When it comes to outerwear, few styles come pre-loaded with as much meaning as a shearling. Not too long ago, the mere mention of it evoked images of the Marlboro Man. Those long, bulky, no-nonsense coats that have patchwork seams running up-and-down the back, and tufts of wool peeking out from beneath the cuffs. The silhouettes are blocky; the leathers often dry and cracked. They make their wearers look like King Kong.

There have been times, however, when shearlings were considerably more luxurious – even if questionable in taste. In the early 1930s, catalog retailers advertised shearling coats alongside suede leather jackets and horsehide outerwear, seemingly unaware of the Great Depression. The material came roaring back in the ‘70s with the Peacock Revolution. Swanky men wore them with chunky turtlenecks and velvet bellbottoms, presumably to their eternal regret years later. They’ve also been part of some important rebel uniforms, including the better side of skinheads (e.g. the non-racist kind) and French zazous (who were an anti-establishment, punk version of French dandies).

Shearlings are back again, and I think it’s due in no small part to the porousness between men’s and women’s fashion. Whereas dressmaking and tailoring used to be two separate trades, designers across the aisle today freely take inspiration from each other. Phoebe Philo, for example, is credited as being a feminist for how she makes women feel comfortable in their own bodies. When she recently stepped down as the Creative Director at Celine, Vanessa Friedman at The New York Times described her clothes as being for the “grown-up woman.”

Ms. Philo was interested not in what would attract the male gaze, but the female gaze (I can’t tell you how many shows I left with male colleagues who were shaking their heads and saying, “I just don’t get it,” while all the women in the audience were making fantasy shopping lists). And even more important: the grown-up female gaze. And in her clothes — deep pile, no-nonsense, swaddling, streamlined — many of them recognized themselves.

Philo never made a menswear collection, but her impact can be felt in many male wardrobes. Stan Smiths? She was one of the first to co-sign them. Vans slip-ons? She helped bring those back with a luxe version of the skate shoes. Birkenstocks and slides? An early endorser. This ugly shoe moment? Her too. Pajamas as daywear? Yes. A loosening of silhouettes? Her style signature.

Similarly, before Balenciaga started churning out the fashion equivalent of Spencer’s gag gifts, the label was one of dreams and beauty. Led by Nicolas Ghesquière, a self-taught designer who took over at the incredibly young age of 25, the label was known for its contrasting silhouettes – slim, high-waisted trousers paired with voluminous coats or rounded jackets (sound familiar?). One of Ghesquière’s more famous pieces is an curly-haired, shearling aviator, which came in dark, moody colors such as slate gray and black. He didn’t invent the design from whole cloth, of course. It’s inspired by the sheepskin jackets American male pilots wore during the Second World War.

Shearlings have been bubbling in the menswear cauldron for a while, but they’ve really come into their own this season (I credit this moment as the tipping point). Mr. Porter even has an entire section dedicated to the style this winter. And while they’re expensive, many aren’t that much more than a normal leather jacket (expect to pay somewhere between $1,000 and $2,000). The real cost is in the maintenance. Since shearlings are closer to fur coats than regular leather jackets, you have to take them to a professional cleaner – a competent specialist who knows how to deal with the material. Expect to pay a couple of hundred bucks per cleaning.

On the upside, shearlings are fairly rugged, even in inclement weather and despite their soft surface. If the jacket gets a little wet, causing spotting or streaking, hang it up to dry in a well-ventilated room and away from direct heat. The next day, brush it out with a soft-bristle brush or dry sponge. Then with a clean cloth, brush it again in the direction of the skin to smooth it out. Darker shearlings will hide soil and stains; rugged designs may even look better with a weathered patina. If you’re really worried about it, you can wear a scarf around your neck to keep the leather from being soiled by your skin.

I like shearlings in more rugged styles – something you can wear with slim jeans and boots, maybe with a textured sweater or even just a t-shirt underneath (the fleece acts as knitwear anyway). Certain designs can also worn with wool trousers for a more contemporary outfit. Some models I’ve been looking at:









Valstar: A classically cut trucker made from a wonderfully spongey shearling. Easy to wear, handsome, and the sort of thing you can throw together with jeans and flannel shirts. I also like how it looks layered over thin, wool turtlenecks. One of my favorites this season. Available at No Man Walks Alone, a sponsor on this site, and Mr. Porter.

James Grose: Another favorite. I’ve been waiting for this model all year and it just dropped at No Man Walks Alone. I usually wear a size 38, but think this might look better slightly oversized (I just bought a size 40). Given that it’s an all-black jacket, I think it’ll look more at home in all-black outfits – black jeans, black boots, and black sweaters. Something different from the usual double riders you see everywhere.

Todd Snyder: Two great styles this season that include a bomber and trucker jacket. I like the cleaner look of Valstar’s trucker design, but appreciate the side-entry hand pockets on Todd Snyder’s version. The bomber jacket, on the other hand, simply looks perfect. It has a generously sized collar, storm guard closure, and adjustable side tabs. The silhouette again looks good without being challenging to wear.

Cromford Leather Company: Cromford of London offers bespoke, made-to-measure, and ready-to-wear leather jackets in slightly more traditional styles (although I think more wearable than Cockpit). My tailor/ coat-maker at Steed thinks Cromford produces some of the best leather jackets around. This season, they made two shearlings for Division Road and The Rake (both sponsors on this site). The first comes in a dark slate gray leather; the second is in a more traditional brown-tan combination. The first can be worn with raw denim jeans for an updated workwear ensemble, while the second might be better for a classic casual look.

The Armoury: A great in-house design by The Armoury that was inspired by a sheepskin Alain Delon wore in the film Once a Thief. Like many of Armoury’s more casual offerings, this one is made so that you can wear it on its own or over tailoring. The collar was made a bit bigger; the body was lengthened to cover a sport coat. I like how it’s presented in The Armoury’s new Upstate lookbook.

RRL: This grizzly jacket isn’t for everyone, but if you’re into heavy denim and engineer boots, nothing else will do.

Joseph: A little more fashion forward, this Joseph jacket is distinguished by its olive green body and white lapels. It’s a little too aggressively fashionable for me, but it could suit the right personality and lifestyle.

Karl Lagerfeld: Forever thoughtful, Karl Lagerfeld was nice enough to design a $300 all-black shearling for your goth baby.

President’s: The cool thing about this “university” shearling is its texture. Not only is it a piece of outerwear, but you can also use it as an absorbent bathmat. If you buy this, you have to use an extra-long bath rug as a scarf (sorry, I don’t make the rules).

Levi’s: Not technically a shearling, but Levi’s sherpa jackets are affordable and lend a similar look. You can also get them second-hand for under $100. If you’re afraid of the denim-on-denim look, try a tan sherpa with blue jeans or a blue sherpa with black jeans. Just note that some of the older designs have really rounded bodies, which may or may not be your thing.