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8 Comfortable Dress Shoes for Men (Plus What to Look for in Design, Shape, Style and Fit)


Men's collection of dress shoes

The traditional men’s dress shoe doesn’t appear to have changed much over the centuries. If you’ve been avoiding buying a good pair because you’re worried about comfort, you’re in luck. While dress shoes were once made exclusively of the firm, inflexible leather, there are now plenty of stylish and comfortable dress shoes for men available.

Features to Look for When Shopping

There are a lot of choices available when it comes to men’s dress shoes, and some of them value style over comfort. That’s why it’s important to know what features make for comfortable men’s dress shoes. Here are some of the main things to look for:

Affordable prices.

Most shoes that are designed for comfort do not have a price tag as high as those built for style. This comes down to the fact they’re not made of high-end leather and generally do not come from luxury brands like Hermes or Ferragamo. There are plenty of quality brands that make comfortable men’s shoes, but they’re not going to cost $400 or $500.

Non-leather soles.

Traditionally, men’s dress shoes have leather soles, but they don’t provide much cushioning or shock absorption. While you certainly don’t want the soles of your dress shoes to have the same look as your gym shoes, there is a happy medium between that and hard leather. Look for dress shoes with a sole made of rubber or polyurethane. These lightweight materials provide both support and comfort.

Soft insoles.

The insole is the part of the shoe that sits against the bottom of your foot, and a good insole goes a long way to preventing foot pain. Look for something soft and that contours to your foot. Some have removable insoles so you can add a custom insole or orthotic if you prefer.

Leather uppers.

Closeup of brown leather dress shoes.

Leather uppers aren’t completely necessary, but they do go a long way to making sure your comfortable dress shoes still look like dress shoes and not dressed-up sneakers. Non-leather shoes tend to look a bit too casual. If possible, go for something that also has a leather-lined footbed to elevate the look a bit more.

Traditional silhouettes.

We mentioned that men’s dress shoes haven’t changed much over the years, and as such, there’s a certain expectation as to what they should look like. Stick with something that looks as traditional as possible or, again, you risk looking too casual.

Stick with neutrals.

Black and brown are the best options when it comes to dress shoes. They’re traditional for a reason, they go with just about anything. Avoid bright colors because they’ll only make you look like you’re wearing sneakers, which you’re trying to avoid.

Groom's dress shoes with watch, boutonniere and tie on both sides.

Best Comfortable Dress Shoes

Here are 8 of the best comfortable dress shoes out there, as well as a little bit about what makes them each a great choice.

1. La Milano Men’s Double Monk Strap Slip-on Loafer

La Milano Men's Double Monk Strap Slip On Loafer Leather Oxford Plain Toe Classic Casual Comfortable Dress Shoes for Men
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These shoes from La Milano have many of the features you should look for when trying to find a comfortable men’s dress shoe. They have a durable, synthetic sole, and genuine leather upper to maintain a traditional look. The plain toe design and double monk strap are trendy, but you can also adjust the straps to give your feet more wiggle room if needed.

La Milano specifically sets out to make comfortable dress shoes for men. The plain toe isn’t too narrow and, best of all, they have a memory foam insole that adjusts to your foot and provides all-day comfort. These shoes are exceedingly affordable and come in seven different colors, some with a perforated pattern across the top of the foot to allow for better airflow.

2. CLARKS Un Tailor Tie

Clarks Men's Un Tailor Tie Black Leather 7 Medium
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This simple, classic silhouette makes the CLARKS Un Tailor Tie an excellent choice. It’s simple, timeless, and yes, comfortable. The design features large, clean panels of full-grain leather that gives it a smooth look. The tongue and collar are lined with leather, too, so they’re comfortable against your foot.

The rubber sole provides traction and shock absorption, and the insole features a molded Ortholite insole over EVA foam. Add to that the rubber midsole and you have an extremely comfortable and supportive shoe.

3. Florsheim Midtown Plain Toe Oxford

Florsheim Midtown Plain Toe Oxford Cognac Smooth 7
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Another pair of great looking comfortable dress shoes for men is the Florsheim Midtown Plain Toe Oxford. It doesn’t get more classic than the Oxford style, and the full-grain leather upper gives this shoe a sophisticated look.

Other things that stand out about this shoe are the flexible and supportive rubber sole and the breathable lining. The lining is made of Suedetec, a moisture-wicking material that helps keep your feet cool and resembles soft suede.

The insole of this shoe might be the best thing about it. It’s fully-cushioned with a stability heel and shock-absorbing foam, but you can remove it if you want to replace it with a custom orthotic.

This shoe has a traditional lace-up closure and a plain toe. It’s available in black and cognac, the perfect look for any formal affair.

4. Johnston & Murphy Branning Cap Toe Shoe

Johnston & Murphy Men's XC4 Branning Cap Toe Shoe Tan Waterproof Calfskin 7 M/W US
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This stylish cap toe shoe from Johnston & Murphy features a full-grain calfskin upper and features a molded footbed and midsole for outstanding support. They’re available in tan and black and come in extra-wide sizes.

The thing that stands out about these shoes the most is that they look like a traditional pair of dress shoes. A thinner, dressier profile goes a long way to creating a sophisticated look, while reducing the weight and increasing flexibility. That’s not all – these shoes also have a seam-sealed construction which makes them completely waterproof.

5. Rockport Men’s Margin Oxford

Rockport Men's Margin Oxford,Espresso Nubuck,6 W US
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When it comes to comfortable dress shoes for men, Rockport is one of the leading brands, and this classic Oxford design is a perfect example of why. They feature a 100-percent leather upper with a synthetic sole for shock absorption and grip. The plain-toe design prevents pinched toes, and the padded collar and tongue bring additional comfort.

An EVA footbed provides a personalized fit and the PU outsole provides adequate shock absorption to reduce foot fatigue. This shoe was designed to flex, giving your foot the support it needs and the comfort you want. Plus, we love the microbial lining. You can wear this shoe all day without having to worry about foot odor.

6. Mephisto Men’s Marlon Lace-Up Oxford

Mephisto Men's Marlon, Black Pebble Grain, 6 M US
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The Marlon Lace-Up Oxford from Mephisto is a bit of an unassuming shoe, but when you take a closer look, you realize just how much it has to offer. The simple silhouette isn’t overly dressy, but it’s appropriate for most formal or semi-formal occasions. For example, it might not be the best choice for a groom at a wedding, but it’s the perfect shoe for wedding guests.

This shoe has a higher price tag than most comfortable dress shoes, but that’s primarily because of the quality of the materials. It features a leather-lined insole, milled leather, and a natural latex rubber sole with Goodyear welting for long-lasting durability.

As for comfort, the most notable feature is the air-injected midsole, which provides amazing shock absorption for all-day comfort. The pebble-grain finish is available in chestnut brown and black.

7. ECCO Men’s Seattle Tie Oxford

ECCO Men's Seattle Tie Oxford, Black, 39 EU/5-5.5 M US
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This style from ECCO has a more casual look, but it’s still a great option for a dress shoe for most formal occasions and an ideal shoe for the office. It features a 100-percent leather upper and a durable supportive synthetic sole for cushioning and shock absorption.

A textile lining lets your foot breathe and absorbs moisture to keep you cool and comfortable all day long. It comes with a leather insole that features a leather-covered inlay and ECCO’s comfort fiber system, but you can remove and replace it with your orthotic if you prefer.

8. Rockport Men’s Total Motion Sports Dress Plain Toe

Rockport Men's Total Motion Sport Dress Oxford, Black Leather, 6.5 W US
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Another great option from Rockport is the Total Motion Sports Dress shoe. This is one of the more casual options we chose, and it’s the perfect blend between a dressy leather shoe and a casual sneaker.

This shoe has a padded insole with a supportive TPU plate that provides both comfort and support, and it won’t set off any metal detectors at the airport. The round plain toe won’t pinch your toes, and the side goring and lace-up closure let you adjust the fit for comfort.

The foam footbed is soft and cushions your foot, but you can remove it if needed and use a customized orthotic for maximum comfort. There are multiple color options to choose from, including neutrals like black and brown. If you feel like adding an appropriate splash of color, go for the blue nubuck style.

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