The 18 Best Jackets to Wear This Fall

When the weather drops and the air is crisp, nothing finishes off a fit for fall quite like the best jackets. (Ditto fall coats.) They not only insulate, but, more importantly, impart a sense of self. Take, for example, James Dean in Rebel Without Cause. The iconic cherry-red windbreaker he wore in the angst-fueled teen flick conveyed a lot about his character. He was an outsider, standing out amongst the sea of black, brown, and blue that his peers wore. He outwardly spoke—even cried—about yearning for acceptance, but his id and his impulses, as demonstrated by his eye-catching jacket, proved otherwise.

Yes, I am waxing philosophic in a round-up of the best fall jackets. I tend to do that sometimes, but, dear reader, no lies were told. The type of topper you wear lets people know the kind of guy you are—or might want to be—from the jump. It’s the first impression and, oftentimes, the lasting one. So, before you reach for any ol’ thing, make sure to pick the style that is right for you. Because, as you can imagine, the options abound.

From bombers in every conceivable fabric and anoraks in a spectrum of colors to field and motorcycle jackets with the same scope, you have the ability to tell your own story concisely with a single item. If you’re a rebel, take a page from Jimmy Dean and opt for a bright windbreaker. Are you artistically inclined? There are a slew of jackets with eye-catching prints or appliqués. But if you’re more laid-back dude, denim or a classic coach's jacket will do nicely. To help narrow down your search, we corralled some choices—all of them great, all of them perfect for fall, and all of them telling.