The Top 10 Most Comfortable Dress Shoes for Men in 2022
After reviewing 34 products, the Calvin Klein Brodies are the most comfortable dress shoes for men.
In order to find the most comfortable dress shoes for men, we reviewed 34 pairs of shoes. We looked for cushioning, softness, and flexibility to decide which dress shoes are the most comfortable.
Being a bit of a shoe-addict, I know that ‘men’s dress shoes’ and ‘comfortable’ don’t always go together. However, comfortable dress shoes do exist! And that’s what we’ll be talking about today.
The Calvin Klein Brodie Oxford Shoe is our team’s top overall choice. This shoe is versatile and classic. If you just need a dress shoe to have on hand for interviews, meetings, weddings, and other special occasions, these will do the job.
Because we know how important comfort is, we looked at more than just looks. The Calvin Klein Brodie Oxford has a foam insole, a roomy toe box, and a soft nappa leather upper. No matter what the occasion, your feet will be able to stay in these shoes all day.
After speaking to stylists and testing shoes in-store, we do understand everyone is different. If you want a penny loafer, get the Rockport Classic Penny Loafer. If you want a smart-but-comfy Chukka boot, we recommend the Clarks Men’s Paulson Mid Chukka Boot.
To find out more about these products and our other top choices, read on!
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Table of Contents
Most Comfortable Dress Shoes for Men
Calvin Klein Brodie Oxford Shoe
Why this product?
Lightweight Nappa leather for a timeless look. Crease-proof and flexible design. Durable synthetic rocker sole with a one-inch heel for a natural posture. Supportive foam insole with cushioning and roomy square toe. Available from sizes seven to sixteen.
When it comes to a comfortable dress shoe, the Calvin Klein Brodie Oxford shines. The quality, timeless look of this shoe will work for countless occasions and uses. The comfortable, flexible design ensures that you won’t be wearing the shoes through gritted teeth.
The Brodie Oxford is made with nappa leather, a soft, lightweight leather not often seen in men’s dress shoes. It’s unwaxed and takes a bit of extra care to maintain, but the quality and shine are worth it. Napa leather isn’t prone to creasing.
The leather upper is balanced into a very standard, versatile dress shoe. It has a simple lace-up system and a rounded square toe. The synthetic sole is durable with a one inch heel.
If you’re worried about the heel, know that this is a rocker sole. This means the toe feels level with the heel in a natural and comfortable posture. The sole is also flexible to give you a range of motion as you go through your day.
Although this shoe is definitely a dress shoe, it’s also a comfortable shoe. These come in shades of black and brown to fit your needs in a timeless look. They are easy to wear, whether you’ve owned several dress shoes or are choosing your first pair.
Let me focus a little more on comfort for a moment. The foam insole has some cushioning to support your foot without impairing mobility. The square toe is roomy, and the shoes come in options of medium or wide and sizes seven to sixteen.
For an inexpensive, classic dress shoe, these Brodie Oxfords from Calvin Klein are hard to beat, which is why we chose it as our number one pick.
- Soft and lightweight nappa leather
- Durable synthetic sole
- Easy to wear
- Takes extra care to maintain
Most Comfortable Oxfords for Men
Clarks Tilden Cap Oxford Shoe
Why this product?
A comfy classic shoe for everyday wear. Luxurious Ortholite footbed for all-day comfort. Flexible sole from thermoplastic rubber that’s wear and tear-resistant. Non-marking full-grain leather upper offers flexibility—incredibly soft heel pad.
If you’re on the market for a pair of nice dress shoes that are comfortable enough to wear every day to work, try these Tilden Cap Oxford shoes from Clarks. This shoe isn’t focused on looking good, though it certainly has a classic appearance. Instead, it is a shoe that’s all about comfort and wearability.
The Tilden Cap Oxford has an Ortholite footbed. This soft foam molds to your foot and provides excellent cushioning throughout the day. The footbed is amazing, providing all day comfort. If you’ve worn many dress shoes, you know how much of a luxury a soft footbed can be!
To balance out the footbed, the Tilden Cap Oxford shoe has a flexible sole made of thermoplastic rubber, or TPR. It’s highly durable and resistant to wear and tear. In order to increase comfort even more, Clarks included a polyurethane (PU) lining throughout the shoe.
The full-grain leather upper is non-marking and a decent quality, especially for the low price. The upper offers some give, which adds flexibility and makes these shoes even easier to wear.
The one-inch heel looks elevated, but thanks to a rocker sole design, is at the same level as the toe box. The square toe box gives plenty of room. In addition, the shoes come with low-profile gore panels which give a better fit without taking away from the classic look.
Overall these are a great, classic cap toe derby. The heel and footbed are where the shoe really shine. Not only will these look professional and classy, but more importantly, they will be comfortable. Say goodbye to pinched toes or aching heels with this Ortholite cushioned footbed and incredibly soft heel pad.
- Ortholite footbed offers cushioning
- Durable thermoplastic rubber sole
- Full-grain leather upper adds flexibility
- Not the classiest-looking
Most Comfortable Dress Shoes for Men
Cole Haan Original Grand Shortwing Oxford Shoe
Why this product?
Sole designed with a flexible bend for natural walking gait. Layers of cushioning foam in EVA midsole for ultimate comfort. Durable Nubuck leather upper that’ll make you stand out. Roomy toe box and excellent breathability. Suitable for all occasions.
Cole Haan is well known for making comfortable, affordable shoes that still qualify as dress shoes. The Original Grand Shortwing Oxford is no exception. With brogue elements and a highly cushioned outsole, these are a perfect combination of style and comfort.
The Original Grand Shortwing Oxford is comfortable in every aspect. The sole is designed with a flexible bend that moves with your natural walking gait. The EVA midsole offers layers of cushioning foam, and the insole and footbed are both incredibly comfortable.
A first look at the shoe will probably leave you wondering at the sole. While visually, the thick rubber sole may be a bit much, in terms of comfort it’s worth it.
The athletic appearance of the sole, however, is balanced by the upper. The upper is made of Nubuck leather, a more durable, sturdy leather made similarly to suede. The shoe really stands out, however, thanks to the brogue elements.
Brogue shoes are made of leather and decorated with perforations and serrated exposed edgest. The look is classic and interesting, and works well even with the thicker sole of the Original Grand Shortwing Oxfords.
The toe box is roomy and the shoe feels breathable. It’s not everyday that you find a shoe that looks stylish but is as comfortable and easy to wear as these. They can easily become a solid go-to for wearing to work, to dates, and even to formal events.
- Interesting design with brogue elements
- Nubuck leather makes it durable and sturdy
- Highly breathable
- Not for people who want to blend in
Most Comfortable Penny Loafer for Men
Rockport Classic Penny Loafer
Why this product?
Convenient slip-on design for people on the go. Versatile and goes with any wardrobe. Easy to clean, durable, and sturdy full-grain leather uppers. Rockport’s truTECH for shock-absorption. Removable EVA footbed for stability and comfort. Available from sizes six to fifteen.
The Rockport Classic Penny Loafer is so comfortable you may have a hard time believing it’s a dress shoe. With sizes six to fifteen and options for normal or wide, you can find a great fit that will work for endless occasions.
The slip-on design of this Loafer makes it super easy to slip on and off. It’s also great for dressing up with a suit or dressing down. In fact, you can even wear this shoe with khakis or shorts for a casual but comfortable look.
For such a low price point, this penny loafer comes with a lot of upsides. The full-grain leather uppers are sturdy, easy to clean, and durable.
One point against this shoe is the cement construction of the sole. Though often marketing as being more durable and sturdy, cement construction also means that you cannot re-sole this shoe once it wears out.
However, it’s hard to complain for the price point. Plus, the polyurethane outsole is made with Rockport’s truTECH, a shock-absorption feature that also adds extra cushioning to the heel. The shoes also come with a removable EVA footbed which is very comfortable and highly stable.
The penny loafer style is highly comfortable and convenient. The leather upper of the Rockport Classic Penny Loafer makes it styles and dressy, while the EVA footbed and flexible sole make it perfect for an everyday shoe that can be dressed up or down depending on your situation.
- Easy slip-on design
- Easy to clean full-grain leather uppers
- Incredible shock-absorption
- Can’t resole the shoe
Most Comfortable Monk Strap Shoe for Men
La Milano Double Monk Strap Slip on Loafer
Why this product?
Smooth Argentine leather for an exquisite appearance. Durable leather for the price. Soft synthetic lining and memory foam insole for comfort. Stacked heel from wood and rubber for stability and grip across surfaces. Best value for money.
Monk strap loafers are another excellent choice of men’s dress shoe. For the most part, a single monk strap is considered to be more formal than the double monk strap. We choose to feature this double monk strap design because of its versatility.
The smooth Argentine leather elevates this shoe to a level of formality that will work for most big events and special occasions. The leather is excellent quality for a low price; it’s the best value-for-money included in this list.
Although this shoe is on the cheaper end, the leather can still be incredibly durable with the right care. You can use a shoe wax to regularly clean and shine these monk strap loafers.
The leather does come a little stiff. These shoes may require a short break in period. In addition, it’s important that you use a shoe tree to help these maintain their shape and stretch a bit when you aren’t wearing them. Then again, you should be using a shoe tree with any nice dress shoes.
As far as comfort goes, the La Milano Double Monk Strap Slip on Loafer has a soft synthetic lining in the interior. The insole is comfortable and made of memory foam, so it will adjust to your foot as you wear it.
The stacked heel has elements of wood and rubber. The rubber provides grip across surfaces, while the wooden heel gives stability, durability, and an extra touch of elegance. Overall, these are a brilliantly made shoe with a solid design that can be dressed up or down for any occasion.
- Argentine leather makes it look classy
- Memory foam insole for comfort
- Rubber in stacked heel minimize slipping
- Leather is a bit stiff
Most Comfortable Tassel Loafer for Men
Sperry Gold Cup Exeter Tassel Penny Loafer
Why this product?
Non-slip soles for extra security. High-quality leather is durable and smooth with hand-rolled and hand-sewn tassels. You can wear it with or without socks thanks to soft lambskin leather. EVA foam footbed for comfort and springiness. Wave-Siping technology for anti-slip.
Sperry combines the classic style of a dress shoe with comfort you can wear daily. They step up the quality another notch by adding non-slip soles for more security as you go through your day. Whether you need these dress shoes for a fancy boat party, a wedding, or a day at work, there are plenty of reasons to love these.
The Gold Cup Exeter Tassel Penny Loafer is a beautiful shoe with high quality leather. It’s smooth and durable and elegant. The tassels are hand-rolled and hand-sewn, as are other elements of the shoe. Due to its stunning, yet convenient design, this shoe is also suitable for work.
In order to make these shoes more comfortable, the inside is lined with lambskin leather. It’s soft and smooth and can be worn with or without socks for a more casual look.
The footbed is made of EVA foam and is springy and comfortable. The sole has a bit more of an athletic design, something that adds comfort. It’s a rubber sole with Sperry’s Wave-Siping technology. Using small slits in the outsole and larger wavy grooves, it has excellent anti-slip properties. Water will run through the grooves, leaving you on your feet and safe.
The Exeter Penny Loafer is also a great fit. It comes in sizes seven to fourteen, unfortunately with no wide options. The loop that circles the heel keeps the shoe secure on your foot while maintaining the ease of wear penny loafers are known for.
Overall, this is a great, comfortable tassel loafer. Though a bit chunkier than other dress shoes, it is comfortable and secure. The tassel adds a unique element and the smooth leather makes it easy to dress up or down.
- Unique look with hand-sewn tassels
- Smooth inside lined with lambskin leather
- Anti-slip properties
- No wide options
Most Comfortable Dress Boot for Men
Thursday Boot Company Captain Lace-up Boot
Why this product?
Durable and excellent quality leather. Goodyear Welt Construction treated for water resistance and added support. Cork-bed midsoles form to the feet. The insoles have shock-absorbing properties for extra protection. Odor reduction due to Poron antimicrobial cushioning.
Thursday Boot Company should be a go-to place to shop if you’re looking for a pair of dressy yet comfortable boots. While boots can’t easily be worn with shorts, they can be dressed up or down for a versatile and easy-to-wear shoe.
The quality of Thursday Boots is definitely worth noting. Although these dress shoes are a little more expensive than others on the list, you’ll see the price reflected in the excellent leather and the durability of these boots. The leather can last decades with proper care, and the soles can be changed to increase the lifespan of the Captain Lace-Up Boot.
In order to increase the longevity even more, the boots are treated with Goodyear Welt Construction which offers some water-resistance and an overall improvement in support and durability.
In terms of comfort, Thursday Boot Company has really focused on making these a pair of shoes you can wear all day. The cork-bed midsoles form to your feet, and shock-absorbing insoles means your feet have extra protection.
The insoles also use Poron antimicrobial cushioning to reduce odors and add more breathability. Finally, DuraEVA comfort strips add even more cushioning in key areas for all-day comfort. Plus, the Captain Boot is lined with a Supple Glove Leather interior for additional softness.
This classic design, with a minimalist cap-toe and waxed cotton laces is dressy but easy to wear. The studded rubber outsoles provide good grip on a variety of surfaces, and the leather upper just looks better with age.
- Shock-absorbing insoles
- Breathable and odor-proof
- Difficult to wear with shorts
Most Comfortable Chukka Boot for Men
Clarks Paulson Mid Chukka Boot
Why this product?
Low-ankle and sleek style for all occasions. Ortholite footbed has shock absorption properties. Stability and comfort thanks to the ankle collar. Thermoplastic rubber outsole for increased longevity. Sewn-on flexible sole with exceptional stitching. Breathable twill fabric lining.
Another style of dress boot is the Chukka Boot. This sleek, low-ankle style can look very formal or very casual, depending on how you dress it up. The lace-up style is simple but elegant and easy to wear.
The Clarks Paulson Chukka Boot is inexpensive and we found it to be incredibly comfortable. This is due in part to the Ortholite footbed, which has shock absorption and great cushioning. The ankle collar is also comfortable and offers great stability, and the lace-up design makes it easy to adjust these to your feet.
The Clarks Paulson Mid Chukka Boot comes in sizes seven to thirteen and a few color variations. Unfortunately it does not have a wide option, but also isn’t especially narrow.
The outsole of these Chukka boots is made of thermoplastic rubber, a type of rubber designed for increased longevity and durability. It’s a flexible yet sturdy sole and is sewn on rather than glued. The stitching is well-done and durable.
In order to increase comfort even further, these are lined with a twill fabric which is breathable and soft. The lining cushions your feet while you wear them but is breathable enough for odor control and temperate moderation.
The Chukka boot is a sleek, versatile option. It’s a little less more formal than a traditional lace-up boot or a Chelsea boot but can still be dressed up for big events.
- Excellent cushioning and shock absorption
- Flexible and sturdy sole
- No wide option
Most Comfortable Chelsea Boot for Men
Skechers Bregman-Morago Chelsea Boot
Why this product?
Work-appropriate, casual, yet classy. Supportive footbed with air-cooled memory foam for breathability. Shock-absorbing technology keeps foot pain at bay. Soft Goga Mat Arch adds cushioning and lightness. Minimized slipping due to rubber outsole with grooves for traction.
The Bregman-Morago Chelsea Boot from Skechers is comfortable, casual, and classy. These Chelsea boots tend to lean toward the more casual end of fashion, but they can still be dressed up as well. These are a great option for a wear-to-work-everyday boot.
The boots have a supportive footbed with air-cooled memory foam that enhances ventilation and breathability. The midsole uses shock-absorbing technology to save you from foot pain. Finally, Skechers uses a Goga Mat Arch to really focus on comfort. The Goga Mat is a soft, springy cushion that lasts longer and is much lighter on your feet than memory foam.
The leather upper is soft and has a slight burnished finish for a more versatile look. A pull on tab at the ankle and elastic panels on each side make these easy to slide on and off, and a comfortable fit once they’re on.
The rounded toe front gives these universal appeal. Stitching accents give it some character and formality. Overall, it’s a nice looking, easy-to-wear boot.
The outsole is rubber, with grooves for traction and a flexible design. These boots should do well on a variety of surfaces, with little to no slipping.
Because of these comfort features, the Chelsea boot is a great option for a daily shoe. These come in a couple different colors so you can match to your best outfits. They really can be made to look as formal as you need!
One thing to note is that many reviewers had the experience of needing to size down a half size. The elastic panels will stretch some overtime, so you want to make sure you get the right fit at the beginning.
For a more casual, comfortable look you can wear every day, try the Skechers Bregman-Morano Chelsea Boots.
- Enhanced ventilation and breathability
- Goga Mat Arch makes you feel light
- Available in different colors
- Elastic panels stretch overtime
Most Comfortable Smart Casual Shoe for Men
Cole Haan Grand Crosscourt Turf Sneaker
Why this product?
Sleek design with a smooth leather upper for all-day comfort. Durable insole with Oxford-style cut for endless uses. EVA outsole provides a good dose of cushioning. Rubber pads provide secure grip and traction. Suitable for any occasion.
This final shoe on the list is a perfect shoe for when you want to be comfortable but need to look good. If you didn’t expect to see a sneaker on the list, don’t worry! The Cole Haan Grand Crosscourt Sneaker is definitely not your average sneaker.
Made with a smooth leather upper and sleek design, this shoe can easily be dressed up for that important meeting or dinner out. However, since it isn’t your typical dress shoe, it will feel comfortable and casual on your feet.
Because these have a comfortable and durable insole, as well as an Oxford-style cut, they have endless uses. You could wear these sneakers to work for many jobs or you can wear them in your free time when you want to look a step above the lazy jeans, t-shirt, and sneaker days of your past.
These have a comfortable insole and EVA outsole which provide adequate cushioning. The sole is mostly injection molded with rubber pads at the heel and forefoot. The added rubber provides secure grip and traction, which the rest of the outsole is flexible and lightweight.
Even with the low price point, we found these shoes to be of great quality. You may find yourself slipping into these sneakers every time you don’t need to wear dressier shoes. These are a comfortable everyday shoe but a big step up from sneakers or canvas top shoes in terms of style.
- Durable insole for comfort
- Can be styled with a t-shirt or a suit
- EVA outsole provides amazing cushioning
- Not the classiest on this list
What to look for when buying this type of product
Since this article is about dress shoes, we need to first address the issue of style. There are a few different types of dress shoes, from oxfords to loafers to boots.
A good dress shoe should be a neutral color, such as brown or black. It should be made of leather, though the exact leather used can vary from nubuck to napa to suede.
Finally, a good dress shoe should have a moderately thick sole. The sole should not stand out dramatically or be so thin that it doesn’t last. The sole can be made of leather as well, but more commonly it is rubber for added durability.
Unfortunately, dress shoes are notorious for having very little padding. Irregularities in the shoe, or even normal stitching, can rub and press against your feet. Compounding the problem, many dress socks are made quite thin.
In order to find the most comfortable dress shoes, we looked for shoes that do include padding, especially around the ankle collar. If you can’t find the right fit with proper padding, you should at least look for a soft lining that will protect your foot.
To focus on comfortable dress shoes, we also focused on cushioning. Although you might think the footbed is the only element that matters here, the truth is all the parts add up.
Good cushioning begins in the outsole and extends through the midsole and insole. Whether the shoe has orthotic insoles or memory foam, it should conform to your foot as you wear it.
In a well cushioned shoe, the outsole is rubbery and light. Outsoles with a bit of bounce give you relief on hard surfaces or after long periods of wearing the shoe.
Besides comfort, another element often excluded from dress shoes is breathability. If you need to wear dress shoes in difficult weather or hot conditions, you’re out of luck.
Sweat can lead to discomfort, pain, odors, and blisters. To avoid this problem, we chose shoes that are well ventilated with moisture-wicking and, in some cases, antibacterial properties.
This feature may sound obvious but it’s so important. Comfortable dress shoes should fit your feet well. Sometimes the right length and width are blocked by the design.
Because of this, we chose shoes with wide toe boxes, relaxed fits, and orthopedic designs. We tend to prefer brands with experience in athletic footwear, as they are more likely to have experience making shoes that perfectly fit men’s feet.
The final element to consider is durability. How much will this shoe last? This is an important factor to consider in purchasing any shoe, but it matters especially in dress shoes. Men’s dress shoes tend to be expensive, so you want them to last.
You want a sole that is made of a durable material, like leather. More importantly, you want a shoe that does not have the sole cemented on, since that means you won’t be able to replace the sole if it wears out before the rest of the shoe.
Choosing the best, most comfortable men’s dress shoes is not a task we took lightly. After trying on thirty pairs of shoes, walking around in them, and looking at key elements, we’ve made our decision.
The Calvin Kleins Brodie Oxford ticks all the boxes. Comfortable and stylish, versatile and easy to wear. This shoe has lasting cushioning and stability. It’s sleek leather upper makes it a good choice no matter how formal or casual you need.
In order to make the shoe-choosing process a little easier for you, we’ve included links with each shoe on the list. Just click the shoe you love and find it in your size! With a good pair of dress shoes that don’t hurt your feet, dressing up is about to become much easier.
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