Pick a style.
While there are many different styles of leather jacket, we're partial to these three classic cuts because they're both comfortable and flexible – you can wear them anywhere. The same cannot be said of the longer leather duster.
Motocross: On the racetrack, a reduction in the slightest bit of drag can mean the difference between celebrating in the winner's circle and treating a serious case of road rash. It's out of this need for speed that the motocross jacket evolved. Fitting snug, this style hits low at the waist, hugs the shoulders and torso, and often includes a strap that buttons around the neck. If you're a thinner fella or just looking for a good jacket to pair with a café racer, a motocross is a good bet. [Leather Biker Jacket; LevisMadeandCrafted.com]
Fatigue: Descended from standard-issue military gear, the fatigue jacket can be easily identified by the dual chest pockets and robust shoulder reinforcements. A versatile article of clothing, the fatigue style (above, in brown) looks sharp no matter whether it's paired with a shirt and tie or your beloved Neil Young concert T-shirt. [Belstaff Panter Jacket, $1995; Belstaff.com]
Bomber: During World War II, advances in aviation technology sent heavy bombers to altitudes of 25,000 feet and higher. Typically these aircraft were neither pressurized nor insulated, and crew members had to wear heavy, sheepskin-lined leather jackets in order to endure temperatures that dipped to 58 degrees below zero. Today, a bomber jacket (above) can be purchased sans sheepskin, but there are insulated versions if you want to stay warm in cold climates. If you're a bigger guy, the bomber's shape will likely flatter your physique. [Orvis Spirit Leather Flight Jacket, $375; Orvis.com]