The obvious: You’re going to need a jacket this fall. After all, autumn is undeniably the best season for light jackets—the bitterness of winter is still far enough away to justify a non-down option, but the crisp mornings and chilly evenings mean that an extra layer is all but required. The slightly more difficult question isn't so much about what as it is about which. From anoraks to zip-ups, car coats to work jackets, there's an outer layer for everyone these days, and sometimes, that can feel overwhelming.

The season's best vary in shape, size and style, but all share one thing in common—enough protection to keep you warm and look great while doing so. With so many styles to choose from, you can pick the jacket best for your personal dress code, but some of our favorite looks of the season involve defying expectations. Matching a longer, dressier coat with sweats is arguably the ultimate way to do high-low in fall 2021, when even a refined gent can get away with a hoodie. Likewise, a sleek nylon bomber or zip-up over a shirt-trouser combo has been a go-to look for some of Valet.'s favorite dressers for some time now. The best jackets should have something special, because if there's any time to let your outerwear do the talking, it's now.