Whether you’re the kind of guy who meticulously plans his outfits or you prefer to improvise based on whatever isn’t buried in your hamper, there’s one article of clothing that’ll guarantee a sartorial confidence boost: the leather jacket. (A kickass pair of cowboy boots is definitely a close second.) With a leather jacket on your back, the mundane experiences of everyday life suddenly become moments to remember. You’ll be swaggering down the street instead of strolling. Sidling up to the bar for a top-shelf cocktail instead of the usual swill. And everyone around you will be thinking, “Who is that?” (In your head, at least.)

There’s no season better suited to a leather jacket than the cooler autumn and winter months. Need to get one in your closet? You’ve come to the right place. We’ve sifted through dozens of the latest and greatest leather jackets to zero in on our favorite pieces. Our wishlist hits on a variety of forms and variations, from bombers to truckers, that fit any type of occasion. And we’ve also highlighted the details that make them stand out from the pack—just like you will while wearing ‘em—including removable hoods, unconventional colorways, and more.

Schott dreamed up the original motorcycle jacket for Harley-Davidson nearly a century ago, but the legendary brand’s other styles are well worth a look, too. Inspired by workwear, this jacket is constructed with sturdy-yet-supple hand-buffed nubuck for superior style. It features a blue cotton chambray lining for added comfort, and details like a goatskin leather contrast collar and metal donut shank buttons really make it a standout.

Adding a killer leather jacket to your wardrobe doesn’t have to entail draining your bank account. Wilsons’ timeless Justin bomber is a premium leather jacket that’ll last a lifetime—and won’t cost you a fortune. It comes in five different colors (including a striking shade of blue), and over the years, it’ll fade and gain character the more you wear it.

This utilitarian overshirt is an outerwear classic and one of Valstar’s mainstays. It’s expertly handcrafted in Italy with super-soft lamb suede, and since it’s unlined, you can wear it through all seasons when you need a stylish layer that adds a pop of color. Fasten the button placket in the front or leave it open to reveal a graphic tee underneath.

Slick moto style meets bomber functionality with Overland’s Memphis jacket Biker Jackets. Made of top grain hand-waxed lambskin, it has a subtle sheen and a flattering slim fit, and its wool lining and removable knit collar and bib offer plenty of warmth. On the outside, key details like snap cuffs and a high collar with a buckle closure give it a distinctive look.

Inspired by vintage trucker jackets, this piece from Mr. Porter’s in-house menswear label is built for easy layering on cool-weather days. Sub it into any look you’d typically cap off with your favorite denim jacket—over a T-shirt or chunky turtleneck sweater, for example.