Truly, the Greatest Winter Coat of All Time

SHOP $695, overland.com

Welcome to the Esquire Endorsement. Heavily researched. Thoroughly vetted. These picks are the best way to spend your hard-earned cash.

Newsflash: Just because it’s cold as hell outside doesn’t mean you have to sacrifice your style to stay warm. In a sea of black puffer jackets and parkas, be the guy whose outerwear is actually fashionable. The guy who knows how to find a piece of clothing that enhances and elevates his look, rather than covering it up. The guy with a staple statement jacket that’s easy to reach for, throw on, and go. To be that guy is simple—you just need the Overland Classic Sheepskin B-3 Bomber Jacket.

Trust me on this one, ’cause I’m picky about my jackets. I live in New York, where the winters are cold and harsh, but even a day full of snow, hail, and a squall isn’t a valid excuse to skimp on style. Dressing for warmth and for looks is a trick that not everybody has mastered, but honestly, I have. And the B-3 bomber is my ultimate secret weapon. I’ll never so much as shiver outside, and I’ll never meet the even worse fate of being underdressed, either.

SHOP $695, overland.com

It has timeless style

This is a jacket that hasn’t gone out of style since World War II, and I don’t expect it to go out of style anytime soon. It’s the very definition of timeless. In a world full of ever-changing micro-trends that don’t even last one season, this is an icon with a look that’s pervaded decades. Equal parts rugged and chic, this is how you brave winter with ease (and with that cool “Austin Butler in Masters of the Air” look). The B-3 comes in a rich, dark-brown, napa-leather option with cream erino sheepskin, or a black napa-leather option with black merino sheepskin. You can’t go wrong with either, but in my books, the brown-and-cream one exudes a classic yet cozy vibe and highlights the details and features of the bomber better.

No matter how you wear this jacket—and there are a lot of ways to wear it, which I’ll get into in a second—it looks fan-fucking-tastic. It’s suitable for every man’s taste and style. It’s easily dressed down with a pair of jeans and a Henley shirt and sneakers or dressed up with pleated trousers and a button-down and dress shoes. This is going to be your go-to winter coat for every occasion, because, honestly—I know nothing else in your closet looks and performs this well. Nothing in my closet does, at least.

This jacket comes in Standard, Short, and Tall lengths, so you’re guaranteed to get one that fits and flatters you well—don’t worry about spending a ton of money on a jacket that won’t fit perfectly, because this one will. (The brand recommends Tall fits for men who are over six feet and have long arms and Short fits to those under 5’8″). Even though I’m 5’3″, I wear the Standard fit because I like an oversize, long length that reaches my thighs, but whether you size up or stay true to yours, this jacket leaves enough room for comfortable layering underneath—not that you’ll need to layer up that much, though, given how damn warm it is.

SHOP $695, overland.com

The quality—and warmth—is unmatched

Here’s something to know about Overland: The family-run brand has been manufacturing sheepskin coats since 1973, when it first started hand-sewing them out of New Mexico. Do you know what that means? It means that, over 50 years later, the brand is pretty damn great at making sheepskin coats. One wear of the B-3 bomber is sufficient evidence that Overland has mastered the craft.

These days, production of the B-3 bomber has shifted out of the U.S. and into Turkey, where every coat is crafted by trained artisans. This isn’t your average factory-made jacket that’ll have a broken zipper and split seams within a few months. It’s crafted with the highest quality that you can see in every detail and feel with every wear. Literally—the coat does weigh almost six pounds. You can feel the quality in the heaviness—this isn’t your cheap, lightweight, polyester winter jacket. It’s pure leather with sheepskin lining, and it’s weighty. How’s that for hardy and durable?

Even though this coat might cost more than you’re used to spending, it’s a one-time buy for a lifetime of wear, baby. The price is reflected in the quality of the coat, which will absolutely keep you warm all winter long. Originally, B-3 bombers were crafted for American fighter pilots during WWII, to keep them warm when they were 30,000 feet above the ground. Although the look of the B-3 has been slightly modernized since, that same sentiment and technology has pervaded; this is still warm and cozy as hell. The bomber has been temperature tested and has a temperature rating of 1°F, so even when it’s really freezing, you’ll be toasty.

To make sure it wasn’t just a super-cold-weather coat, though, I’ve been putting my bomber to the true test of whether it can withstand shifting temperatures by seeing how it holds up on the NYC subway system. When I’m on a super-warm, non-air-conditioned subway platform or train car, I still don’t feel overheated in this jacket; it’s surprisingly breathable and easily adapts to changing temperatures.

SHOP $695, overland.com

And it’s packed with functional design details

A coat that simply keeps you warm and looks good while doing it isn’t enough. It’s gotta go above and beyond with features and functions that are convenient, too. Overland’s B-3 bomber is up to the task.

The jacket has a detachable hood (which is also luxuriously lined with plush, supersoft sheepskin) that effortlessly zips on and off for versatile wear. There are also leather buckles at the collar that you can adjust for a high-neck, fully zipped-up look. For me, this jacket is all about those small details: the white contrast stitching at the seams, the soft distressing of the leather that gives it a pre-worn look and feel, the adjustable leather buckles at the hips that can give you that perfectly tailored look.

And if you, like me and any other rational person, require deep pockets that are perfectly placed so you can stuff your hands in ’em, I’ve got good news for you—the B-3 has two slant pockets on the outer designed to do just that. There’s an additional pocket on the inside, too, which I find convenient for storing my phone when it’s so cold outside that I’m worried it’ll literally freeze.

Truly, the B-3 is a gift to yourself for years to come. If you get it for someone else, it’ll be the best gift they’ve gotten perhaps ever. And since it is gifting season, after all, ’tis the time to score one.

SHOP $695, overland.com

Photographs by Joe Lingeman. Prop styling by Heather Greene.