What Are The Most Comfortable Men’s Dress Shoes?

mcmds-1There is nothing that will give you a confidence boost and make you look more stylish than classy footwear. But classy doesn’t necessarily come at the expense of comfort. And that’s why, when shopping for footwear for a dressy occasion, you need to find yourself a nice pair of the most comfortable men’s dress shoes. Every man requires a nice pair of dress shoes, for that unavoidable occasion. Your footwear can make or break you. Regardless of whether you have the greatest suit in the world… if you are wearing bad shoes, you’re not going to look as spiffy as you can.

What To Look For In The Most Comfortable Men’s Dress Shoes?

A comfortable dress shoe gives you confidence. You will know right away, whether a dress shoe is comfortable or not. The main things to consider include the style, the interior construction, the heel height and the size of the shoe. When it comes to style, a dress shoe should either be laced or slip on. The shoe pad should be thick enough to provide good arch support. The heel is the part of the shoe that will absorb most of the shocks in your daily walking. To determine the ideal heel height, you should stand in the shoes for a few minutes and pay attention to how it feels in your leg and back muscles.

Where to Buy Cheap, Quality, Comfortable Men’s Dress Shoes Online?

mcmds-2If you are looking for a nice pair of dress shoes online, then there are several online shops to purchase. You can start with Amazon, where you will find different varieties of shoes. Additionally, you can also check on eBay, Kaymu, and Nordstrom, among others. Before you order your shoes, make sure all its features and sizings are according to your wishes, in order to increase your chances of being satisfied with your shoes upon arrival.

How Should Dress Shoes For Men Fit?

mcmds-3Before fitting dress shoes, you should know your right size. You can’t expect to ever break in a pair of shoes that is simply too small. The first time you wear them, they should fit almost perfectly. If they do not fit well the first time, they will probably never fit well. You should also consider the fact that your feet swell during the day. Therefore, it would be advisable to try out shoes in the afternoon, in order to get a more realistic feel for which size suits you. Try out the fit of the shoe with the socks that you would expect to wear normally.

What Comfortable Dress Shoes For Men Are In Style?

mcmds-4The Oxford shoe is one of the timeless and most basic shoes. This shoe is very adaptable and flexible, making it easy to combine with any casual or formal wear. It is strongly liked due to its minimalist appeal. For daily wear, it is advisable to go with a brown or black leather pair. Another shoe that is currently in style is the Monk Strap. It has a simple design, with no laces. Loafers is another timeless trend. They can be combined with a pair of jeans or other casual clothing. You should also consider Dress Boots and Boat Shoes. These are also very popular with the modern stylish man of today.

What Is The Current Trend In Dress Shoes For Men?

mcmds-5The current trend in comfortable men’s dress shoe is inspired by different designs. The Chelsea Boot is one of those dress shoes that is currently trendy. The boots have low heels and rounded toes, running at ankle length. With its simplistic look, this dress shoe can add a classic touch to your jeans. The Chukka Boot is another trendy shoe, for the gentleman who loves himself some dressy shoes. Once you wear Chukka Boots, you will be positively surprised by their comfort and simplicity. If you are looking for a shoe that you can wear to dances, operas and other formal events, then the Opera Pump is your go-to shoe.

What Is a Good Brand of Men’s Dress Shoes?

mcmds-6There are two main features, when it comes to finding a good brand of comfortable men’s shoe, materials, and construction. Leather is the main material used to make dress shoes for men. There are different leather types. However, the most common ones are corrected leather and full grain leather. Full grain leather has been minimally treated. It retains the natural leather feel. Full grain leather is more expensive than corrected leather. When it comes to construction, the main consideration, is how the sole is attached to the rest of the shoe. Goodyear Welted is a good golden standard. It is some of the most durable and breathable.

How to Choose Dress Shoes For Men?

Comfortable men’s dress shoes are available in different styles. The particular color and construction all comes down to personal style. However, there are different considerations to keep in mind, when selecting a dress shoe. If you are looking for a formal shoe, then select a sleek one. Black is considered more formal than brown. Another consideration is the lacing system. Laced shoes are a class ahead of slip-ons. Additionally, closed lacing ranks above open lacing.

What to Wear With Men’s Black, Brown, Grey and White Dress Shoes?

mcmds-7Matching your clothing to your shoes is not as hard as you think. You can do it yourself, once you’ve learned some of the basics. If you are wearing a gray suit, stick with browns and blacks. If you have a khaki suit, you can match it with any other color, except black. For people who love white suits, light brown suedes and leathers will match perfectly. A white dress shoe can coordinate with any other color, except black. On the other hand, a gray dress shoe can be worn with the majority of other colors, apart from tan and dark brown. A brown dress shoe should not be worn with black suits.

How To Polish Dress Shoes For Men?

Picking the right shoe is important, but it is important to keep them in top shape. Use a little polish, just enough to cover the surface of the shoe. Excessive polish will cause problems, and will not shine the shoe. After removing excess polish from the shoe and buffing with a brush, sprinkle a little water on it. A small amount of elbow grease should also be applied after the first shine. Shine the heel and toe again since they are the most visible parts of your shoe. A second shine is an indication that you are someone who cares about his shoes.

How To Keep Dress Shoes For Men From Creasing?

Preventing the shoes from creasing is part of taking proper care of dress shoes. When putting the shoes on, it is advisable to use a shoehorn. Remove the shoes from your feet gently, using your hands to slip them off. If you are not wearing them, insert cedar shoe trees. When you are travelling, it is important to store your shoes inside dust bags, to prevent entry of moisture. Additionally, store your shoes away from heat. Shoes should dry naturally. Heat might cause leather to crease and age.

Most Comfortable Men’s Dress Shoes Reviews

1. Allen Edmonds Men’s Carlyle Oxford

A timeless classic, the Carlyle model is extremely clean and elegant. The high quality exceeds expectations and you will not be disappointed. This is one of the most comfortable men’s dress shoes money can buy currently. It is mainly associated with men who love class and style. The stitching on these shoes is done by hand. Additionally, the impeccable calfskin and the burnishing on the toe gives this dress shoe a great shine.

It comes with a design that features a tapered, elongated toe, giving it the perfect attitude, for the modern man that loves success. It is finished with a regular heel and a single leather sole, instilling you with confidence everywhere you go. The shoes are durable, stylish and reliable. For matching, consider wearing them with a blue or brown suit. It is available in a variety of styles, and can be worn for different occasions.

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2. Allen-Edmonds Men’s Fifth Avenue Walnut Calf Oxford Shoe

The Fifth Avenue Oxford Shoe is one designed for the consummate professional gentleman. The sleek silhouetted, couple with the perfing on the cap-toe gives this shoe the right sense of personality. The upper is made of lined premium calfskin leather for guaranteed longevity. A Goodyear welted construction and a single oak leather sole ensure a tailored fit. Moreover, the shoe is recraftable. Whichever office you work in, this shoe is perfect for everyone. With impeccable craftsmanship and a sophisticated cap toe, you will realize that this is an iconic shoe, with every step you make.

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3. Allen Edmonds Men’s McAllister Wing Tip

First designed in 1956 and re-introduced in 2009 by popular demand, this comfortable dress shoe dates back hundreds of years. Over the years, this shoe has become a must-have with its conventional 5-last fit. The perfing on the throat, backstay, and wing, along with the intricate toe medallion and pinking, makes these shoes durable and refined.

With its classic styling, the distinguished perforation detail, and the rich leather upper, this dress shoe will give your dress wardrobe the perfect polish. It also comes with a dust bag. They are stylish yet conservative, moisture absorbing and very comfortable. The cuts and stitching come with the right consistency.

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4. Allen Edmonds Men’s Strand Cap-Toe Oxford

If you are looking of a shoe that can put a final polish on your professional look, then the Strand Wingtip Oxford is your go to shoe. The calf leather upper and the perforation detail, gives it a distinguished air. A shankless construction removes the need for a break-in period, giving you a comfortable fit right away.

A 360-welt design and construction binds the footbed, the sole, and the upper, giving the shoe extraordinary flexibility, comfort and durability. The contoured last has been intentionally designed, to resemble men’s feet, giving you the perfect fit. The full leather lining is breathable and soft while the oak leather sole flexes with the foot naturally.

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5. Armani Jeans Men’s Dress SN Fashion Sneaker

A comfortable men’s dress shoe, the Armani Fashion Sneaker is an exceptional dress shoe that fits perfectly. It is a well-constructed shoe, with a durable sole and full grain leather upper, which makes it one of the most durable shoes today. It is a trendy shoe that can be worn to the workplace. Alternatively, you can combine it with a pair of jeans, and still look classy. You can never go wrong with Armani Jeans Men’s Dress SN Fashion Sneaker. It is avialble in black and brown, giving you a wide range of color choices to match.

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6. To Boot New York Men’s Felix Oxford Shoe

A plain-toe oxford remains one of the most versatile shoes. This one offers superior, Italian-made quality. The leather upper has been constructed with minimal lines, making it the ideal choice for slacks, denim, and even better suits. A leather lining keeps the shoe breathable and cool. On top of that, there is a textured rubber outsole that is durable, massaging and durable.

The shoe and all its accessories are made in Italy in one of the finest factories. Each part and accessory is made of the finest French and Italian leathers that is passed through more than 200 steps during its production. The quality of the shoe, together with the accessories makes this comfortable men’s dress shoe the perfect choice for your lifestyle.

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7. Bostonian Men’s Ricardo Cap-Toe Oxford

Bostonian has been producing stylish and trendy shoes, for more than 100 years. Their shoes are manufactured with top quality materials giving you the quality you desire and the options you demand. The shoes fit well and the price is more than fair, considering the quality that you will get. They feel comfortable, are constructed well, and look sharp and dressy. The interior comes with a cushioned footbed and moisture-managing lining for arch support.

The contrast looks great. The color, a reddish-brown hue, can be complemented with several outfits. If you have normal feet, you should order a half-size smaller, since the shoes run wide. This dress shoe has been finished with a protective rubber and leather sole for traction and durability. The shoe is made from premium, smooth leather, coupled with a contrasting leather panel wrapping on the midsole for a unique detail.

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8. Bruno Magli Men’s Maioco Lace-Up Dress Shoe

Most Bruno Magli footwear is manufactured using Nappa leather that is derived from goat skin. This results in a more supple and softer upper, something that is not possible with calf leather. The result is a very comfortable dress shoe. In terms of style, the shoe is simply gorgeous. The lightly tapered toe gives the shoe a slender silhouette. It’s stylish but still conservative.

The Maioco features a cap toe design coupled with a sleek six eyelet. A leather sole, a nappa leather upper, together with a flexible leather outsole, gives the shoe a stylish appearance. If you want to define your personal style, then you should consider the rich look of this oxford from Bruno Magli. This comfortable dress shoe has a semi-polished, smooth leather upper with a lace-up closure design.

A cushioned insole, a dress leather outsole, and lightly waxed laces, gives you optimum comfort when attenting your next business meeting. The Maioco is classy enough for combining with tuxedos, if you are attending a special occasion. The shoe is handmade in Italy, and comes with protective bags to be used for storage.

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9. Cole Haan Men’s Garrett Grand Wingtip Oxford

With more than 80 years in shoe design and production, and thousands of distribution points across the globe, Cole Haan is one of the premier luxury brands, when it comes to making comfortable men’s dress shoes. The shoe has impeccable craftsmanship and artisan quality in today’s world, where style is everything. A well-made and beautifully designed shoe, the Wingtip Oxford is ideal for today’s dapper gentleman.

The Cole Haan Grand Wingtip Oxford fits perfectly while giving you the comfort that you are looking for in leather dress shoes. They have good support, feel great and look great. You should be able to wear them for a long time, without needing a replacement. It bends easily, which means that you don’t require significant break-in time. The rubber sole gives you good traction, so you won’t have to worry about slipping when walking on wet floors. They are perfectly crafted classic shoes made of genuine leather. Overall, they are comfortable and dressy.

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10. Cole Haan Men’s Lenox Hill Cap Oxford

The Lenox Hill Cap Oxford features a simple detail. It is a modern shoe that a streamlined take, on the previous versions. With cap toe accents and polished leather uppers, they add a razor sharp edge to a slim and tailored suit, leather jacket or even jeans. The uppers have been made of full-grain cow leather while the shoe is fully leather lined. A full and sleek rubber cup outsole caps off this stylish shoe.

Mini stacked heel and lace-up construction adds to the overall comfort. They are flexible, versatile, and good-looking shoes. They take a minimal time for breaking in. With a brown shade, you can match these shoes with a belt and you’ll stand out. If you are looking for great shoes with non-slip rubber inserts and a sturdy heel, then look no further.

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11. Donald J Pliner Men’s Rex Slip-On

This Donald J Pliner slip-on is perfect for an evening in town or daily office wear. The shoe features a rich leather upper, combined with minimal seams for that sleek look. The interior part has leather linings, for superior breathability. The leather outsole has been fitted with rubber overlays for increased durability and steadying your step.

When you are feeling comfortable from the bottom up, then your body and mind are at ease. With that in mind, the shoe has been designed to meet high standards of perfection and quality, together with innovativeness. This luxuriously comfortable footwear has established the right balanced between fashion and creativity.

Since its introduction in 1989, the shoe has maintained a high style and innovative design. With materials such as stretchable micro fibers, the shoe brings flexibility, unprecedented comfort, and lightness. Manufactured in both Spain and Italy, this shoe is popular around the globe with men who appreciate craftsmanship, comfort and style in a neatly bundled package.

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12. ECCO Men’s Windsor Tie Oxford

Create a style of sophistication, with this Windsor Tie. This lace-up has been manufactured with rich leather uppers. It features moc toe stitching and a five-eyelet closure. A leather lining offers smooth comfort. A one component, directly injected outsole acts as a shock absorber while increasing cushioning. You will find the best in comfort and innovative elegance in the ECCO Men’s Windsor Tie Oxford.

This shoe will give you a sleek look, as well as giving your wardrobe practicality. Made with smooth leather, this shoe also comes with breathable leather linings, a lightly padded collar and a moisture absorbing sole for additional comfort. It is one of the most comfortable men’s dress shoe, for getting through your work day. It is one of the few shoes in the market today, that has leather on both sides. Despite the leather being soft and supple, it maintains its great shape for a long time. The insole is soft and well tailored and is removable. Therefore, you can replace the insoles with your own, should the need arise.

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13. ECCO Men’s Windsor Slip-On Dress Shoe

ECCO holds itself to very high standards, when it comes to comfort and durability. This Slip-on dress shoe is comfortable and classic. It features lightweight fiber system uppers for increased circulation and minimal odor. A one component, directly injected outsole acts as a shock absorber. The uppers have been made from full-grain, smooth leather, for that sophisticated appearance.

It is a great dress shoe for your workdays, which gives you style, while still feeling comfortable. You will definitely love the feel of this shoe when wearing it. They fit perfectly on your feet, giving you the freedom you need when going about your day. It comes with a roomy toe box, and is wide enough to accommodate different widths.

The shoe allows your toes to spread naturally, thereby supporting your weight and fostering a comfortable walking experience. It is comfortable straight out of the box. The ECCO Men’s Windsor Slip-On Dress Shoe is a solid shoe, incredibly comfortable and it wears well. It is dressy enough to be combined with a suit. The shoes are so light, that you would think you were wearing sneakers instead of dress shoes.

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14. Johnston & Murphy Men’s Greenwich Oxford

This stylish dress shoe features a unique wingtip styleline on the exterior, and a trampoline cushioning system internally. It can be both a formal wear and an every day office wear shoe. The shoe has a flawless profile, crafted with refined leather. This dressy lace-up comes with a classic oxford perforation detailing, an insole cushion, an added heel and a breathable lining. All of which ensure that your feet will remain comfortable all day long.

They are great looking shoes, running almost true to size. A good pair of wingtips is essential for your business wardrobe. That is why you should consider adding this classic shoe to your collection. Construction, appearance, and fit are all excellent. Additionally, the shoes are not clunky, as compared to other wingtips. You can wear these shoes when you are going for a job interview, a court session or a business meeting.

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15. Magnanni Men’s Pardo Lace-Up Dress Shoe

If you are looking for a dress shoe to spice up your professional wardrobe, then this stylish oxford is a great choice. The shoe features a shiny leather upper, done with classic stitching together with a lace-up front, to give you the perfect fit. With a grippy rubber outsole and a comfortable leather lining, this is one shoe that will always place you above the rest, in your professional career.

For more than fifty years, this company has produced excellent footwear, combining distinctive hand detailing and finishes with elegant designs. The shoe is manufactured using the finest materials and leathers, as well as solid construction for maximum comfort and flexibility with every step you take. Apart from being comfortable, the shoe is very gorgeous, together with a non-slip sole that has been incorporated in the new designs. They only require wearing them once or twice, before they are broken in. After that, the shoes are super comfortable. They are definitely stylish and combine well with the various suits you undoubtedly have in your wardrobe.

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16. Mezlan Men’s Soka Cap Toe Oxford

The Mezlan Soka is a classic shoe for the classy man. It features a cap toe, soft Italian calfskin linings and a cushioned insole made from injected foam. The shoe comes from a long line of exceptionally crafted and imagined footwear with a lace-up design. A luxurious leather sole and trademark tassel laces, provide the perfect finishing touches to this elegant shoe. These shoes will complete your outfit in such a way that, whenever you set foot out of the house, you are definitely going to get some looks.

They are well-made, great looking and classy. The leather upper is highly polished. The matter section of the upper is soft, handsome and gives optimum flexibility. Their laces have been lightly waxed and the fit is just perfect. It is a good quality shoe that is absolutely worth the price. The shoe successfully combines a textured and smooth leather upper, a memory foam comfort midsole, a leather sole and a squared cap toe.

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17. Mezlan Men’s Tyson II Oxford

This dress shoe is an updated classic oxford manufactured with high shine Italian calfskin. The inlay is made of genuine deer leather. A memory foam insole and artisan outsole, will give you the walk of your life. This handstitched oxford is smooth and sleek. The shoe also features leather linings, a dress sole and a cushioned midsole. It all comes together very well to create a super stylish shoe, that also handles shock absorption very well. The Tyson II is a comfortable men’s dress shoe that you can wear to various occasions.

They are classy enough for a professional setting, while still maintaining a dressy appeal when you are wearing them, so you can be sure to look super sharp. With its shiny finish, you simply need to wipe with a damp cloth, and you are ready to head off to your corporate meeting with full confidence. A fabric and leather lining on the inside, will make sure that your feet remain snug. Mezlan is an ideal shoe brand for the man who wants durable shoes, while remaining stylish.

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18. Red Wing Heritage Men’s Postman Oxford 101

Red Wing dates back more than 50 years ago. It is sturdy and comfortable footwear, for people who spend more than eight hours a day standing up at work. This sturdy oxford can be polished to meet your workplace requirements. It features a crepe wedge outsole and Goodyear Welt construction for comfort and durability all day long. Get the support and comfort that you need, with the Red Wing Oxford 101.

They are top quality work shoes, that kind of feel sturdy like work boots. They are handmade and top quality. The shoe continues to evolve, to meet the demands of the modern generation. The company is credited for manufacturing tough durable footwear, that can handle all sorts of challenges. These dress shoes are created with durability, comfort, quality, and craftsmanship in mind. It is a shoe that is guaranteed to serve for long. The style and functionality of these shoes, in combination with the wedge sole, helps you in moving your feet more comfortably. They are highly recommended for someone who wants work shoes, but still want to look stylish.

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19. Samuel Hubbard Mens Founder Oxford

This oxford gives you an air of authority, whether you are walking around in the street or at the office. It complements your tailored blue jeans or a good pair of dress slacks. The welting, made from genuine leather, the refined eyelets, and the waxed laces highlight the great leather uppers. The shoes do not require a break-in period and fits well straight out of the box. The shoes have been fully lined with cowhide leather.

The shoes do not have any glue between the linings and the uppers, so that they can conform to your feet and breathe naturally. They come with triple density orthotic, created with vegetable tanned leather and Poron memory foam, to give your feet the most comfortable fit of their life. The combination of Hubbard vibram soles and soft leathers, make these some of the most comfortable men’s dress shoes for long day wear. Whether you are a man on the go, or you spend long hours sitting, then these springy and light shoes are perfect for you.

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20. Vivobarefoot Men’s Lisbon Shoe

Lisbon is a beautifully crafted formal dress shoe for men. The polished, buffed leather, plus a slight rocker heel, gives you premium style and also let your feet breathe effortlessly. This is the ideal shoe for the real gentleman. With a flexible, super thin sole, the shoe is designed to suit your natural movement. It is fine-tuned to meet all your events. Unlike most dress shoes, the shoe fits perfectly. It comes with a roamy toe box, to ensure your toes stretch and move freely.

The Vivobarefoot Men’s Lisbon Shoe is one of the most comfortable dress shoes you can find on today’s market. The zero-drop helps to spread the weight on the feet evenly, which means you are unlikely to develop foot pain. The workmanship is good, and the leather is high quality. They are comfortable and fit perfectly.

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Bottom line

Shoes can be expensive at times; however, if you make smart choices, they will serve you for years on end. Additionally, the confidence they give you when you are wearing them, makes it worth the cost.

Check out my walking shoes navigation page to read about many more shoes!

Table of Contents

Author Biography

This page was authored by , who represents the Boot Bomb. Brian is backed up by an expert team, made up of experienced family and friends, all of which are knowledgeable in the ways of footwear and/or hiking. His ancestors used to own a shoe store for almost a century. He has lived and breathed footwear for as long as he can remember.

This page was last updated on .


  1. I am standing in the most comfortable shoes I ever owned, casual oxfords, tan leather laces, rubber soles. I bought them in 1996 and have worn them to scout camp, to teach in and to spend three months walking around Europe with college students. After that I was able to replace the original soles with vibram. Bass model 5917. No longer made, of course.

    • Thanks for the feedback, Don.

      We all know that feeling when our favorite shoes finally wear out and they’re no longer being made!

      Times change. And so do shoes. We should all find comfort in the fact that shoe technology has come a long way in 20 years!

  2. Thank you for posting this helpful blog about choosing the right kind of dress shoes to walk around. I will definitely keep these points in my mind the next time I’ll be buying dress shoes. This post will serve as a handy guide for dress shoes. Looking forward to read your next interesting post.

  3. Thanks Brian. Your plantar fasciitis list for walking shoes was a life-changer for me. How about a PF list for dress/business casual shoes? I walk into JohnstonMurphy stores and everything is either too flexible or too snug for my orthotic.

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