The kind of rugged, badass boots that make you want to own a motorcycle—or at least pretend like you do.
Thursday Boot Co. Captain boot in dark olive suede
Thursday Boot Co.
There are newer, fresher Timbs out there, of course—but their iconic six-inch wheat model is still the one that matters most.
Timberland six-inch classic boot
Tommy Hilfiger’s fiery flip is pretty killer, too.
Tommy Hilfiger lace-up construction boot
Bulletproof, boardroom-ready brogues.
Massimo Dutti black tumbled leather boots
Dressy enough to wear with a suit, comfy enough to wear with sweats.
Astorflex Bootflex boot
J.Crew’s refined take on Blundstone’s iconic pull-tab boots is the ultimate weekend shoe.
J.Crew “Kenton” leather Chelsea boots
And the beefed-up Chelsea for puddly weekend strolls.
Blundstone men’s original 500 boots
Classic American work boots at a classic American price.
Thorogood 814-4200 moc toe tobacco
Docs are every bit as tough and versatile as you remember.
Dr Martens core 8-eye boots
The Bean boot, a true New England icon and still your most reliable option when shit really hits the fan weather-wise.
Men’s Bean Boots by L.L.Bean
You know what the brogue detailing on this pair does? It gives you an excuse to buy more than one pair of Chelsea boots.
Stacy Adams “Abner” Chelsea boots
The Hiker Mid channels the classic Timb style everyone loves, but the vibe leans a little more toward “rugged outdoors” than “’90s hip-hop.”
Timberland Hiker Mid boot
Your fave dress shoes—now with a little more ankle support.
Zara double buckled leather ankle boots
If you walk to work or take the train, this rugged lug sole will keep your boots looking good long after week one.
Allen Edmonds “Tate” Chelsea boots
Introduce your 501s to their new best friend.
Banana Republic “Tuck” split toe work boot
Wear these with black slim-straight jeans tucked in for a look that’s a little bit fashion pirate, a little bit military cop.
Camper lace-up boots
A heavy-duty sole, elastic gusset, and pull-tab in the back mean this pair only looks precious.
Jack Erwin “Ellis” rubber sole Chelsea boots
Black combat-ish lace-up boots are perfect for giving your Chelsea boots a well-deserved break from the spotlight. Even just for a weekend or two.
Timberland premium 6 inch boot
A higher ankle and soft suede fabrication give these boots an office-friendly polish.
Magnanni “Bareyo” Chelsea boots
One part hiking boot, one part sneaker, the GT Rally boot has a distinct throwback vibe.
Timberland GT Rally boot
Like this pair? Good news, they come in fourteen other colors.
Aldo “Vianello” Chelsea boots
Wallys come in more than just sand suede and black.
Clarks suede wallabee boots
The rich brown color and turned-up sole on this pair will give you that weathered cowboy look straight out of the box.
Grenson “Declan” suede Chelsea boots
These black cherry boots will wake your gray check trousers and selvage jeans right up.
Red Wing 6″ Chelsea boots
For the guy who needs an all-weather boot for the winter commute, these hit the rugged-meets-polished sweet spot, and at a very reasonable price.
Rhodes “Dean” boot
For the skinny-denim diehards—and everyone else who feels like a square in black dress shoes.
Mango leather Chelsea boots
It’s like the L.L. Bean boot and a pair of Dr. Martens had a baby.
Saturdays “Darren” duck boot
This Timberland-like spin will take you right through spring and summer—if you can keep ’em clean, that is.
Saks Fifth Avenue “Roma” Chelsea boots
Saks Off Fifth
Your navy blue suit could use a refresh; these boots and a cashmere turtleneck or crewneck would get the job done.
Zanzara “Hamel” leather Chelsea boots
Red Wing heritage classic moc 6″ boot
This pair feels more at home in a studio, garage, or warehouse than a cubicle.
UO “Lester” Western Chelsea boots
This is basically the Hummer of winter boots.
Sorel Caribou Wool Boot