Dress shoes can connote discomfort. They sound classy, sure, but also stiff, like a shoe you can't dance in—which is a shame, as many a dress shoe occasion calls for dancing. Cue the search for a comfortable dress shoe.
Just because dress shoes—whether you're opting for a loafer, an Oxford, or a derby—are formal doesn't mean they have to lack function, in terms of cradling and supporting your feet. It's all about finding the right shoe. That means it should be well-made, with durable materials that are designed to mold to your foot over the course of months and years. But it also means that it should work with you. In the search for comfort, fit is king. If you go for something that's not the right shape for your particular foot, you're not going to be happy.
comfiest wingtip shoes
Thursday Boot Company Aviator Wingtip Dress Shoes
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Comfiest Tan Derbies
Banana Republic Oxford Leather Dress Shoes
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Comfiest Chunky Lace-Ups
Dr. Martens 1461 Mono Leather Oxford Shoes
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Comfiest Monk Straps
Nordstrom Dale Cap Toe Monk Strap Shoes
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So, yeah: You can fraternize or dance or network the night away and not be holding back shoe-related tears by the time you go home, so long as you have the right shoe. And the fact is, almost any quality dress shoe can fit that bill, so long is it's the right shape for your foot. But sometimes you need something quick. Something that puts right-out-of-the-shoebox comfort front and center. We've got a mix of both sides of the equation below. So, should you have a wedding, co*cktail party, or other fancy shindig on the horizon, and want comfortable dress shoes to wear, check out 17 of the best on the market. Your feet will thank you.
Overall Comfiest Dress Shoes
Clarks Whiddon Pace Oxford Shoes
Overall Comfiest Dress Shoes
Clarks Whiddon Pace Oxford Shoes
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We know and love Clarks for its storied dessert boots—some of the comfortable shoes around. Its "oxfords"—though, they are really derbies, thanks to the open-throat construction—fit the same bill. This sporty option, for example, doesn't only feature a bicycle-toe design, but is built with a removable Ortholite footbed that wicks away moisture and absorbs impact.
| Colors | 5 |
|---|---|
| Sizes | 7-15 |
| Materials | Leather, Rubber |
Comfiest Cap-Toe Derbies
Florsheim Medfield Cap-Toe Oxford Shoes
If the exterior of this Florsheim "oxford" (again, it's really a derby), with its genuine leather upper in rich cognac doesn't get you, the interior, with a fully cushioned insole and shock-absorbing foam, should.
| Colors | Cognac, Brown, Chocolate Brown, Black |
|---|---|
| Sizes | 7-16 |
| Materials | Leather, Rubber |
Comfiest Cap-Toe Oxfords
Magnanni 'Federico' Oxford Shoes
Comfiest Cap-Toe Oxfords
Magnanni 'Federico' Oxford Shoes
For more than seven decades, Spanish brand Magnanni has crafted the finest dress shoes, finished off with hand-made details. And the looks are only matched by the comfort, provided by the extra cushioning in the insole.
| Colors | Black |
|---|---|
| Sizes | 7-15 |
| Materials | Leather, Rubber |
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Comfiest Brogues
Samuel Hubbard Tipping Point Shoes
Comfiest Brogues
Samuel Hubbard Tipping Point Shoes
Samuel Hubbard offers up wingtip derbies with custom Vibram soles for support and balance, and triple-density memory foam footbeds for the utmost comfort. Expect your feet to feel coddled with these shoes on.
| Colors | Whiskey Tan, Black |
|---|---|
| Sizes | 7-15 |
| Materials | Leather, Rubber |
Comfiest Black Penny Loafers
Tod's Penny Loafers
Comfiest Black Penny Loafers
Tod's Penny Loafers
Tod's is known for its driving shoes, called Gomminos, with pebbled soles that give those behind the wheel greater ease when pushing the pedal to the metal. This sleek penny loafer takes the same idea as the starting point, but enlarges the pebbles and adds a thick heel for great balance and comfort while walking.
| Colors | Black, Brown, Chocolate Brown |
|---|---|
| Sizes | 6.5-15.5 |
| Materials | Leather, Rubber |
comfiest wingtip shoes
Thursday Boot Company Aviator Wingtip Dress Shoes
comfiest wingtip shoes
Thursday Boot Company Aviator Wingtip Dress Shoes
If you find yourself in a situation that calls for a brogue, have no fear. This style is exceptionally stylish and comfortable, with a chic flair that's suitable for any dressy event. With a fully-lined leather interior for maximum comfort, shock-absorbing insoles, and high-quality stitching for maximum longevity, these are a pair of shoes you'll be getting wear out of for years to come.
| Colors | Cinnamon, Chocolate, Black |
|---|---|
| Sizes | 6-16 |
| Materials | Leather, Rubber |
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Comfiest Collapsible-Heel Loafers
Gucci Horsebit Loafers with Web
Comfiest Collapsible-Heel Loafers
Gucci Horsebit Loafers with Web
The Gucci Horsebit loafer is one of the most iconic shoes in history, worn by the most stylish gents around and updated regularly. A recent refresh has placed a greater value on comfort, evidenced by the fold-down heel. After all, what's more comfortable than a slipper?
| Colors | Black |
|---|---|
| Sizes | 5-17.5 |
| Materials | Leather, Rubber, Metal |
Comfiest Tan Derbies
Banana Republic Oxford Leather Dress Shoes
Banana Republic knows how to do dressy, and these leather Oxfords with a flexible rubber outsole don't stray from their vocabulary of understated elegance. Pair with a suit, and you're good to go, no matter which color you pick.
| Colors | Cognac, Espresso, Black |
|---|---|
| Sizes | 8-12 |
| Materials | Leather, Rubber |
Comfiest Chunky Lace-Ups
Dr. Martens 1461 Mono Leather Oxford Shoes
Comfiest Chunky Lace-Ups
Dr. Martens 1461 Mono Leather Oxford Shoes
Okay, hear me out—you may have heard Docs are a pain in the ass to break in, and that's kind of true, but after you do break them in, these will be the comfiest shoes you own. They basically mold themselves to your feet as you wear them in, so the leather ends up feeling soft, the rubber is walkable, and the shoe as a whole is essentially made for you. These are versatile, too, and easy to dress up for formal occasions, or down for everyday wear.
| Colors | Black, White |
|---|---|
| Sizes | 6-14 |
| Materials | Leather, Rubber |
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Comfiest Monk Straps
Nordstrom Dale Cap Toe Monk Strap Shoes
Comfiest Monk Straps
Nordstrom Dale Cap Toe Monk Strap Shoes
These are super classy, and a little unique, too, with a dual-buckle monk strap across the top. They go with everything—trousers, a suit, you name it—and are simple, yet sleek. The best part? They have a welted rubber-tread sole, which means you'll stay comfy AF all day and night.
| Colors | Black, Brown |
|---|---|
| Sizes | 7-14 |
| Materials | Leather, Rubber |
Comfiest Iconic Derbies
J.Crew Ludlow Derbys
Comfiest Iconic Derbies
J.Crew Ludlow Derbys
These best-selling shoes are crafted with comfy, durable materials like Italian leather and a cork insole that moulds to your feet. They have an easy, breezy look that pairs well with anything from denim to wool to silk, and thanks to their impeccably chic, thin laces, you can adjust the fit to your foot as needed.
| Colors | Black, Dark Brown |
|---|---|
| Sizes | 7-14 |
| Materials | Leather, Rubber |
Comfiest Derbies Under $100
Dockers Garfield Dress Cap Toe Oxfords
With a flexible rubber sole and cushioned latex footbed for maximum comfort, these Oxfords are the ultimate fusion of affordable, fashionable, and functional.
| Colors | Tan, Black |
|---|---|
| Sizes | 7-15 |
| Materials | Synthetic Textiles, Rubber |
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Comfiest Buckled Loafers
Tom Ford Martin Burnished-Leather Loafers
Comfiest Buckled Loafers
Tom Ford Martin Burnished-Leather Loafers
Smooth, soft burnished leather and an elegant gold buckle detail kick these dress shoes up a notch. Tom Ford doesn't skimp on the comfort, though with a rounded wide toe and fabric-lined interior.
| Colors | Brown, Black |
|---|---|
| Sizes | UK 6-UK 12 |
| Materials | Leather, Rubber |
Comfiest Lug-Sole Loafers
Koio Arezzo Loafers
These chunky loafers give an edgy yet sleek look to any outfit, and with a cushiony sole and plenty of shock absorbency, they pass the comfort test, too.
| Colors | Black |
|---|---|
| Sizes | 7-13 |
| Materials | Leather, Rubber |
Comfiest Brown Penny Loafers
To Boot New York Portofino Leather Penny Loafers
Comfiest Brown Penny Loafers
To Boot New York Portofino Leather Penny Loafers
With a wide almond toe and leather lining, these are every bit the classic penny loafer, with an elegant, chic air.
| Colors | Marrone |
|---|---|
| Sizes | 6-14 |
| Materials | Leather, Rubber |
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Comfiest Chunky Loafers
Saturdays NYC Idris Loafers
Comfiest Chunky Loafers
Saturdays NYC Idris Loafers
Italian leather and big ol' soles give these stompers a distinctive look that's easy to dress up or down.
| Colors | Black, Gulf Coast, Downtown Brown, Grape Wine |
|---|---|
| Sizes | 6-13 |
| Materials | Leather, Rubber |
Comfiest Designer Derbies
Prada Spazzolato Square Toe Derby Shoes
Comfiest Designer Derbies
Prada Spazzolato Square Toe Derby Shoes
Prada knows how to do dressy, without a doubt. But with these lace-up derby loafers featuring brusher leather uppers and rubber soles, they can clearly do comfortable, too.
| Colors | Nero |
|---|---|
| Sizes | 8-13 |
| Materials | Leather, Rubber |
Tips For Choosing
When it comes to choosing any pair of shoes, prioritize your comfort. I can't tell you how many times I've been in a too-narrow, pinching pair of shoes, wishing I'd tried them on at home first.
Comfort, of course, varies from person to person, but good things to look out for are whether or not the shoe you're purchasing comes in varying widths, whether it has a high heel drop and arch support, and what kind of footbed it has. The more of any of these, the merrier (and comfier) the shoe is likely to be.
Keeping in mind where and when you're most likely to wear these shoes will also help you out in the long run. Loafers, for example, are far more versatile and easy to dress up or down than, say, brogues. You can get away with wearing one of them on a casual day much more than the other.
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How to Clean Your Dress Shoes
If your dress shoes have cleaning instructions that come with them or can be found on the website, follow those first and foremost. But if you find yourself stuck with mud or dirt caked on your shoe and no clue how to fix it, you've come to the right place.
Most dress shoes are leather with rubber soles, which are actually optimal for easy care. Start off by wiping your shoes down with a dry cloth, just to see how much dirt and debris you can clear before it's time to bring out the big guns.
A small mixture of warm water and an oil-based soap or white vinegar should remove the rest of the dirt, especially if you use a scrub brush and small, circular motions to clean. Remember: don't press too hard! These are dress shoes, after all, not your beat-up pair of Air Force 1s.
Why You Can Trust Esquire
We’re not going to say something is great unless it’s actually great. Every product in Esquire’s round-ups is carefully curated by our fashion and e-commerce teams.
When it comes to dress shoes—especially ones that emphasize comfort—, you can rest assured that we’re hand-selecting styles that we’ve personally tested, tried, and loved, along with styles that the rest of our stylish colleagues here at Esquire endorse for their own wear. We’ve had to go through a lot of trial and error, and these comfortable dress shoes are the ones that are simply the best.
Every pick on this list (and our other lists!) comes from years of wearing different things, seeing what we love and what we don’t, and going from there. No two tastes are the same, and no two men are the same. Your proverbial mileage may vary. But if you’re looking for the right place to start, with advice from folks who and care (possibly too much!) about this sort of stuff, this is the place to be.
