10 great pairs of men’s boots to elevate your autumn wardrobe

The Dean

This is a very sexy boot, as it should be since it bears such a famous name in cool men (that’s James Dean for anyone too young to know). Western boots are having a moment this season but fear not–this boot will carry you for years to come with its versatile shape and amazing build.

Insider Cozy Lace Up Boot

You can wear these boots hiking, but they’ll look just as great with nice slacks at dinner as they would on the trails. The cushy footbed and lightweight feel makes them just as comfortable in either situation.

The Jack Boot in Aberdeen

Not for the faint of heart, Taft makes boots for the daringly stylish man who has no shame in his footwear game. Slide on these Jack boots in the gorgeously Scottish “Aberdeen” print to liven up an all-dark outfit or tie together an outfit delightfully hodgepodge in its approach.

Honcho Black

We’re not scientists around here, but our own experiments in gazing respectfully tell us men look hot in motorcycle boots. Don’t believe us? Try them for yourself and see what happens.

Men's Indiana 2.0 Steel Toe Slip Resistant Work Boot

Looking for something heavy duty in a color adaptable to any outfit that will last you years of hard work? Try these steel toes from Caterpillar. They promise the best protection you can find in a work boot, with everything from impact and compression protection to electrical hazard protection and slip resistance by ASTM guidelines.

The Valparaíso

These blue boots have personality for days, and their expert craftsmanship and made-to-order fit will feel so good, you may never take them off. Pair with a slick navy or tan suit for a vintage feel that will look fresh now or 20 years in the future.

high lace up calf boots in black faux leather on chunky sole with pocket detail

These boots are the chic intersection between goth and military, and we think you’ll look amazing pairing them with anything from cargo pants tucked in at the top to last year’s skinny jeans that need a style refresh.

Oscar Boots

The mix of textures with smooth and pebble-grain leather is a subtle but classy twist, and the shape is timeless so you’re sure to keep these around for a while. Best of all? These handsome boots are on sale for $239 right now, nearly half off their usual price.

Vegan Richards - Grey Snakeskin

Snakeskin has always been cool, but never was it cooler than when Nicolas Cage, playing the mildly deranged character of Sailor Ripley in 1990 David Lynch film Wild At Heart, mutters, “This is a snakeskin jacket! And for me it’s a symbol of my individuality and my belief in personal freedom.”

Since then, bad boys who happen to be into surrealist filmmaking everywhere have coveted the adventurous print in their accessories, including those behind these incredible vegan leather boots from Straight To Hell. Put them out, strut them out, and show off your freewheeling defiance of the status quo with panache.

Laredo Brentwood

The Western vibe is sprinkled throughout this article of course, but we had to end with a pair of honest-to-goodness cowboy boots for good measure.

The Laredos look tough as nails, with the traditional swirled leather and infamous shape that let people know you mean business. Silver detailing on the snip toes and heel add a bit of flash that looks incredibly sharp without adding unwanted pretense. For under $150, you’ll have a hard time finding a brand new cowboy boot.