30 Essential Men’s Boots for Fall and Winter

Your boots say a lot about you. Make sure they're smart.

October 30, 2019 2:06 pm
30 Essential Men’s Boots for Fall and Winter

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They say you can’t judge a man until you’ve walked a mile in his shoes.

We say you’re fine just looking at them.

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.

Lace ‘em up.

The Chelsea Boot

So what are these?

An ankle-high slip-on boot. You know the maxim “less is more”? This is that, in footwear form.

Who are they for?

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

They look familiar. Where have I seen ‘em before?

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.

Wait, only rock stars can wear them?

Absolutely not. But make no mistake: it will give you a more youthful appearance. 

What am I looking for?

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

And about how to wear it?

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.

So wait, I can wear a suit with these?

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.

To Boot Shelby

Rhodes Chelsea

Taft Outback Boot

Frye Grady Chelsea

Common Projects Chelsea

Paul Evans Dean Chelsea

The Chukka Boot

So what are these?

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

Oh, you mean desert boots?

Not exactly. All desert boots are chukkas but not all chukkas are desert boots.

What’s the difference then?

Desert boots sport a crepe sole. No crepe sole? Then it’s just a chukka.

Who’s it for?

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

How laid-back are we talking?

Think casual Fridays. Saturday nights at the bar. Sunday mornings at brunch.

How do I style them?

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

Clarks Desert Boot

Rhodes Felix Chukka

Wolverine Hartwell Chukka

Red Wing Classic Chukka

Mr. P Lucien Suede Boots

Alden Chukka Boots

The Hiking Boot

So what are these?

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

Who’s it for?

Men who like winter, seasoned campers and off-duty outdoorsmen who can’t escape the city.

If you’re not hiking in them, what’s the point?

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?

What am I looking for?

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.

How do I style them?

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

Timberland Ripcord Mid Hiking Boots

Shoe the Bear Lawrence Hiking Boot

Vasque Clarion ’88 GTX

Reiss Harold Hiking Boots

Oakstreet Bootmakers Natural Rough-Out Danite Summit Boot

Diemme Everest Hiking Boot

The Work Boot

So what are these?

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

Who’s it for?

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

We talking steel-toe caps then?

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.

So work boots but not “work” boots?

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.

What am I looking for?

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.

What should I wear ‘em with?

They accompany casual clothing and workwear, like denim and chambrays.

L.L. Bean Kathadin Iron Works Engineer Boots

Thursday Vanguard Boot

Grant Stone Plain-Toe Boot

Allen Edmonds Higgins Mill

Wolverine 1000 Mile Plain-Toe

Todd Snyder x Alden Indy Boot in Green Suede

The Brogue

So what are these?

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

What’s with those holes, anyway?

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.

Who’s it for?

Southern dandies and men who enjoy their Scotch neat.

What am I looking for?

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

So these can be worn with a suit?

Absolutely. But unlike, say, the Chelsea boot, you needn’t mind your hemline.

How else can I style ‘em?

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.

Base London Hurst Wingtip Boot

Taft Holt Boot

Grenson Shane Boot

Frye Graham

Magnanni Macario Boot

Thom Browne Wingtip Boots

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