9 Best Men’s Dress Shoes that are Super Comfortable & Dapper

Daniel Bishop
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It is important to feel comfortable in your dress shoes and to look stylish. Here are the top 9 most comfortable and stylish men’s dress shoes, with some of them being the best dress shoes.

NameCategoryProduct
La Milano Mens Double Monk Strap Slip-on Loafer Oxford Formal Business Casual Dress ShoesBest OverallLa Milano Mens Double Monk Strap Slip-on Loafer Oxford Formal Business Casual Dress Shoes
Clarks Men's Tilden Cap Oxford ShoeBudget PickClarks Men's Tilden Cap Oxford Shoe
Allen Edmonds Men's Park AvenueUpgrade PickAllen Edmonds Men's Park Avenue

1. La Milano Mens Double Monk Strap Slip-on Loafer Oxford Formal Business Casual Dress Shoes

Our rating: 9 / 10

La Milano Mens Double Monk Strap Slip-on Loafer Oxford Formal Business Casual Dress Shoes

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Pros:

  • Beautifully crafted
  • Slip-on styling with double monk strap
  • Formal enough for business and casual enough for every day
  • Available in two colors
  • Made from high quality and durable leather
  • A well-cushioned leather footbed
  • Smooth lining

This shoe from La Milano looks dapper, but it feels as soft as a pillow. That’s because of the leather upper. It’s also double monk strapped for extra support with a 3/4 inch crushed cord. The shoes are available in two colors, black and brown.

Whether you are dressing up for a party or going on a business trip you can wear these shoes with confidence. An excellent choice for any occasion.

2. Clarks Men's Tilden Cap Oxford Shoe

Our rating: 8 / 10

Clarks Men's Tilden Cap Oxford Shoe

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Pros:

  • It is a stylish oxford shoe
  • It is made of leather ensuring maximum durability
  • It ensures ease and comfort while walking
  • It’s made in an advanced shoe production facility
  • The design of the shoe is minimalistic and simple
  • The steel toe is rust resistant unlike other shoes
  • It comes in 4 different colors black, brown, grey, and navy
  • It comes in different sizes ranging from 6.5 to 12
  • It can be worn on special occasions as well as on a regular day
  • It has excellent traction

Our top pick is the Clarks Men’s Tilden Cap Oxford Shoe, which is a great looking and affordable dress shoe.

The proportions of the shoe are well thought out and they look aesthetically pleasing. These shoes aren’t too high or complicated because they are made with minimalist design.

You can wear them to the office or on a date. There are 4 different colors, which means you can wear this shoe with a different color dress shirt.

3. Cole Haan Men's Pinch Tassel Loafer

Our rating: 8 / 10

Cole Haan Men's Pinch Tassel Loafer

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Pros:

  • This is a very stylish shoe that you can wear with nearly any outfit
  • The quality leather is very soft and comfortable
  • The tread on the bottom will help you not to slip even on wet surfaces (if you’re wearing the correct size)
  • This shoe is going to look good, even if you wear it for a long time

The size is not very accurate. If you are normally a 6.5, and you order a 6.5, you’re going to have a problem.

The Cole Haan Pinch Tassel Loafer combines excellent style and comfort into a great shoe. It has a rubber sole to ensure that you won’t slip on floors, though you might want to make sure you wear socks to prevent blisters. The shoe also has a pinching tassel detail on the back, which is a unique and creative addition.

The Cole Haan Pinch Tassel Loafer has a leather upper and is available in sizes 6.0, 6.5, 7.0, 8.0, 8.5 and 9.0. It is our pick for the best dress shoes for men.

4. Stacy Adams Men's Gala Cap-Toe Tuxedo Lace-Up Oxford Shoe

Our rating: 8 / 10

Stacy Adams Men's Gala Cap-Toe Tuxedo Lace-Up Oxford Shoe

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Pros:

  • Excellent quality for the price
  • Classic shoe design
  • Goes well with a variety of clothing

Cons:

  • Company has poor quality control
  • Relatively loud compared to other dress shoes

The Stacy Adams Men’s Gala Cap-Toe Tuxedo Lace-Up Oxford Shoe is a beautiful dress shoe that will impress at any formal occasion. The design is very classic and goes well with everything from a tuxedo to a pair of khakis and a button-down shirt.

Made in Italy, they feature an elegant Burnished Brown color with dark brown burnish marks that give a nice contrast to the shoe. The upper portion of the shoe is made of good quality leather and is soft to the touch. The sole is made of rubber and feels very sturdy and durable.

Though the shoe looks very classic and conservative, don’t be fooled. These are strong shoes that can handle anything from walking on hardwood floors to pounding on the pavement. They are very comfortable and put up with extended use almost without breaking a sweat.

5. Allen Edmonds Men's Park Avenue

Our rating: 8 / 10

Allen Edmonds Men's Park Avenue

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Pros:

  • Available in a wide range of styles and variations
  • Premium leather upper
  • Extremely durable
  • Perfect for professionals and business wear
  • Tailor made and therefore you get a perfect fit
  • US manufactured

Basically all of Allen Edmonds product lines are just amazing and they are all made in America. They are quite expensive though, but these highly durable dress shoes will not only last you a long time but will also give you a good amount of style.

If you are looking for a unique and nice looking dress shoe then Allen Edmonds’ Park Avenue Oxford will probably be the best choice for you. It is made with premium full grain leather upper which means that it can last you for years even with the most rigorous of use. It has a lace-up front design and leather sole so you do not need to worry about the quality of the shoe.

6. Lacoste Men's Concours 118 1 Driving Style Loafer

Our rating: 8 / 10

Lacoste Men's Concours 118 1 Driving Style Loafer

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Pros:

  • Have a reptile upper
  • Sleek and classy look
  • Very durable and comfortable
  • Good for people who do not wear brogues that often
  • You can wear them on any occasion
  • Lacoste has exceptional customer service history

Being comfortable is something that you expect out of any shoe that you buy, and this applies to men’s dress shoes as well. This shoe will provide you with comfort that is considered the best in its class, which makes it one of the best dress shoes for office by many users.

This shoe is made from leather, and it comes in two color choices – black and brown. You can wear this shoe with just about any kind of bottom attire, but we feel that it works well with slacks.

And as the name suggests, this is a driving shoe. Meaning that you can drive in these without any discomfort and without your feet sticking to the pedals.

7. Calvin Klein Men's Atlee Ballistic Nylon Oxford

Our rating: 8 / 10

Calvin Klein Men's Atlee Ballistic Nylon Oxford

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Pros:

  • Available in four different colors
  • Good looking lace up design
  • Comfortable fit
  • Award winning design
  • High quality leather that ages well
  • Spacious toe box
  • Easy to put on and take off
  • Long lasting
  • Maintenance free
  • Reasonably priced

The Calvin Klein Men’s Atlee has a simple and clean design. The shoe has a flexible, lightweight sole that is ideal for walking outdoors and indoors. The lining is made with breathable material for added comfort.

The height of the shoe makes it suitable for indoor and outdoor use. This is a good choice for professionals who spend much of their time on their feet. It is available in four different colors – stone, tan, black, and brown sugar. The one complaint about this shoe was that it runs narrow. Just be sure to keep this in mind if you have a thin foot.

Clearly, this is one dress shoe that you are going to want to try on yourself before buying. The size differs depending on the model, but generally ranges from 9 to 13. Avoid ordering online without trying the shoe on first, just to be sure.

8. Allen Edmonds Men's Strandmok Oxford Shoe

Our rating: 6 / 10

Allen Edmonds Men's Strandmok Oxford Shoe

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Pros:

  • These are fantastic value for money
  • They are great for people who work long hours on their feet
  • The Allen Edmonds Men's Strandmok Oxford is stunningly unique
  • Allen Edmonds makes a wide variety of dressy shoes

Cons:

  • Not ideal for people who require the whole shoe as a whole or someone who wants maximum comfort
  • The Crepe Sole may not provide stability for people with wide feet

The Allen Edmonds Men’s Strandmok Oxford Shoe is one of the best dress shoe for any man.

Designed with the classic Oxford style. The Allen Edmonds Men’s Strandmok Oxford Shoe is made of soft, high-grade leather.

The leather is carefully selected in order to provide the wearer with the highest quality shoes.

Frequently Asked Questions (FAQ)

What is the most comfortable brand of men's dress shoes?

It’s always a good idea to get your shoes custom-made by the best brands but the best, most comfortable dress shoes by the best brands tend to run a bit more expensive. So my best advice for men is to look for a brand and style of dress shoe that fits well, is well-constructed, and fairly priced. A good pair of comfortable dress shoes can make all the difference on a long day of standing and walking.

What are the best quality mens dress shoes?

Quality is the hallmark of durability and comfort. While some expensive shoes fall short on durability or comfort, others come with great craftsmanship and last for years. From this category of product, you might not be looking for something that looks like a sneaker or sports shoe, but there are a few really cool options.

The key here is to pick something that’s not flashy or super trendy. For the most part, the shoes should be made of full grain leather, or at least a durable synthetic material. Avoid shoes made of flashy synthetic leather or plastic. Some quality dress shoes are obviously obvious, but you might be surprised at how often a shoe that doesn’t look particularly high quality is actually quite good!

The following nine options are what we consider the best brands of mens dress shoes that are comfortable and durable, without sacrificing style or looks.

Why are men's dress shoes uncomfortable?

Most men's dress shoes are made from pointy-toed, narrow, stiff leather that doesn't come in the widths that many men require. You could certainly require a wide shoe, however, many men don't have the ideal foot shape and require a shoe with different proportions. Do not fear! High quality, comfortable dress shoes are available for men with appropriate shoe widths as well as those with wider feet.

There are a lot of reasons why men's dress shoes are uncomfortable, but the two biggest reasons are that 1.) most dress shoes are made from narrow leather that laces up to the top of the foot, and 2.) most dress shoes are made from unsupportive materials that fail to properly conform to the shape of the foot for the best possible fit.

Which brand is best for formal shoes?

Stuart Weitzman is known for its iconic designs in shoes for men. They are always on the cutting edge when it comes to style and this brand knows better than any the importance of a comfortable men’s dress shoe. Their shoes are so comfortable, you will not want to take them off!

Another great option for men’s formal shoes is Cole Haan. Known for their unsurpassed quality, Cole Haan has been making shoes for over 125 years. They have a wide selection of very comfortable dress shoes, and their Simple Loafer is an award-winning style. The company also has a line geared toward those who work in corporate environments, known as the Dress + Gear Collection. This lineup is made for the demanding world of work and is made extremely comfortable. They still look stylish, so you will not have to compromise on either style or comfort.

Conclusion

Our Recommendation

NameCategoryProduct
La Milano Mens Double Monk Strap Slip-on Loafer Oxford Formal Business Casual Dress ShoesBest OverallLa Milano Mens Double Monk Strap Slip-on Loafer Oxford Formal Business Casual Dress Shoes
Clarks Men's Tilden Cap Oxford ShoeBudget PickClarks Men's Tilden Cap Oxford Shoe
Allen Edmonds Men's Park AvenueUpgrade PickAllen Edmonds Men's Park Avenue