Buying a leather jacket can be a daunting task. Like almost everything else these days, there are leather jackets for every budget and every style. But there’s a reason for that: Pretty much every list of menswear essentials includes at least one leather jacket. It’s one of menswear’s foundational pieces, having been worn for decades and tied to some of the icons of men’s style.

The right leather jacket will last you years. Leather goods—at least high-quality ones—get better with age. Like denim, they’re moulded by how you wear them; they take the shape of your body and develop details and quirks that are unique to how you use them. But, more important than just being durable, a good leather jacket stands up to trends; it won’t just last you more than a decade—it won’t look out of place.

That makes choosing the right jacket supremely important—it’s not hard to buy a great leather jacket, but it’s easy to buy a dud. But why settle for a dud, or a series of duds, when one shrewd investment can land you a foundation piece of your wardrobe that you’ll wear for years to come… and maybe even pass on to someone else down the line.

The beauty of premium leather jackets is that you don’t really lose anything by not buying them new—the best jackets can be bought second-hand. While this is by no means exhaustive, these 20 leather jackets represent about as good a jumping off point as possible if you’re looking to buy a leather jacket for the first time—or simply looking to take your jacket game to the next level.

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Lead image via Complex.

How Should a Leather Jacket Fit?

A leather jacket has a unique fit criteria and characteristics. Somewhere between a shirt jacket and heavyweight outerwear, the best leather jackets will fit your body comfortably on the shoulders and will fit snug around the underarms (armpits). The general rule for outerwear is to air on the roomier side in order to accomodate thicker sweaters and layers that will naturally be worn during cooler temperatures. In this case, the classic style is keep a leather jacket a little more fitted; you should be able to wear a lightweight knit underneath your leather jacket. While there are a variety of different leather jacket silhouettes in the market, the classic “motorcycle jacket” or leather bomber jacket should land at your waistline—if not right where you would wear a belt.

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