothes. If you’re looking for something that hugs the body a bit more, opt for Mili Lotan’s Hammond jacket. It’s got enough slouch you could wear a few layers beneath, but will flatter the body a little more than some of the other options on this list.Features at a GlanceMaterials100% calfskin leatherAdvertisement - Continue Reading BelowI am big on brands that care about details and let the clothes speak for themselves. Octobre Éditions is one such brand. The cut and the cloth set the clothes apart and create longevity outside the trend cycle. When you’ve designed a perfect OCBD, you can never really go out of style. Same too with the brand’s excellent Larren jacket, which I have and is unfortunately currently OOS. Thankfully, the Peylor cuts the same silhouette in a nubby split leather that I’m a little envious of. Get it while the getting’s good.Features at a GlanceMaterial100% Bovine LeatherThis is a dream leather jacket—the sort of thing you’d have on a list of “Things I’d Buy If I Had All The Money In The World.” It’s rugged, it’s suave, and damn is it comfy. Just looking at that sumptuous shearling tells you this is a jacket you’d never want to take off, especially on those brutal winter days.Features at a GlanceMaterial100% lamb leather and 100% shearlingAdvertisement - Continue Reading BelowWhy trust Esquire?Our editors spend a lot of time assessing what’s in, what’s cool, and what you should care about. It’s literally part of our whole job. Sometimes that means trying things out first-hand, sometimes it’s about thorough research, and sometimes it’s just something you know. Whatever the means, we’ve done the work to figure out what is and isn’t worth your time and money.