Purchasing a leather jacket for the first time can feel intimidating. They’re expensive, for one, and there’s always that nagging feeling that you might not be a “leather jacket kind of guy.” The process can be made easier, however, if you start by imagining what else you might like to wear with your jacket. Some look better with beat-up jeans and rugged boots, while others are more at home with tailored trousers. The type of jacket you’ll want to get depends on how you plan to wear it.
Rugged Looking Jackets
The most classic kind of leathers are flight and motorcycle jackets. They’re also the most rugged. For flight jackets, you’ll mostly find button-front A-1s and zip-front A-2s (the second of which is what you see above). For motorcycle jackets, there various iterations of double riders and café racers. These don’t have to be strictly utilitarian garments, of course. Many companies offer slightly more fashionable interpretations of these classics, but still retain that rugged feel. This RRL café racer, for example, is cut for guys who want to look cool while hanging out at cafes and eating croissants – not for guys who actually ride motorcycles.
You can wear such jackets with beat-up jeans and rugged chinos. Fatigues also work, although sometimes you risk going into cos-play. I pair mine with t-shirts and henleys, and layer a thick sweatshirt in if it’s chilly. Shoes can be almost any kind of rugged boot, although simple, pebbled grained chukkas are also nice.
Fashion Forward Jackets
By nature, fashion forward jackets can be hard to define, as they can take on so many different forms. The black, multi-zip jacket I have above, for example, is Maison Martin Margiela’s take on the classic café racer. Two big diagonal zips cut across the body, giving the jacket a unique appearance when worn. More avant garde designs can be seen from brands such as Rick Owens, MA+, and Julius. Tamer (and much more affordable) options can be found at APC, Golden Bear, and MKI Miyuki-Zoku.
Obviously, how you’ll want to wear your jacket will depend on exactly how it’s designed. For my Margiela jacket above, I mostly pair it with white or heathered grey t-shirts and black jeans. Shoes can be either black side-zip boots or minimalist white sneakers. You can easily swap all this out, however, for a white button-up shirt, thin grey sweater, and some charcoal wool pants for a slightly slicker look.
Dressy and Conservative Jackets
Finally, we come to dressy leather jackets. You can find these from companies such as Brioni, Canali, and Zegna, or more affordably at shops such as Brooks Brothers (think: where stylish dads shop). Being more conservative in design, these are often tame versions of flight jackets and cafe racers, and are made from soft lambskins instead of thick and heavy cowhides. As a result, you can more easily wear your jacket with tailored clothing, such as dress shirts and wool trousers. In fact, I think they look more at home with tailored clothes than they do with beat-up jeans and heavy workboots.
In the above, I have a dark brown moto jacket paired with some grey, glen plaid trousers, a pair of pebbled grained chukkas, and a light blue, oxford-cloth button-down shirt (which would be worn tucked in). The nice thing about this outfit is that you can swap the jacket out for a sport coat if you want an even dressier look. This is great if you’re traveling and need to transition from business to nights out with very little in your luggage.
