Men had been wrapping themselves in animal skins for centuries before World War I fighter aces devised the leather jacket as a way to combat freezing temperatures at high altitude. Over the years, the pilot's necessity became a mark of rebellion for bikers and a statement piece for ascendant rock stars.
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These days, a leather jacket is no longer a specific signifier, which means that every man can have one and wear it every day – it is, after all, one of the most versatile pieces of outerwear available. Throw it over a T-shirt and or dress it up with a tie. The options are myriad and it's hard not to look slick.
Still, with countless menswear companies making hundreds of different models in a variety of cuts, actually buying a leather jacket can be quite complicated. But it doesn't have to be. Follow these steps to find a jacket that will fit your torso and your personality.
Consider how you’ll wear it.
Every leather jacket buyer has his own agenda. A lot of guys are looking for something they can wear out to bars and clubs. Others are looking for a piece of outerwear to throw on every morning. The important thing is to know which look you want.
The Rocker Look: Your leather jacket should pair well with an undershirt, the shirt you wear while changing the oil in your car, any shirt you wear to a concert, and – if you really want to go for it – a fitted henley. As long as you avoid shirts emblazoned with the words "No Fear" or energy drink logos, you'll end up looking ready for a night on the town without appearing to be trying too hard.
The Professional Look: Pairing your leather jacket with an oxford shirt and tie can be tricky, but it's not rocket science. Just consider whether your wardrobe is well suited to a tighter-fitting jacket. You'll want narrower shirts and skinnier ties. A bow tie isn't going to work and neither are pleated khakis. You don't want to look like your torso is rebelling against your legs. Keep in mind that this is never going to be an acceptable outfit to wear to a board meeting unless you work at a successful record label.
The Downtown Look: If you pair a leather jacket with torn denim then smoke eight cartons of cigarettes a day for three weeks, you can look like Iggy Pop, circa 1973. That's fine, but we'd recommend sticking to dark, narrow, and tear-free jeans. Do not attempt to wear "Dad jeans" with a leather jacket. Romney lost.
The AC/DC Look: You could wear your new jacket with shorts. Please don't.
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