Amp Up Your Fall Footwear with the Best Men’s Chelsea Boots

Classic Chelsea Boot Huckberry

Want the ultimate in “cool guy” style? Step into a pair of the best men’s Chelsea boots — the right pair can go a long way in terms of a simple-yet-crisp footwear upgrade as we head into fall. While we’re all about stylish sneakers and even classic suede chukka boots for the spring and summer, there’s something pleasingly substantial and tough about a pair of the best men’s Chelsea boots. With equal parts rock-ready edge and sleek style, the right pair of Chelsea boots looks great peeking out from slim black denim or a tailored worsted wool suit in equal measure. We hope you’ll agree — oh, and here are our picks for the best men’s Chelsea boots to get you started.

Allen Edmonds Liverpool Chelsea Dress Boot, $445

Allen Edmonds Chelsea Boots

Chelsea boots tend to call mind rock icons of years gone by — the Beatles didn’t step out in Chelsea boots with drainpipe trousers for nothing, after all. Allen Edmonds’ Liverpool Chelsea Dress Boot nods to the past while boasting a clean, dressy silhouette. Be sure to shine these up before your next big meeting.

Florsheim Indie Gore Boot, $100

Indie Plain Toe Gore Boot

Between the rich Chocolate leather color and contrasting paneling, these Chelsea boots kick things up a notch from the all-black Allen Edmonds pair seen above. The Florsehim Indie Gore Boot is perfect for pairing with dark slim jeans and a marled grey Henley — plus a suede bomber jacket — this fall season.

Mark Albert Classic Chelsea Boot in Dakota Brown, $225

Mark Albert Classic Chelsea Boot

There’s something different about Mark Albert’s classic Chelsea boots — be it the USA-made construction, the dashing and rugged leather or the stacked heel and Western last, these are Chelsea boots with a bit of edge. Wear ‘em with beat-up black or grey denim to your next rock concert — they can handle it.

Sebago Turner Waterproof Chelsea Boots, $145

Sebago Turner Chelsea Boot

If you want a pair of Chelsea boots that can stomp through the park to brunch and then back again — maybe through a light rain — the Turner Waterproof Chelsea Boots are just the pair you need. With no-nonsense cement construction and a versatile dark brown waterproof leather, these are a pair to wear with grey selvedge denim and a light blue chambray shirt for casual weekends aplenty this fall.

Common Projects Suede Chelsea Boots, $525

Common Projects Suede Chelsea Boots

Call us crazy, but it might not be a list of the best men’s Chelsea boots without including Common Projects on here. Although the brand is known for their ridiculously clean and tailored leather sneakers, the brand’s Chelsea boots are just as premium — built for the boardroom (well, some boardrooms) … and with street cred to match.