Every guy knows that a leather jacket of some kind is a timeless cold-weather must-have. Whether you’re layering over a hoodie or t-shirt to edge up your casual everyday look, or over a sleek button-down shirt to roughen up your night-out or biz-casual outfit, a leather jacket can totally make, break, or switch up your outfit. And while there’s normally plenty of styles and fits to choose from, this season is all about the leather bomber. And yes – that still leaves plenty of possibilities to explore, but that’s where you own personal style comes in to help narrow down the perfect leather bomber for you. If you’re looking for something sleek and streamlined to show off your frame, something fitted like this Rick Owens Zip Front Bomber from Barneys has a cool incognito look going on. Speaking of incognito, if you’re a guy who likes to lay low (or just accessorize) with a hood, this Dolce & Gabbana jacket’s got you covered, plus has some cool added texture with its wrinkled effect. And of course, if you prefer something a bit more relaxed and laid-back, this Ralph Lauren Purple Label Bomber Jacket stays roomy without looking sloppy.

- Alexandra Gambardella