The 25 Best Mens Fall Shoes

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It isn’t hard to understand why guys would want to find the best mens fall shoes. 

Around here we’re fond of saying that shoes are the secret weapon of style: 

The right shoes can make even the most casual look seem elevated and sharp.

(Just think about how much a cool pair of Red Wings can do for casual outfits, like flannel shirts and blue jeans.) 

Chelsea boots splashing in puddle
Never forget the number one rule of fall: it will be wet
[image: Erik Mclean / Unslpash]

Unfortunately, the wrong shoes can have the exact opposite effect, and make an otherwise classy look less polished, less put together, and less attractive. 

And the cooler months of fall make it arguably the best season for men’s shoes and boots. 

The cold, wet weather may be annoying, but it gives you an excellent opportunity to rock the kind of hardy, masculine types of shoes that are too heavy to wear during the warmer months of summer. 

So to help you step up your shoe game this fall, below we’ve put together the ultimate guide to fall footwear, and included our top picks for the absolute best fall shoes to wear rock this year.

Look Awesome This Autumn:

The (Absolute) Best Mens Shoes for Fall

Brogues / Wingtips

Brogue shoes stepping in leaves
[image: Nathalia Nikolaenko / Shutterstock]

A classic style that every man needs in his shoe collection, brogues – also called wingtips – owe their origins to English hunting parties

Traditionally made from full-grain leather uppers, brogues are essentially a pair of dress shoes perforated with small holes, which were designed to let water drain out of the shoe while hunting through wet woodlands.   

Nowadays the broguing is more decorative than functional, since they’re more likely to be worn on city streets than Scottish bogs or English forests. 

But the combination of an outdoorsy origin and a sophisticated toe shape gives them a perfect balance between rugged and refined. 

That makes them the perfect shoe style for fall, and a versatile option for business casual office wear.  

You can opt for a sleeker version that you can wear with a suit to business meetings or special occasions, or go for more casual lug soles (or even shock-absorbing rubber soles, like on the Crossover Wingtip below), which work great with from skinny jeans to a pair of khakis.   

Sharp Selections:

Brogue / Wingtip Boots 

Wingtip Boots stepping in leaves
[image: Greyson Joralemon / Unsplash]

Once you get into a colder month like November or early December, even the best shoes might not be quite warm enough. 

(Plus, if you live in a northern climate like the one we have here in Toronto, there could even be a little bit of snow on the ground.) 

In that case a good pair of full grain leather wingtip boots are a great option, because they provide all the style of wingtip shoes, combined with the increased ankle support and warmth that comes from boots. 

And as with the shoes, you can decide whether you want a pair that hues more closely to the refined or rugged end of the spectrum. 

The Nolans below, from Beckett Simonon, are a sleek pair of dress boots that would work great in the office, while the Cody from Johnston & Murphy has a thicker lug sole that makes them better for casual wear. 

Sharp Selections:

Chukka Boots / Desert Boots

Suede Chukka Boots
[image: Josh Sorenson]

Chukkas are some of the overall best men’s casual shoes for just about any season (other than summer), and in fall they pretty much become my go-to shoes. 

Originally worn by British troops during the Western Desert campaign of WWII (hence the name “desert boots”), what I love about chukkas is the way they straddle the line between comfort and style. 

Let’s be honest: most comfortable shoes don’t look particularly sharp. 

But a classic pair of chukkas – like the Clarks desert boot listed below – can be just as comfortable as the best sneakers or high tops, but look sharper and more masculine. 

That makes them perfect for pounding the pavement come fall, when you want something that’s comfortable enough to wear all day, but rugged enough to befit the season. 

Sharp Selections:

Check out our roundup of the best chukka boots on the market for dozens of other stylish options.

Chelsea Boots

Beige Chelsea Boots
[image: Noah Smith / Unsplash]

Another great option for everyday wear in the fall, Chelseas offer both a unique look and a lot of ease when slipping them on or off thanks to their laceless design. 

For a long time Chelseas have been associated with hard-working brands like Blundstone, whose round-toed boots provide great arch support and all day comfort, but aren’t necessarily the sharpest or best looking boots on the market. 

Fortunately that’s started to change in recent years. 

Nowadays everyone from luxury brands like Todd Snyder to more affordable (but still high quality) brands like Beckett Simonon and Amberjack have begun to offer great-looking Chelseas with a toe shape that’s just as sophisticated as your favorite dress shoes. 

(In fact, the editorial team over at Luxe Digital called the Amberjacks “the perfect mix between style and comfort,” so you won’t have to sacrifice any support in order to look sharp.)

This new wave of Chelseas is perfect for pairing with everything from slim jeans to a casual suit, making them a great option for the office or a fall date night. 

Sharp Selections: 

Double Monk Strap Shoes

Leather double monk strap shoes
[image: Daniel Krason / Shutterstock]

There are few more dapper looking shoes than a good pair of double monk straps, and few dress shoes more appropriate for fall. 

Monk straps forego laces in favor of a leather buckle, and as you can probably guess from the name, double monks have two small buckles on either side of a large piece of leather that wraps around the top of the shoe. 

That extra bit of leather lends double monks an air of muscularity that makes them perfect for fall, while a sophisticated toe shape elevates them over even the best casual shoes. 

But the best part about double monks is how easily they can be dressed up or down. They work great with a suit for fall weddings or business meetings, but look just as sharp with a pair of jeans and a shawl collar sweater

Sharp Selections:

We’ve rounded up the best single and double monk strap shoes for men. Check out our list to get more monks! (The handsome shoes, not the contemplative clergymen.)

Suede Sneakers

Dark Brown Suede Sneakers
[image: Beckett Simonon]

A crisp pair of white sneakers is perfect for summer, but come fall it’ll be a little too hard to keep them clean. 

Of course, it’s still handy to have a good pair of minimalist sneakers on hand for the fall. 

But when the weather cools down, we recommend swapping out your white kicks in favor of suede shoes, which will be a lot easier to keep clean. 

Conventional wisdom would suggest going with a darker color like navy or black, which theoretically might be better for hiding dust, dirt and grime. 

But we’ve actually found that a lighter shade like tan or light gray can work just as well. 

And since they’re neutral colors, they’re actually easier to pair with your fall outfit

Sharp Selections:

Slip-On Shoes

[image: Wolf & Shepherd]

If you want the convenience offered by Chelseas but don’t need the extra ankle support provided by boots, a good pair of slip-on shoes can come in really handy. 

But “slip on” is a pretty far-ranging category that covers everything from super casual kicks, like the light weight pair of Wolf & Shepherd slip ons below, to sophisticated loafers like the Beckett Simonon penny loafers. 

Choosing the style that’s right for you will depend on your own personal style and circumstances. 

If you spend a lot of time working from home and rocking athleisure wear, then you’ll probably want something sportier and more casual. 

But if you’re looking for a pair to wear to the office (or maybe on a first date), then opt for something dressier like a penny loafer or a good pair of drivers. 

Sharp Selections:

Stylish Work Boot or Service Boots

Black Service Boots
[image: Logan Weaver / Unsplash]

Much like Chelseas, work boots, service boots and combat boots have been given a pretty big upgrade in recent years. 

While round-toe boots like Red Wing’s classic Iron Ranger are still a great option thanks to their goodyear welt and comfortable fit, most modern men may struggle to find the right place to wear them. 

So it’s a good thing that brands like Thursday Boots, Beckett and Allen Edmonds have stepped up (pun very much intended). 

Each brand offers modern service boots that evoke the rugged toughness of classic combat boots, but have sleeker toe shapes and a wider range of color options that make them perfect for fall.  

Sharp Selections:

Tennis Shoes

Brown Tennis Shoes
[image: Wolf & Shepherd]

Tennis shoes out-grew tennis courts a long time ago, and for good reason: 

They’re some of the most comfortable sneakers you can wear. 

But many of them also have a low heel and minimalist design that makes them look more sophisticated than other men’s sneakers, like basketball shoes, skate shoes or supportive New Balance runners. 

For fall we prefer the style that you might call dress sneakers, which often have some combination of leather, suede or canvas uppers.

Down low, they’ve got supportive features like memory foam or an EVA midsole, which make them great for retail workers and other people who spend long days on their feet.  

Sharp Selections:

Hybrid Shoes

Brown Hybrid Shoes

Pioneered by Cole Haan and perfected by direct-to-consumer startup brands, hybrid shoes – also called crossovers – are essentially a cross between a dress shoe and a sneaker. 

They’re great for fall because they give you all the cushioning, support and grip of a sneaker.

But they have a sharper toe shape and a wider range of material options for the upper.

From rugged leather and breathable mesh to sophisticated suede and more, they’re a more dressed up option than sneakers, but still provide plenty of comfort.

Sharp Selections:

For more handsome hybrids, check out our full round up of the best dress shoes that feel like sneakers. (Or don’t! I’m not the boss of you.)

Hybrid Boots

Winter crossovers

As you can probably tell by the image and name, hybrid boots are half sneaker, half boot, and (in my opinion) all awesome.

They combine the springy comfort of a sneaker with the high-ankle of a boot, giving you a more rugged look than sneakers – or the hybrid shoes listed above – without sacrificing any comfort.

While hybrid shoes can work well year-round, hybrid boots are best for fall and winter because the extra leather on the ankle provides added warmth.

(And looks great when paired with the rest of your fall or winter wardrobe, which in my opinion is just as important.)

Sharp Selections:

Cowboy Boots

Man wearing cowboy boots
[Image: Phinehas Adams / Unsplash]

I’ll be the first to admit that rocking cowboy boots in a northern climate like New York City, Chicago or Toronto is a great way to make people roll their eyes, and possibly accuse you of watching too much Yellowstone

But if you live anywhere in the American West, a classic pair of leather cowboy boots can be incredibly versatile.

And tha’ts especially true in the fall, when the ground gets muddy and you need footwear that’s rugged enough to traipse through damn near anything.  

Sharp Selections: 

More Advice on Men’s Boots, Shoes & Style from Irreverent Gent:

Banner image:
Vladislav Noseek / Shutterstock (Thanks Vladislav!)

About Dave Bowden

Dave Bowden

Founder, Irreverent Gent
Author, Man in Command and Stop Doubting, Start Dating
Writer, Really Wordy Author Bios

Dave Bowden is a style blogger, menswear expert and best-selling author (in Canada—but still!) whose advice on how to look good and live well has been featured in New York Magazine, The Wall Street Journal, Men's Health and more.

When not obsessing over style and self-improvement, he can usually be found spending time with his wonderful wife and two amazing sons, indulging in a hoppy craft beer, or sobbing over the woeful state of Toronto's sports teams.

Check out Dave's Style Story to find out how a chance encounter with his friend's step-dad taught him the value of looking good and living well (don't worry—it's less creepy than it sounds!), or email him at [email protected] if you want to get in touch.

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