With that in mind, we present the Fall Boot Guide, our blueprint for stepping into stormier climes with sure-footed confidence.

Below, we identify the five essential fall boot styles, with six examples of each to suit every budget. Plus: a series of quippy FAQs to help you determine when and why to break each of them out of the closet.



Guys who despise laces, streetwear converts and well-heeled men who regularly fend off the paparazzi.

A little band from Liverpool called the Beatles. They brought the zippered variant to America in the ‘60s. But it’s a style that’s been preferred by all kinds of music greats, from the Velvet Undergound to more recently, Kanye West.

Suede is in. Also make sure they fit snug around the ankle. The toe box should be narrow but not pointy.

Keep it simple. Any of our options below can be dressed up (a suit!) or down (jeans, white tee and leather jacket!), depending on the occasion.

Certainly. But you have to mind one very important thing: the length of your pants. Your hemline should stop right below the ankle. Not too high where it looks contrived. But just enough so you show off the shoe.

A boot that hits the ankle, usually with only two or three eyelets for lacing. Clarks makes the most iconic version.

Recovering beatniks and gents aiming for a comfortable, refined look that’ll fit any laid-back setting.

They readily accompany rolled chinos, as they do cuffed jeans. In a way, they’re foolproof, and can adapt to conform to any style.

Hiking boots that will never look out of place, whether you’re descending a summit or a subway staircase.

There’s nothing wrong with taking a little style inspiration from the great outdoors. But the point here is they can handle tough conditions and inclement weather. Who doesn’t want that?

Retro-inspired alpine hiking boots are having a moment. But these days, they’re lighter and less bulky, with traction-friendly soles to match the ruggedly appointed style.

These are a little more tricky to pull off. But easy solution: heavy-duty chinos and a flannel shirt.

A style of boot with blue-collar roots. Built strong enough to handle worksites of both the construction and office-park variety.

Detail-oriented nine-to-fivers, made-in-America enthusiasts and men who get a kick out of digging through army and navy surplus stores.

These are tough, but not that tough. If you’re looking for footwear that’ll protect your toes from wayward cinder blocks, these are not they.

Depends, really. These days you have brands like Red Wing — a company with a rugged workwear pedigree — crafting footwear that’s both tough and networking event-appropriate.

First and foremost: quality leather. Horween Leather — one of the oldest continuously running tanneries in the U.S. — has become the standard. Also you’re looking for handmade construction and durable soles.

Brogue is another word for wingtip. So these are wingtip boots, aka, the dressiest boot you’ll own.

Believe it or not, the brogue was born as an outdoor shoe favored by Irish countrymen. The perforation served an actual purpose: to help water drain from the shoe easily. These days, it’s just a handsome decoration.

Brogue boots come in many different styles. Keep in mind color, leather and the actual brogue detailing on the toe cap.

As you would a wingtip. We prefer to make them a special-occasion shoe, but feel free to rock ‘em everyday if your look allows it.

Nota bene: If you buy through the links in this article, InsideHook may earn a small share of the profits.

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