Most Comfortable Dress shoes for Men

If you’re looking for the top 10 most comfortable dress shoes for men standing all day long, you’re taking good care of your feet health. Studies have shown that wearing good supportive, comfortable shoes can reduce back pain, reduce leg pain and contribute to your overall good health. If you work in retail, cashier, security, mechanics, firefighting,  a teacher, a pharmacist, a doctor or a nurse, you’re on your feet all day long, and you probably suffer from some back pain and leg pain. Wearing the proper shoes will go far in helping to ease your discomfort.

An essential qualification for a pair of dress shoes is an overall sense of style and class, a classic feel that meshes well with formal attire such as special occasions as well as being suitable for professional environments. 

Here are few tips for finding the most comfortable shoes:

  • Visit the local running shoe store such as New Balance to determine the type of arch and gait. Do not forget to take your worn out shoe for evaluation to find out overpronation or underpronation.
  • Look for shoe with wide toe box
  • Breathable
  • Good cushioning and arch support
  • Use insoles for additional cushion and support
  • Look for rocker sole shoes if you feel pain in the ball of the foot
  • See the podiatrist if foot pain persists in spite of above measures

If there’s one negative to your typical, run of the mill dress shoe, it’s that the things just aren’t all that comfortable. They tend to have thinner soles than the likes of the sneakers or boots a lot of us are used to, and their material is often all about style before anything else. It doesn’t help matters any that they also tend to fit a lot differently than other shoes as well. Fortunately, if you find yourself in a position where you need the snazziest shoes available for long periods of time, there are at least a few models out there that won’t leave you with blisters and sore ankles at the end of the day. To help point you in the right direction, let’s go over the list of the most comfortable dress shoes for men!

Although there are many brands of men’s shoes on the market, all of them are not created equal. The most comfortable dress shoes for men may not be the easiest to find. Our top dress shoe picks are based on an excellent arch support, firm midsole, roomy toe box, and closed back. Many of these shoes offer removable footbed for orthotic replacement. If you are suffering from foot pain, try gel inserts and if pain persists, then see the podiatrist for the evaluation of your feet.

ECCO Helsinki Cap-Toe Oxford Dress Shoe

ECCO Men's Helsinki Cap-Toe Oxford Dress Shoe

ECCO Men's Helsinki Cap-Toe Oxford Dress ShoeEcco men dress shoes are one of the most comfortable shoes, looking good and last long time. Available in both black and brown, this midline-priced shoe is ideal if you’re seeking a contemporary, refined look. Handsome seaming graces this leather upper and moisture-wicking lining and a padded insole ensure that your foot can easily breathe. Excellent arch support, wide toe box, and a good cap toe give this shoe a classy look. Easy to wipe clean with a damp cloth your feet will appreciate this long wearing durable shoe.

This dress shoe for men offers a removable insole for orthotics insertion. The polyurethane direct injected outsole is one component that provides adequate cushioning. The built-in shock point in the heel of outsole provides additional cushioning and support.

If you are on feet a lot and have bunions, Ecco dress shoes will not cause your feet sore at the end of the day and will provide roomy toe box to accommodate bunions. Use dress shoe insoles if you need more cushioning and support. These shoes are expensive but they are one of the most comfortable dress shoes for men.

 Hush Puppies Leverage

Hush Puppies Leverage

Hush Puppies LeverageThe Hush Puppies Leverage helps you tackle the obstacles in life in style and comfort. The seam-sealed construction and waterproof leather upper help keep your feet dry all day long. The padded tongue and collar of the shoe will provide additional support as well as comfort. It includes a breathable textile lining and cushioned textile insole. The shoe comes with a slip-on design and elastic gore at each side of it for a bit of stretch. The novel “ZeroG” construction technology makes the shoe ultra lightweight which helps prevent fatigue when worn for longer periods. The durable rubber outsole and airport-friendly non-metal shank are the other salient features of the shoe.

Many clients have reviewed the pair of shoes positively on numerous online review sites. One reviewer has said that the shoes are quite comfortable and nice enough to wear with khakis and a dress shirt. It can also be dressed down with jeans as per another opinion. Most clients have found the gel pad under the heel to extremely comfortable for longer wear. All in all, the Hush Puppies Leverage is one of the most comfortable dress shoes for men on the market today.

Clarks Unstructured Un.Sheridan Slip On

Clarks Unstructured Men's Un.Sheridan Slip On

Clarks Unstructured Men's Un.Sheridan Slip OnThis middle of the line priced slip on shoe provides all of the comfort expected in a good shoe, without the lacing. Quick and easy to get in and out of when necessary your feet will appreciate the finer things in life when you’re wearing these. A unique ventilation system allows your feet a cooling refreshing breathable air that will help to reduce moisture. Premium full-grain leather upper means that these are easy to care for and wipe clean with a damp cloth. No need to break these shoes in, you will want to wear them all day long and won’t mind a bit. Special lambskin lining offers your foot the best comfort available. Lightweight ultra flex means that your feet aren’t going to be working overtime to walk around.

This entry on the list of the 4 most comfortable dress shoes for men brings us to the Clarks Unstructured Un.Sheridan. This brings another slip on into the fold, making it perfect for those of you who like to step right into your shoes and go in the mornings. There’s a bit more size range available here than with the others; this shoe can accommodate those that wear sizes 7 through 17. The materials are about the same as you would expect; all of the usual suspects are here, but there’s also the interesting addition of lamb’s skin lining to help reduce the possibility of blisters. The snazzy aesthetic is also bolstered by a vegetable staining process that’s truly unique! If you want in on these, expect to pay between $130 and $170.

 Dunham by New Balance Burlington Waterproof Oxford

Dunham by New Balance Burlington Waterproof Oxford

Dunham by New Balance Burlington Waterproof OxfordThe Dunham’s by New Balance are a pair of stability dress shoes equipped with a chic sophistication that extends to its function as well as its aesthetic appeal. These lace ups feature a classic look and feel with its full grain polished leather upper, offering a classic look that incorporates some highly modern waterproof construction to keep your feet dry. The EVA foam in the removable footbed, providing cushioning and shock protection. Approved by Medicare for Diabetic feet, they also offer stability shank to support arches and keeps your gait in the neutral position.

The rounded toe box makes the Dunham’s plentifully spacious for feet of most descriptions, giving your toes that extra wiggle room to keep the circulation flowing and giving you room to stretch. Inside the shoe we find a textile lining in addition to the plush cushioning, making the Dunham’s notable for their excellent comfort.

Not out of place at a wedding or dance, the Dunham’s have plenty of class and appeal. But they are also at home as a selection for all-day wear, making them an excellent choice for the professional work environment. Waterproofing and ABZORB cushioning even makes them suited for a bit of heavy foot work!

If you are looking a diabetic and weatherproof pair of oxford dress shoes with good arch support, Burlington is one of the most comfortable shoes for standing and walking all day.

 Dansko Walker Oxford

Dansko Walker Oxford

Dansko Walker OxfordDansko is another fine shoe manufacturer, and their Walker Oxford style can’t possibly come more recommended. While you do have to lace these up, you can put any worries that they won’t stay to rest right now. Everything is of quality construction here, through and through. Genuine leather, rubber, and slip resistant rubber are all included in the overall composition, and the comfort is notably strong.

Available in sizes 7 through 15, the Dansko Walker will run you around $130 to $140. This won’t exactly be a drop in the bucket for most budgets out there, but it’s exactly in line with what you should be expecting to pay for a shoe with some actual quality and care behind its manufacturing process. Best of all, it has a very simple aesthetic that perfectly blends the appeal of casual and dressy.

This rugged leather shoe is casual and gives you a laid back look. A rounded toe and lace up front will round out the look and works great with both jeans and dress pants. The padded lining and the excellent arch support keep you comfortable throughout your busy day. Reasonably priced you can find these online or in most retail shoe stores. The certified slip resistant outer sole ensures that you’ll be comfortable all day long.

These shoes are very easy to clean by just wiping them off with a clean damp cloth.

 Rockport Northfield Waterproof Oxford

Rockport Men's Northfield Waterproof Oxford


Rockport Men's Northfield Waterproof OxfordAre you Still looking for the most comfortable dress shoes for men standing all day? This shoe is considered one of the best selling shoes on the market today. Whether you need something for the office or something for a night out, this is the ideal shoe. A padded tongue and an ankle collar give it a unique style and a long lasting comfort all its own. Latex footbed offers comfort cushion and reduces foot pressure spots that can become very tender and painful if you’re on your feet a lot during the day. Easy to clean full grain leather helps you to keep your shoes looking great.

The Rockport Northfield is available as both an Oxford shoe and a Chukka Boot. The former option is favored as far as maximum comfort is concerned. Again, this model is available in sizes 7 through 15, and the price ranges from $40 to all the way up to $115, depending on the exact specifications that you choose.

These are very similar to the Dansko shoe listed above in aesthetic, though the padded collar and more rugged rubber sole might allow for a cozier experience if you’re going to be doing an exceptionally high degree of walking throughout your day. Rockport has also put a lot into pushing what’s possible with air flow even further, making this a perfect candidate for those whose feet tend to get hot throughout the day.

 Bostonian Bolton Dress Slip-On

Bostonian Bolton Dress Slip-On

Bostonian Bolton Dress Slip-OnThe Bostonian Bolton Dress Slip-On is a modern iteration of an enduring classic design. Being something of a basic layout, the Bolton might not stand out from the crowd too much aesthetically – but among comparable shoes, it offers distinct function and its look is great. In fact, it would be hard to find a pair of slip on which could easily outclass the sophisticated look of the Bolton’s.

Lending to its comfort is the excellent shock absorbing, highly cushioned footbed that provides a smooth ride while walking and comfort while standing. The roomy toe box gives plenty of room to stretch the toes and helps to prevent cramps. On the bottom of the shoe, we find traction soles designed to keep your grip on where ever you’re standing. The contoured EVA outsole is lightweight, flexible and durable. The removable Flexlite EVA footbed provides comfort and support for on feet all day long. The removable footbed allows the insertion of orthotics for problem feet.

Perfect for adding a little extra formal touch to your casual attire, or as your main pair of loafers for dress clothing. The Bostonian Men’s Bolton Dress slip-on are sure to provide through the work week and beyond.

 Crocs Shaw Leather M Slip-On LoaferCrocs Shaw Leather M Slip-On Loafer

Crocs Shaw Leather M Slip-On LoaferCrocs, Inc., a rapidly growing designer in the industry has been able to create one of the most comfortable dress shoes for men in the Crocs Men’s Shaw Leather M Slip-On Loafer. The Croslite material has helped the manufacturer produce a comfortable, soft, lightweight, odor-resistant, superior-gripping, and non-marking pair of shoes. These elements make the Crocs Slip-On Loafer a pair of shoe ideal for casual wear. It is even great for professional as well as recreational wear such hiking, boating, gardening, and hospitality work. The shoes are versatile, comfortable, and lightweight at the same time. This has enabled the manufacturer to promote their shoes to a broad range of consumers. The removable insole, leather upper, and synthetic sole are some of the salient features of the product. This is why you need to choose Crocs Men’s Shaw Leather if you are looking for the most comfortable dress shoes for men.

 Mephisto Marlon Lace-Up

Mephisto Men's Marlon Lace-Up

The most expensive shoe on our list, this offers the finest walking shoe on earth. Comfort and support for tired, aching feet, this durable shoe is recognized as a shoe for those who are serious about looking for the most comfortable dress shoes for men standing all day. Handmade with leather, latex as well as cork and rubber. These high-quality shoes offer detailed stitching as well as outstanding craftsmanship. Breathable comfort and soft air technology let you feel as if you’re walking on air.

Mephisto is yet another brand that gives you comfort in the men’s walking shoe market. Their master shoemakers have given their brand the motto “The Finest Walking Shoes.” These are on the dressier end of the spectrum, as men who are going for a more sophisticated look choose them. Some of the Mephisto options are even designed for wear with a business suit.

No matter which look you choose with Mephisto, they all come with a patented Air Jet system. This permits air to flow through the entire shoe as you take every step. Your feet feel healthy and fresh, even if you have been walking all day. The uppers come with an Air-Relax technology allowing more breathability and durability. The Mephisto also features foot, arch and heel support based on the principles of correct anatomical design. With an air-cushioned sole, they have a look and feel that is ultra-light and sophisticated at the same time.

 Cole Haan Caldwell Lace-Up Shoe

Cole Haan Men's Caldwell Lace-Up Derby Shoe

Cole Haan Caldwell Lace-Up  Shoe is a real comfortable pair of 100% leather loafers. This imported shoe features a manmade sole and apron stitched toe. Excellent as the finishing touch to your most dashing formal attire, the Dalton 2 also offers a lot of comforts in addition to their stylish appeal. This is accomplished with the help of the 100% leather design, which lends itself to natural cushioning and comfortable feel. It also provides the flexible yet supportive soles that allow the foot to move freely within the loafer while still providing the support and cushioning expected from a good shoe.

Timberland PRO Five Star Slip-On Soft Toe Dress Shoe

Timberland PRO Five Star Hunt ShoeSlightly lower priced than the above-mentioned other shoes, this classic dress shoe works well with a coat and tie or your favorite faded jeans. Polished full-grain leather gives these a great look while the fiberglass shank offers full support, anti-fatigue technology provides comfort and the slip resistant outer sole is ideal for excellent traction even if you’re working on a slippery surface. So go ahead and put your best foot forward, your feet will thank you.

This Timberland model is a soft toe dress shoe sure to keep those dogs from barking after a long day of standing and walking. It slips right on as well, so you don’t even have to worry about one of the biggest pet peeves of your typical lower end dress shoe: laces that just won’t stay tied! The high-quality materials and synthetic sole also lend themselves to every step you take being absorbed consistently throughout, one of the prime factors in allowing for a comfortable shoe with adequate support. You can buy this shoe for as low as $80, though it can go as high as around $130 in some instances. Anyone between a size 7 and 15 can also enjoy these Timberlands, so you’re more than likely covered on all fronts!

Best Insoles for men’s dress shoes

Alternatively, you can try replacing the insoles with the best insoles for men’s dress shoes.

Birkenstock BirkoBalance Arch Support Insoles for dress shoes


If your feet gets tired due to standing all day and you have flat feet, then try these shoe inserts from Birkenstocks for your dress shoes. Made of cork, leather, and latex, they will mold to your feet shape over time and will provide you the support and stability that you need for standing long hours.

Footminders Casual Orthotic Arch Support Insoles for Dress Shoes

If you have foot pain due to plantar fasciitis from standing all day, Footminders insoles for dress shoes will provide heel pain relief. They are thin comfortable and durable insoles that you can use in a variety of shoes including dress shoes. They feature dual layer firm EVA supportive insole along with Durapontex layer for adequate arch support and cushioning. Also, they have a heel pad for added shock absorption. The deep heel cup provides rearfoot stability, support and cushioning for shock absorption that relieves the pain of plantar fasciitis. The metatarsal support will help in preventing the pain at the ball of the foot.


In this article, we’ve taken a look at some of the highlights of the most comfortable dress shoes for men standing all day. Hopefully, these selections will guide you to finding a pair of dress shoes that meets your needs both stylistically and functionally!

With any of the above models, you should be able to survive extended periods of time of time on your feet much easier than before. It’s true a lot of times that you really do get what you pay for, and a lot of people tend to spend as little as possible when it comes to dress shoes. They’re seen as a secondary item, so why throw all your resources at them, right? These offerings from Timberland, Dansko, Rockport, and Clarks prove that you don’t have to break the bank to actually feel good while dressing nice, however no matter which one you choose, your feet and ankles will absolutely be thanking you!


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