The 8 Most Comfortable Dress Shoes for Men of 2022

The Cole Haan Original Grand Wingtip Derby is our top pick.

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8-most-comfortable-dress-shoes-for-men-of-2022-tout

Ace Marks / Thursday Boots / Clarks

Nobody likes uncomfortable shoes. We’ve all experienced them — stiff dress shoes we pull out of the closet once or twice a year to attend a wedding, or when the big company boss is in town, then we come home with sore feet and blisters on our heels. The wrong pair of shoes can wreak havoc not only on your feet, but on your posture, throwing your back out of whack and causing soreness up and down your body.  Luckily, buying a stylish pair of dress shoes does not mean you need to compromise on comfort.

Our Travel + Leisure product testers were tasked to find the most comfortable men’s dress shoes on the market. We arrived at these results by analyzing 23 pairs of shoes in the following areas: out-the-box comfort; comfort after two hours of wear; comfort after a full day’s wear; and overall comfort, fit, quality and value. Ultimately, our top pick went to the Cole Haan Original Grand Wingtip Derby, a fantastically comfortable shoe that looks smart, as well.

Here are the best comfortable men’s shoes, according to our tests:

Best Overall

Cole Haan Original Grand Wingtip Derby

4.9
Cole Haan Original Grand Wingtip Derby

Nordstrom

Our Ratings
  • Fit
    5/5
  • Comfort
    4.6/5
  • Value
    5/5
  • Quality
    5/5

Why We Love It: It looks like a derby, but wears like a sneaker.

What to Consider: The sneaker sole may read a little casual for some workplaces.

Cole Haan has been synonymous with quality, craftsmanship, and excellent shoemaking for nearly 100 years. These Cole Haan classics are a best seller for a reason: they have a buttery smooth, yet supportive fit right out of the box, and are equally as pleasant for short strolls as they are for long walks.

Our reviewer appreciated the quality of the leather uppers and herringbone stitching, and admired the comfortable but supportive fit. The only area where this shoe lost a fraction of a point was for the comfort rating — because the rubber sneaker sole has a slight degree of support instead of just pure marshmallowy bounce back. But a little bit of support goes a long way and still secured the top spot for this pair of shoes. Our reviewer was able to wear them all day long and feel their back was supported, too. A removable cushioned insole adds even more comfort.

They’re also, simply put, a beautiful pair of shoes. The brogue detailing lends a heritage feel, and the grooved rubber sole offers a distinctively modern approach to a classic silhouette.

Price at time of publish: $160

Sizes: 7-15 | Material: Leather upper, rubber sole

Best Budget

Clarks Men's Tilden Cap Oxford Shoe

4.5
clarks-mens-tilden-cap-oxford-shoe

Amazon

Our Ratings
  • Fit
    4/5
  • Comfort
    5/5
  • Value
    4/5
  • Quality
    5/5

Why We Love It: This is a great shoe at a great price.

What to Consider: You’ll likely need to order a half-size up.

A pair of dress shoes for under $60? An absolute steal. The Tilden Cap Oxford from Clarks delivers everything you want from a dress shoe — great color, quality stitching, a sturdy yet comfortable sole — and they're extremely soft right out of the box. These are a great choice for city commuters and anyone getting dressed for a formal event.

Our reviewer especially loved their versatility, pairing these shoes with a variety of dress pants for the office as well as his favorite chinos and blue jeans for off-duty use. Our tester did find the fit a bit snug, so it might be best to order half a size up. Overall, however, this is a great shoe offered at fantastic value for the price.

Price at time of publish: $90 for Size 10

Sizes: 8-13 | Material: Leather

Best Boots

Thursday Boot Co. Cavalier Chelsea Boot

4.9
thursday-boot-co-cavalier-chelsea-boot

Thursday Boot Co

Our Ratings
  • Fit
    5/5
  • Comfort
    5/5
  • Value
    5/5
  • Quality
    5/5

Why We Love It: It has a versatile silhouette for formal and casual occasions alike.

What to Consider: A cork midsole means it takes a bit of time to break these shoes in.

Be stylish without being stuffy. The Cavalier has a classic Chelsea boot silhouette from Thursday Boot Co., with sleek lines, balanced proportions, and an elasticized heel band so they slip on and off with ease. They’re crafted with a cork midsole that forms to your foot over time, and the soft, hand-finished leather upper will also burnish and mold to your foot shape as well. They’re comfortable out of the box, but will grow even more comfortable after a few weeks of wear.

Our tester loved the comfort of the elastic side bands, noting that his large feet are typically tricky to squeeze into a Chelsea boot. That wasn’t the case here but he still suggested ordering a half size up from what you typically wear. Conveniently, these shoes offer a wide range of sizes, running from 6 to 16.

Price at time of publish: $190

Sizes: 6-16 | Material: Leather

Best Oxfords

Magnanni Corey Oxford Shoe

4.3
magnanni-corey-oxford-shoe

Magnanni

Our Ratings
  • Fit
    4/5
  • Comfort
    4/5
  • Value
    4/5
  • Quality
    5/5

Why We Love It: This is a quintessential, classic men’s shoe, executed to perfection.

What to Consider: The price is a bit steep.

Is there any men’s shoe more classic or versatile than an Oxford? This luxe pair from Magnanni is just about as good as heritage shoemaking gets, too. Made in Spain, hand-painted for a burnished finish, and crafted with a historic “Bologna construction” technique, this is a very light and flexible shoe.

This pair is about as comfortable as Oxfords get — not quite as plush as a loafer or sneaker, but fantastic nonetheless for the style. Our reviewer praised them as “expensive-looking” and appearing “refined”, so while the price might be higher than some Oxfords, you can rest assured that it’s money well spent. The brand also offers complimentary shipping and returns, so it’s a low-risk purchase if they don’t end up being the perfect pair for you.

Price at time of publish: $475

Sizes: 7-15 | Material: Leather

Best Loafers

Magnanni Ramiro II Apron Toe Penny Loafer

4.5
magnanni-ramiro-ii-apron-toe-penny-loafer

Magnanni

Our Ratings
  • Fit
    4/5
  • Comfort
    5/5
  • Value
    4/5
  • Quality
    5/5

Why We Love It: We love the expensive-looking, hand-painted finish.

What to Consider: These shoes are on the expensive side.

Comfort is of the utmost importance when it comes to loafers, which are often worn without socks. This pair from Magnanni scored highly when it came to out-of-the-box comfort. They’re crafted from high-quality calfskin leather and handmade in Spain, resulting in a luxe, buttery-soft feel. We love that the Ramiro II is a classic, versatile penny loafer with a modern shape. Rubber soles provide an additional level of cushion, flexibility, and comfort, and are constructed in such a way that pebbles and rocks don’t easily get stuck.

This pair got high marks from our tester for the softness and comfort of the leather uppers, noting that there was “no break-in needed with these,” as he went through a full day of events, and his feet felt great. For a penny loafer that has a broken-in feel from day one, this is a solid option.

Price at time of publish: $360

Sizes: 7-14 | Material: Leather

Most Comfortable

Mephisto Edlef Slip On

4.8
mephisto-edlef-slip-on

Nordstrom

Our Ratings
  • Fit
    5/5
  • Comfort
    5/5
  • Value
    4/5
  • Quality
    5/5

Why We Love It: We appreciate the rubber outsole with a shock-absorbent heel.

What to Consider: They have a very casual, relaxed look that may not work well for the office.

If ever there was a shoe designed for comfort, it would be the Edlef from Mephisto. The brand, founded in Sarrebourg, France in 1965 – and still headquartered there – has made its mission to produce comfortable, elegant shoes for men.

Straight out of the box, they have that soft, supple, worn-these-forever feeling. Our reviewer gave especially high marks for the quality of the leather, and noted that the toe area is not restrictive, making this a great option for guys who want a little more space in the front of the shoe. When worn with socks, our tester didn’t feel any hot spots or blisters forming, and felt more than comfortable spending hours on his feet wearing them. It’s worth noting that customers often hail Mephisto for producing particularly well-crafted shoes, often lasting for years and years.

Price at time of publish: $319

Sizes: 7-13 | Material: Leather

Best Plain Toe

Ecco City Tray Plain Toe Derby

4.3
ecco-city-tray-plain-toe-derby

Nordstrom

Our Ratings
  • Fit
    5/5
  • Comfort
    4/5
  • Value
    4/5
  • Quality
    4/5

Why We Love It: It’s a highly functional, wear-anywhere shoe.

What to Consider: The heel might feel a little formal for some men.

A plain-toe derby is one of the most versatile shoes a man can buy. Dress it up, dress it down, wear it to work, wear it to a wedding — this shoe can go everywhere. We especially loved that this City Tray derby is built with Fluidform Direct Comfort Technology, a type of comfortable-yet-supportive sole that’s lightweight and plush while still feeling anatomically supportive. It has the look of a dress shoe but the feel of something much more easygoing.

While our tester didn’t find this shoe exactly form-fitting out of the box, it didn’t feel overly stiff. There were no hot spots or blisters after several hours of wear, but he did feel that these are more geared toward an occasional special event, noting that guys who wear dress shoes every day might gravitate toward something a little more casual like a penny loafer. But all in all, these are a solid and reliable option in a highly flexible style.

Price at time of publish: $180

Sizes: 5-13 | Material: Leather

Best Fit Out of the Box

Ace Marks Cap Toe Griffin Oxford

4.5
ace-marks-cap-toe-griffin-oxford

Ace Marks

Our Ratings
  • Fit
    5/5
  • Comfort
    4/5
  • Value
    4/5
  • Quality
    5/5

Why We Love It: These shoes offer a perfect fit right away, with no need to spend weeks breaking them in.

What to Consider: They're a little pricey.

Have the Cinderella moment you deserve with the Griffin Oxford from Ace Marks. Our reviewer noted that while the leather seemed a little stiff at first, it felt perfectly broken in after just a few hours of wear. These shoes have a fit and feel that quickly become like something you’ve worn for years.

These stunning Italian dress shoes are handmade from 100% premium calfskin leather, with a classic cap toe that makes them appropriate for any office setting – yet casual enough for everyday wear. And while some shoppers might balk at the price tag of over $300 a pair, the Ace Marks’ direct-to-consumer model cuts out the middleman, so these shoes have the quality and comfort of a much more expensive pair. In short: they deliver excellent quality and comfort for the price.

Price at time of publish: $324

Sizes: 5.5-15 | Material: Leather

Our Testing Process

The T+L team tested nearly two dozen pairs of men’s dress shoes, wearing them at least three times, and testing for out-of-the-box wear, two-hour wear, and all-day wear. We took note of attributes like whether the shoes were rigid or soft out of the box, if they rubbed or chafed anywhere, and whether the fit was true to size. We judged shoes on breathability, and whether our testers found them comfortable enough for all-day wear. We wore them around the house, in cars, on city streets, to work meetings, and weddings to see how they would perform.

In the end, shoes were ranked using a points system based on comfort, fit, quality, and value. Extra points were assigned for additional features such as waterproofing, memory foaming, arch supports, and overall design. In the end, the highest-ranking pairs were selected for this roundup.

Other Men’s Shoes We Liked

Two other pairs of comfortable men’s shoes we tested didn’t quite make our list, but had noteworthy features that are still worth mentioning.

Dr. Scholl’s Sync Oxford: The name “Dr. Scholl’s” is synonymous with comfort. While this pair isn’t made from leather, it certainly has the look and feel of it. They’re so smooth, in fact, they almost feel as comfortable as your favorite sneakers or slippers. That said, their appearance is a bit too casual when compared to the other shoes on our list.

Stacy Adams Dickinson Cap Toe Oxford: Stacy Adams has been producing comfortable men’s dress shoes for over 100 years, and this Cap Toe Oxford is a perfect summation of the brand: timeless, stylish, and above all, comfortable. However, our testers reported a bit of chafing on the heel and less breathability than the other shoes on our list.

Tips for Buying Men’s Shoes

Prioritize comfort and support

Nothing will ruin a wedding or a day at the office faster than a pair of shoes that don’t fit properly, or aren’t comfortable. There are so many options out there these days that you don’t need to compromise when it comes to blending comfort and style.

Choose a versatile style and color

Dress shoes, especially when you’re looking to invest, are not the place to try something funky. Choose a color and style you know you’ll wear for multiple occasions so you can get your money’s worth — doing so will also help make sure they break in nicely over time.

Consider the intended activity

Are you going to be dancing up a storm? Go for something with a softer sole. Will there be lots of pictures, or perhaps you want to impress the boss? Opt for something a little more conservative. There’s a shoe out there for every occasion. When in doubt, ask a salesperson at your local retailer for their input.

Frequently Asked Questions
  • How should dress shoes fit?

    They should be snug enough so your heel doesn’t come up when you walk in them, but they should also be roomy enough so your toes have space to wiggle freely. Anything that feels constricting is too small; anything that slides around is too large. Just keep in mind that certain materials such as leather will also stretch out just a little over time, so a snug (but not tight) fit at the beginning is ideal.

  • How do you break in dress shoes?

    There’s no shortcut or magic potion for breaking in a pair of dress shoes. The best method is simply to wear them. If you want to make sure they’re broken in before an event like a formal wedding, we suggest wearing them around the house for a day or so until they start to feel more comfortable.

  • How should I clean dress shoes?

    Make sure to let them completely air dry before returning them to your closet, especially if you’ve been wearing them for many hours or have been sweating in them.  For exterior scuffs on leather shoes, buff them out with a bit of leather polish and a soft, clean cloth. If there’s dirt in the sole, use a damp cloth, well wrung-out, to flick off any dirty bits before returning the shoes to your closet.

Why Trust Travel + Leisure

For this story, commerce writer Todd Plummer combed through market research, in-house testing insights, and referenced product descriptions to create a comprehensive roundup of the best comfortable men’s dress shoes available today. He has tried many of the above brands himself, including Mephisto, Cole Haan, Ace Marks and more.

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