I bought my first leather jacket at a vintage fair in an old English cathedral. I was 19, and a middle-aged British lady told me I looked good in it. Clearly a sales technique, but it worked, and I shelled out my grocery money for it.
I had grand plans of fixing up my dad’s old Honda the following semester and riding around campus in a sick jacket. For various reasons, that didn’t end up happening, and I ended up on a 50cc Yamaha Zuma, a fun little scooter but one where a creaky moto jacket looked more like a comic prop than something out of a Dennis Hopper film. C’est la vie; we all look a little ridiculous in our 20s.
Despite what cinema tells you, you don’t need to ride a motorcycle in order to wear a leather jacket. Or fly a WWII-era fighter plane. Or be Steve McQueen photographed for Esquire.
Leather jackets are imbued with the undeniable cool factor of their original functionality—like work jackets, chore coats, and waxed canvas, the modern menswear landscape supports multiple usages. From happy hours to midwestern winters to, yes, actually riding a motorcycle, we’ve rounded up nine Esquire-approved picks to guide your foray into the iconic outerwear. And to come full circle, I did actually test some of these on a motorcycle.
More than a decade later, I finally got my license and am fixing up that old Honda; thank God for YouTube. Leather 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.
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