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12 Essential Shoes to Complete Your Fall Footwear Collection

Having these on hand will make getting dressed for any kind of weather easy.

Headshot of Esquire EditorsBy Esquire Editors
fall shoes

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So, uh, shoes, huh? Those things you used to put on your feet before hightailing it the hell out of your sad, cramped apartment to take on the outside world? You remember shoes, right? Those things you used to look forward to busting out with some semblance of regularity? Shoes! How we feeling about 'em these days?

Listen, if you're still on the fence about "shoes" as a concept, I've got some bad news: You're going to have to wear a pair again at some point. So choose wisely. In fact, you might want to start thinking about choosing now. Because I, for one, am sick and tired of seeing people's toes out and about in the open like they're not the most repulsive part of the human body (sorry, Tarantino fans), and there's no better time to get back on board with the whole footwear proposition than this very moment.

See, shoes make up an essential part of any transitional-weather wardrobe, and if you're looking to do the damn thing right, you'll want a range of styles that mirrors the range of weather you're likely to encounter this fall. (You remember weather, right?) We're talking how-is-it-not-still-summer heat, holy-shit-it's-pouring showers, and, finally, the dreaded oh-no-winter-is-definitely-coming chills.

With all that in mind, we broke down in detail the twelve types of shoes you'll need for the season ahead, from boots (gasp!) to brogues (no!) and everything in between.

Converse The Classic Sneaker

The Classic Sneaker
Now 72% Off
$24 at Zappos

One of the best damn sneakers of all time is ideally suited for literally anything you're trying to do this fall. No, seriously. Name it. 

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Really, every season is white sneaker season. Nike's smash-hit Killshots need little in the way of introduction around these parts, but suffice to say you should be rocking these bad boys well into the warmer months, too. 

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Clarks Originals The Desert Boot

The Desert Boot

The crepe-soled chukka boot that started it all hasn't lost a lick of its appeal in the time since.  

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Milwaukee Boot Co. The Rugged Boot

The Rugged Boot

The classics are classics for a reason: everyone should have a shoe like this in their fall arsenal. Relative upstart Milwaukee Boot Co. offers a value proposition that's tough to beat. 

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Dr. Martens The Tough-as-Nails Boot

The Tough-as-Nails Boot

Dr. Martens' 1460 boots are a bona fide fall classic, and for a buck fifty you can borrow some of their timeless cool. 

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Blundstone The All-Weather Boot

The All-Weather Boot

Blundstones, we've noted before, are the Swiss Army knives of shoes. They're durable enough for any activity you have in mind and comfortable enough to allow you to do 'em all without breaking out in blisters in the process. In other words, they're the kind of shoes you buy and wonder how you ever did without. 

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G.H. Bass & Co. The Loafer

The Loafer
Now 50% Off

Two-tone loafers pack a decidedly retro-glam punch, and they couldn't look more right for this moment. Why force yourself to choose between black or brown? Life's hard enough as it is. Embrace 'em both. 

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Salomon The All-Purpose Sneaker

The All-Purpose Sneaker

Salomon's trail-ready sneakers slowly but surely became a sleeper hit among budding hiking enthusiasts and diehard fashion devotees alike, and it's hardly difficult to see why. The brand makes a hell of a shoe, and in a dark, easy-to-style colorway that'll work well with everything else you already own, investing in a pair is one of the best things you can do this season.   

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Suicoke The WFH Essential

The WFH Essential
Now 25% Off

The changing nature of our work/life realities has reshaped the way we all dress, and Suicoke's waterproof moccasins—lined with shearling and finished off with a sturdy Vibram sole—are shoes you can (and should!) wear around the house. But, crucially, you won't have to swap 'em out for another pair to step, y'know, outside. *Shudders involuntarily*

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Simply put, no one shoe embodies the type of dressing that comes to mind when I think of transitional weather than the trusty brogue—and Grenson makes some of the best. 

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Paraboot The Derby

The Derby

If you're going for a simple leather shoe, don't forget the simple part. Paraboot's signature style is anchored by a sturdy sole that sucks all the stuffiness out of the silhouette, so treat 'em the same way you would any of the sneakers above.  

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R.M.Williams The Chelsea Boot

The Chelsea Boot

The suede Chelsea boot: never not a smart play, but an especially smart one when it comes to fall dressin'. 

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