When it comes to stylish essentials, the denim jacket pretty much tops the list. The very definition of a staple, it's the kind of works-in-any-situation piece that will never let you down. Which is likely why you and every guy you know owns one. Whether dark and crisp or washed and relaxed, slim-cut or oversized, it's a jacket that is flattering at every age and will forever remain cool. But, who says you should only own one?

This is one of those rare garments that can be worn all year long, in the morning or in the evening, with a T-shirt or with a tie. And when it's really cold out, layer it under your bigger coats or even under your corduroy or tweed blazers. Wear it however you'd like, because you see, when you pull on a jean jacket, you instantly get a shot of badass style, because you can't separate the jacket from its rich history—the cowboys, bikers and punk rockers who've all worn the jacket before you. These days, they come in all sorts of iterations, so you can easily have more than one. From classic truckers and distressed vintage-inspired options to more modern interpretations, here are the season's best options to consider adding to your collection.