The Best Men’s Chelsea Boots to Wear This Fall

This slip-on boot style can be rugged and dressy all at once.

New Republic

As the leaves turn and a breeze picks up, perhaps you’re hearing a different sort of whisper carried on the breeze. It’s your boots and your flannel shirts, beckoning you to start wearing them again as often as possible. While lace-up dress boots and classic chukka boots belong in your rotation, you’d also do well to stock up on at least one — no, more than one — variation of the best Chelsea boots.

Chelsea boots take many forms, from sleek, dressier suede boots to rugged, everyday pull-on boots that are closer in form to work boots. It’s worth exploring multiple options though, all the better to wear with everything from tailored trousers (dressy Chelsea boots) or selvedge denim (hard-wearing, workman-like pull-on boots). Here, some of the best Chelsea boots to wear right now. 

Hari Mari Waxed Odessa Boots

Hari Mari

Hari Mari is best known for its finely made leather flip-flops, but they’re upping the ante with a pair of fall-ready waxed suede Chelsea boots. That treatment makes them wearable in plenty of different fall style scenarios, especially in a rich tan color to pair with faded blue jeans and a thermal henley. $165

Blundstone 585 Classic Chelsea Boots


These Blundstone boots are aptly named and truly a timeless fall style move, built with plenty of durability and shock absorption. They’re easy to pull on for day hikes and brewery hopping, and you’ll find them in stylish neighborhoods from the Pacific Northwest to Brooklyn and beyond. If you’ve never tried a pair, you might just find that once you start wearing them, they’ll be on your feet every single day. $199.95

New Republic Sonoma Suede Chelsea Boots

New Republic

Serving as one of the dressiest and cleanest designs on this list is New Republic’s Sonoma silhouette. The form-fitting suede and leather construction hugs the foot without causing discomfort right out of the box—no break-in period necessary. A neutral six-color palette ranging from tan and sandstone to chocolate and natural black facilitates pairings with virtually any tailored trouser or upscale jean. And thanks to the digital brand’s site-wide sale, you can have the Sonoma for a bargain. $89.50—Brandon Friederich

Kodiak Bruce Chelsea Boots 


Chelsea boots are an ace fall footwear option for several reasons, chief among them being the fact that you can wear the right pair almost on the daily. With waterproof leather and a handsome tan colorway atop a rugged black treaded outsole, these fit the mold perfectly. Style them with blue jeans and a flannel shirt, or else wool trousers. $160

Wolverine BLVD Chelsea Boots


Thought Wolverine only made work boots? Think again, because these Chelsea boots manage to be both refined and rugged, all at once. The full-grain leather will only get better with age, the sheepskin lining offers all-day comfort and the rubber lug outsole delivers grip and yet a relatively low profile. Wear them with chinos, black denim or wool trousers with ease. $199

Florsheim Foundry Plain Toe Gore Boots


Florsheim really takes things up a notch with these handsome, old school-inspired Horween leather boots. They’re created in  a nod to rugged leather boot styles of decades gone by, built with a durable rubber sole and a low profile that works at the office or on an upstate getaway. $260

Taylor Stitch Ranch Boots

Taylor Stitch

The good folks at San Francisco-based Taylor Stitch turned to boots worn throughout the Old West to fashion these remarkably dependable, workman-like pull-on boots. Team them with a navy wool suit or else wear ‘em with grey selvedge denim to grab a cold, cheap beer on a cool fall night. $348

Red Wing Heritage Weekender Chelsea Boots

Red Wing

If it’s unstoppable comfort and rugged appeal that you seek, Red Wing Heritage always has your back. These richly crafted leather boots are ready for early mornings in the yard or late nights at a whiskey distillery, with all the value you could ever want in your next pair of Chelsea boots. $239.99