8 Most Comfortable Men’s Dress Shoes for Business and Formal Affairs

Swanky formal affairs and important business meetings require that you make great first impressions. You can accomplish that goal in comfort when you don one of the men’s dress shoes featured in this article. This list of shoes features some of the most comfortable men’s dress shoes that are suitable for work and go very well with formal wear. Envision top-notch footwear that comes from manufacturers like Clarks and Bostonian, who have been making quality footwear since the 19th century. Or, picture finely crafted footwear from relative newcomers like Rockport, ECCO and Hush Puppies. Your preferences dictate whether or not you will choose brands that are more than a century old or brands that are just decades old. But rest assured, all of these finely crafted men’s dress shoes have two things in common: They are all made from leather and they are all designed to provide you with the utmost comfort.

Most Comfortable Men’s Dress Shoes for Work

1. Clarks Men’s Tilden Cap Oxford Shoe

Clarks has made footwear since 1825 and their men’s Tilden Oxford is just one example of their line of high-quality, stylish, and supportive men’s dress shoes. The full grain leather uppers are designed to last a long time and the antique look just screams high class. The heels measure one-inch in height and the shaft is about two and one-half inches from the arch of the shoe. The lace-up closures make getting into and out of these shoes a snap, as well as providing you with a secure fit. The thermoplastic rubber outsoles of these dress shoes are both flexible and durable.

They are specifically designed to give you good traction on all types of surfaces. The inside of these dress shoes are just as amazing as the outer parts. Featuring a fabric inner lining this Clarks dress shoe will wrap your feet in luxury. The inner lining also allows your feet to stay cooler and drier. These dress shoes also feature a ortholite insole which wicks away moisture, odor and fungus. This footbed will add to your comfort level so that you can walk around all day without pain. The footbed also provides you with additional arch support while acting as shock absorbers. If you are looking for a pair of classy looking, comfortable dress shoes that will work well with business suits, formal wear, and jeans, then the Clarks men’s Tilden Oxford shoes are right for you. You can purchase these shoes in black, tan or brown.

2. Hush Puppies Men’s Rainmaker Slip-On Loafer

Love the ease of slipping on a pair of loafers? If so, then you should consider purchasing the Hush Puppies men’s rainmaker slip-on loafers. These comfortable dress shoes are suitable for all types of weather. They boast waterproof leather uppers and sealed seams to guarantee that your feet will stay dry on even the wettest of days. The heel measures one-inch in height. These dress shoes feature ZeroG technology, which makes the shoe more lightweight while still giving you quality outsole materials. The outer parts of this shoe will keep your feet warm and dry, and the inner parts are pure comfort.

The leather quarter and tongue are lined with fabric vamp. Both the instep and collar are padded to help protect the area around your ankle. The ethyl-vinyl acetate removable footbed is covered with leather and contoured to help further pamper your feet. In addition, these slip-on loafers come with a gel heel pad to minimize the effects of heel strike when walking. If you are concerned about proper arch support, you will have no worries when wearing the Hush Puppies men’s rainmaker slip-on loafers. These comfortable shoes feature ABS shank support for your arch area. With the Hush Puppies rainmaker loafers, you will get around town without worrying about wet feet, and you will do so stylishly and comfortably. The rainmaker dress shoes are available in black and black leather.

3. Clarks Men’s Escalade Step Slip-On Loafer

The last dress shoe featured in this list of most comfortable men’s shoes is Clarks men’s Escalade step slip-on loafer. Loafers are always a pleasure to wear, but these slip-ons are even better due to the full grain leather uppers that ensure you will own these shoes for a long time. The manmade sole is made to be extremely flexible and durable. It is also designed to provide you with better traction and to help with absorbing shock. The lining is made with a combination of leather, fabric, and synthetic materials.

This combination of materials is just one part of Clarks efforts to insure your comfort. An insole that is made of Ortholite foam and can be removed or put in at will is the next part. Finally, these loafers are made to accommodate special orthotics. If you have foot problems and need that bit of extra room for orthotics that will help give you that extra support, you can do so easily with the Clarks men’s Escalade loafers. These shoes are perfect for business meetings, to wear all day at work, or just for a casual night out on the town. Fashion, comfort, and the ability to choose between walnut brown and black are what you get with the Clarks men’s slip-on loafers.

4. ECCO Men’s New Jersey Lace Oxfords

ECCO is a relative newcomer to the footwear industry, but that does not mean they don’t offer comfortable and high-quality men’s dress shoes. One splendid example is their New Jersey lace Oxfords. The New Jersey lace Oxfords are made of full-grain leather, have a stacked heel, detailed stitching throughout the shoe, and boast a bicycle toe. The bicycle toe style allows the shoe to have a look that makes it great for business suits, formal attire, or casual clothes. Leather makes the shoes durable, the stitching and bicycle toe make the shoes fashionable, and the lining and insole make the shoes a dream to wear.

From the padded collar of the shoe to the insole that absorbs moisture, you will be very comfortable when donning these shoes. You will not need to worry about your feet being too hot because the insole will help to keep your feet dry. The last feature that makes these shoes desirable is the polyurethane outsole. The outsole will give you two benefits. It will give you great traction so you can feel confident that you will not lose your footing on wet surfaces, and it also acts to absorb shock. Both of these benefits are necessary if you will wear these comfortable shoes for work and have to be on the go all day. The New Jersey lace Oxfords are available in black and mink.

5. Rockport Men’s Waterproof Lead The Pack Slip-On Loafer

The Rockport Men’s Waterproof Lead The Pack Slip-On Loafer merges simplicity and class with durability and comfort. These comfortable men’s dress shoes are made with leather uppers that feature hydroshield technology. This technology offers a myriad of benefits that include waterproof leather and insoles, a gusseted tongue, and sealed seams. These benefits work together to keep your feet dry in wet weather. The thermoplastic rubber outsoles and the heel cushioning of this Rockport dress shoe help with shock absorption.

Shoes made with shock absorbers reduce foot and leg fatigue. In addition to the absorbency factor, these shoes are slip-resistant and will provide you with extra traction when walking outdoors or on potentially slippery surfaces. Rockport has gone the extra mile to craft shoes that are durable and slip-resistant, but they also have thought about your level of comfort. The lining of these shoes is made with knitted fabric and the sponge footbed is made of ethyl-vinyl acetate which is designed to conform to the contours of your feet. Durable, classy, and comfortable are words that will come to mind when you put on a pair of the Rockport men’s slip on loafer. These dress shoes will pair well with a suit or your favorite pair of jeans and you will be able to wear them all day without any problems. These comfortable dress shoes are available in black.

6. Nunn Bush Nelson Wingtip Oxford

The Nunn Bush Nelson wingtip Oxfords are traditionally stylish while offering a level of comfort usually not present in men’s dress shoes. These leather shoes are meticulously detailed in the brogue style, making them a perfect addition to pair with business suits or formal wear. The five eyelet lace up fronts makes them easy to adjust to perfectly fit your foot while the medallion styled toe of the shoe gives the classic wingtip look. Their style is just one feature of these Oxfords.

You will find that your feet are also well cushioned when you put on these comfortable dress shoes. The Nelson wingtip Oxfords are crafted with a comfort gel footbed. This footbed not only makes each step you take feel like you are walking on pillows, but it also absorbs shock. The outsole of the Nelson wingtip Oxford is designed to help keep you on your feet without weighing you down. The outsole is fashioned from manmade materials that make these dress shoes very lightweight. In addition to this, the outsoles are engineered to provide you with better traction than can be found in most dress shoes. The heels are a perfect height at one-inch. These comfortable dress shoes for men can be purchased in black, cognac, or brown.

7. Clarks Unstructured Men’s Un.Kenneth Oxford

Simplistic elegance coupled with advanced engineering in footwear makes the Clarks unstructured men’s Un.Kenneth Oxford a must have. Designed for comfort and durability, the men’s Un.Kenneth Oxford boasts full-grain leather uppers, lace up fronts for easy adjustability, lining made from lambskin which helps prevent foot blisters, and a special air circulation system that will keep your feet drier. These Oxfords are designed with air vents that allow cool air to enter through the intake vents while the exhaust vents let warm air escape.

The high-quality, removable insole is made from leather that is vegetable-tanned. This insole helps in the reduction of foot friction so you will enjoy a higher level of comfort with these shoes. The outsoles are made to be extra flexible and lightweight. Crafted with ethyl-vinyl acetate, these shoes will ease foot fatigue and reduce lift load. The outsoles also act as shock absorbers to ease the impact of walking all day long while being slip-resistant as well. The Clarks Unstructured men’s Un.Kenneth Oxfords are so finely crafted that the break-in time is limited for some and non-existent for others. From the minute you put on these Oxfords your feet will feel relieved, comforted, and you will look great wearing them too. These shoes are available in black.

8. Bostonian Men’s Ipswich Lace-Up

The Bostonian men’s Ipswich Lace up dress shoes are another example of quality and comfort. The full grain leather uppers denote high quality while adding breathability to give your feet the ability to stay cool and fresh. The one and one-quarter inch heels are the perfect height for dress shoes, while the outsole is made of ethyl-vinyl acetate materials that helps with traction and reduces foot fatigue and lift load.

Flexlite foam cushioning has been added to several areas of these shoes to make them potentially one of the most comfortable pair you will own. The tongue and collar of the men’s Ipswich lace ups are padded to provide extra softness around the ankle and forefoot areas. Foam placed between the upper lining and sock lining of the shoes provide even more comfort. There is also a removable insole that lets you have more comfort when you need it and less when you do not. These shoes are lace ups so in addition to the other outstanding features, you have the ability to adjust the shoes to your liking. If you need a pair of dress shoes that are lightweight, stylish, super comfortable, and suitable to wear all day long you really need to try a pair of the Bostonian men’s Ipswich lace-up dress shoes. These shoes can be purchased in black or brown.

Some of the most comfortable footwear suitable for business, formal wear, and just to wear as work shoes can be found in this list. Dress shoes from well established brand names like Clarks, Rockport, Bostonian and Hush Puppies will give you peace of mind that these shoes are built to last. You will also know that you will be walking around in style.