Most Comfortable Men’s Dress Shoes – 2022 Guide

A smart pair of dress shoes will make you feel stylish and comfortable when you step out of the door. But can you guarantee they are going to be comfortable all day long? Regardless of the occasion – whether you wear them every day or on one off events – your dress shoes need to be both classy and comfortable, complimenting your suit without leaving you in crippling pain. So in this guide, we are going to look at what makes the most comfortable men’s dress shoes, and some great reviews.


Most Comfortable Men’s Dress Shoes – Comparison Table

Product ImageProduct nameFeaturesMaterials

1) Cole Haan Men's Original Grand Shortwing Oxford ShoeEVA midsole

Fantastic pricepoint

Wingtip oxford in leather
100% Leather

Rubber sole

2) Rockport Men's Sharp and Ready Colben OxfordLightweight shock absorption

Reduce foot and leg fatigue

Latex foam footbed:
100% Leather

Synthetic sole

3) CLARKS Men's Escalade StepFlexible sole

Non-marking outsole

Breathable leather
100% Leather

Synthetic sole

4) Cole Haan Men's 2.Zerogrand Laser Wing OxfordFully padded sock lining for ultimate comfort

Fully rubber outsole with Grand OS technology

Dynamic energy foam
100% Leather

Rubber sole

5) Ecco Men's Helsinki Slip-OnRemovable leather insole

Direct injected

Features cow leather
100% Leather

Synthetic sole

6) Stacy Adams Men's Dunbar Wingtip Lace-Up OxfordBurnished brogue perforated trims

Blind-eyelet lacing

Lightweight construction
100% Leather

7) La Milano Wide Width Men's Leather Dress ShoesInnovative Comfortable Technology

Combination Full Leather Upper

Wide Width
100% Leather

8) Calvin Klein Men's Jameson Soft Leather/City Emboss Slip-On LoaferTimeless and sophisticated

Contrasting textured upper finished

Flexible construction
100% Leather

Rubber sole

9) Cole Haan Men's Original Grand Chukka BootChukka boot in leather uppers

EVA midsole with rubber outsole

Cushioned with Grand.OS technology
100% Leather

Rubber sole

10) CLARKS Men's Tilden Style Monk-Strap LoaferRemovable Ortholite footbed

Cushion Soft technology

Flexible TPR outsole
100% Leather

Synthetic sole


What should I look for in a comfortable dress shoe?

There are quite a few factors that go into making the decision about which dress shoe is right for you. You want the design to be smart and stylish, but often this can come without comfort from the shoe. Therefore, you’ll want to consider all aspects — the style, the interior construction, the heel, the sole and the size of the shoe when buying to ensure your pair of shoes are the perfect fit.


Traditionally, dress shoes are made from leather. Although you will often see dress shoes made out of other materials such as suede, leather is the go-to that keeps you looking smart. Black is normally considered more formal than brown leather, but it depends on what you are wearing with the shoe and the event you are attending. There are also different types of leather to choose from, including full-grain, top-grain, patent, and pebble grain.

Full-grain leather is superior to the other types of leather as it is durable, comfortable and moisture-resistant. Top-grain is also very good and patent leather, which gives the shoe a shiny look, is perfect for certain formal events such as a wedding. Pebble-grain leather is a material that gives a slightly rough, grainy feel to the shoe.


There are many different types of styles of dress shoes to choose from and it will be up to you to decide which is a comfortable style for you and which maths your outfit. A few include wingtips, brogues and loafers. Generally, dress shoes should be lace-up or slip-on to keep you looking your most smart.


Everyone has a unique foot and therefore it can be difficult when finding the right fit for your dress shoe that is still comfortable at the end of the day. You will need to know your size before buying your dress shoe as generally they do not have much stretch. If your shoes are too big you will likely get blisters while wearing the shoes, or if they are too small your feet will be cramped all day. You should take into consideration that your feet do swell during the day and therefore it may be advisable to try a size up initially.

The Heel

The heel is very important as it is responsible for protecting your foot and ankle from the ground by absorbing the shock waves as you walk. Without a decent heel, your feet will be very uncomfortable. It can be difficult to know which heel height is right for you and it has been advised that you choose a one inch heel to start if you are unsure what is right for your feet. Too big and the heel will take away from the shoe’s classiness, and too small and the shoe will look too casual.

The Sole

The sole contributes greatly to the overall comfort of the shoe. The soles of most men’s dress shoes are made of rubber, crepe, and leather. Rubber soles are known for their durability and their grip, but can take away form the smart look of the shoe. Crepe soles are a type of textured rubber, however these are known to wear away very easily. Leather soles are the classic type of sole for a dress shoe and feel comfortable on your feet. Unfortunately, they don’t always provide great grip of floors, especially wet floors if you are going to an event outside.

Shape Of The Toe

The shape of the toe in dress shoes should typically be rounded as this gives for the most professional, smart look. However, slightly squared toes on dress shoes can compliment a suit.

There’s a lot to think about when it comes to deciding what dress shoe is right for you and which one is going to be most comfortable. However, we have complied a list of the most comfortable dress shoes available to you on Amazon right now, so you can go to events looking confident and feeling great.

The Most Comfortable Men’s Dress Shoes

1) Cole Haan Men’s Original Grand Shortwing Oxford Shoe

The Original Grand Shortwing Oxford dress shoes from Cole Haan are one of the most popular men’s shoes from this brand. This shoe is crafted from soft leather and finished with brogue accents to give you not only great style but also maximum comfort. The sole is made from rubber and gives this shoe it’s durability to wear every day. With the classic look they give off, you will be able to wear these shoes to any event, whether it be every day to the office or a one off at a wedding. These also come in a black and different shades of brown, as well as a blue shade.

Key Features:

  • EVA midsole
  • Fantastic pricepoint
  • Wingtip oxford in leather




2) Rockport Men’s Sharp and Ready Colben Oxford

The 100% leather material and sleek design from the Rockport Men’s Sharp and Ready shoe makes for the perfect dress shoe. In the traditional Oxford design, this shoe comes in extended widths and sizes such as narrow and extra wide, so you can find the size that fits and keeps you comfortable when wearing them. These pair of shoes are lightweight so they minimize foot fatigue when you need to wear them for a long periods of time. The shock absorption features and the latex foam footbed also help to keep your feet from feeling tired, and the soft lining cushions your foot as you walk. They’re also incredibly flexible and move to accommodate your foot, meaning you can with confidence and comfort. These dress shoes come in a range of colors and materials, including suede.

Key Features:

  • Lightweight shock absorption
  • Reduce foot and leg fatigue
  • Latex foam footbed




3) CLARKS Men’s Escalade Step

The Escalade Step from Clarks gives you an easy slip-on dress shoe that still has the class of a lace-up shoe. The material is 100% leather and the shoe features a padded collar and stretch gore to fit around your foot and leave you feeling as comfortable as possible. Inside, a leather and mesh footbed cushions the foot too. The flexible soles and small heel have no traction issues so you don’t need to worry about slipping when wearing these shoes. They come in both a black and a brown leather, so you can choose the pair that’s right for your event.

Key Features:

  • Flexible sole
  • Non-marking outsole
  • Breathable leather




4) Cole Haan Men’s 2.Zerogrand Laser Wing Oxford

These men’s shoes from Cole Haan give a twist on traditional dress shoes by combining the style of an Oxford shoe with hints of an athletic running shoe. The laser wing design on top of the shoe allows for a sophisticated look, combined with the soft rubber sole that gives great traction and leaves you feeling supported. A fully padded sock lining offers you ultimate comfort, encasing your foot breathable material. These comfortable shoes are available in a variety of colors and styles – including textured leather and suede.

Key Features:

  • Fully padded sock lining for ultimate comfort
  • Fully rubber outsole with Grand OS technology
  • Dynamic energy foam




5) Ecco Men’s Helsinki Slip-On

The Ecco Helsinki dress shoes are an easy slip-on, but still look sleek for whatever event you are attending. Made from 100% leather, this shoe is sturdy yet allows your foot to flex and moves with you as you walk. The tapered bicycle toe stitching and softly squared toe create a sophisticated look and a padded insole with contoured heel cushion and arch support keeps you feeling comfortable all day. The insole is also ventilated and creates circulation around your foot, so you don’t need to worry about your feet becoming too hot whilst wearing these shoes. The sole, with a reasonable heel, is designed for flexibility and shock absorption. These are also available in a black and darker brown.

Key Features:

  • Removable leather insole
  • Direct injected
  • Features cow leather




6) Stacy Adams Men’s Dunbar Wingtip Lace-Up Oxford

The Oxford style of these Stacy Adams dress shoes offer a classic look with a wingtip design and burnished brogue perforated trims. Also available in a black, blue and darker brown, these shoes give you maximum comfort with their memory foam insole that curves to your foot and keeps your supported and comfortable for the duration of the wear. This also helps with shock absorption when you walk, alongside the flexible sole and low heel. The shoes are lightweight but durable, so are great if you are looking for an everyday dress shoe too.

Key Features:

  • Burnished brogue perforated trims
  • Blind-eyelet lacing
  • Lightweight construction




7) La Milano Wide Width Men’s Leather Dress Shoes

The combination of soft leather and pebbled leather in the La Milano men’s shoes means not only do they look smart, but they’re super comfortable too. The pebbled leather offers great support when walking and also minimizes creases, so your shoes stay looking new for longer. The padded collar around the heel adds to the comfort of these dress shoes, as does the memory foam insole and latex heel cushion that protect your feet as you walk. Deigned for those with larger feet, these shoes run wide, so if you are on the smaller side you might want to order half a size down.

Key Features:

  • Innovative Comfortable Technology
  • Combination Full Leather Upper
  • Wide Width




8) Calvin Klein Men’s Jameson Soft Leather/City Emboss Slip-On Loafer

Calvin Klein’s Jameson loafers are easy to slip on and are flexible, moving with your body as your walk and absorbing any shock waves with the cushioned foam insole. Giving a sophisticated look, the slight heel on these shoes supports not only your foot but also your ankles and legs to stop them from feeling tired. Crafted from leather, the soft leather is contrasted with the textured leather and finished with Calvin Klein branded hardware. Providing maximum comfort for wherever you’re going, the leather gives you the freedom to move without feeling any discomfort.

Key Features:

  • Timeless and sophisticated
  • Contrasting textured upper finished
  • Flexible construction




9) Cole Haan Men’s Original Grand Chukka Boot

The dress shoe is a little different, as it comes in the form of a boot rather than an Oxford shoe or a loafer. The Cole Haan Chukka Boot is made of smooth leather with a contrasting sole that stands out for maximum sophistication. The slightly cushioned insole and soft lining made of textile gives you great comfort as you walk. With a rubber sole, your feet are cushioned as you walk and the shoes are unlikely to slip. These boots can be worn not just as dress shoes, but also everyday with jeans or other pants. They’re also available in a darker brown and a black.

Key Features:

  • Chukka boot in leather uppers
  • EVA midsole with rubber outsole
  • Cushioned with Grand.OS technology




10) CLARKS Men’s Tilden Style Monk-Strap Loafer

The Tilden style dress shoes from Clarks are crafted from full-grain leather and offer immense comfort with the removable OrthoLite® footbed with cushioning technology, meaning your feet feel great all day long. The single monk-strap buckle adds a classy feature to your dress shoes to make you feel sophisticated at any event. The small heel and soles are made from durable rubber and protect the feet by absorbing any shockwaves, as well as providing flexibility in the shoe so you can move around with no problem. These comfortable shoes look great paired with a suit, or add an extra hint of style to jeans or chinos.

Key Features:

  • Removable Ortholite footbed
  • Cushion Soft technology
  • Flexible TPR outsole





It can be difficult to find a dress shoe when there are so many options out there. You must take into consideration the style, the material, the sole and the fit of the shoe to ensure you are going to be comfortable. Whether you’re at the office all day or wearing the shoes to an event, a good pair of dress shoes can help you to look and feel your best. We hope that above you can find a dress shoe that not only compliments your outfit, but keeps you supported and comfortable all day.