Most Comfortable Dress Shoes for Men

Every guy need a great pair of dress shoes in their closet. At one point in their life they will need to suit up, even if it is not the required outfit for their career choice. Unfortunately, most dress shoes seem to be uncomfortable, with stiff materials and a narrow toe box. The key is to know what to look for when purchasing dress shoes so you can find the most comfortable pair.

Anatomy of the Dress Shoe

Dress shoes are not like other shoes, they have a lot more features in them. A comfortable dress shoe is typically made up of four parts; toe box, vamp, facing, and the quarter. The toe box is where your toes will be resting in while wearing the shoe, while most dress shoes are narrow, the most comfortable will have a wider toe box. The vamp is the area just below the toe box. This area is where a dress shoe will typically get wider as your foot is also wider in this area. But the materials on the vamp can be still, causing this area to feel tight for some people. The facing is where the shoe strings are located. And the quarter is the area located on the side right before the heel. This area should provide stability as well as comfort.

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What to Look For

If you have a profession that requires you to be on your feet all day long, more than likely you know that it can cause back, leg, and foot pain. Making sure that you have a supportive and comfortable shoe to prevent these injuries is an important part of contributing to your overall health. While most dress shoes may not look comfortable, it is important to look for certain aspects that can provide a more comfort while wearing a dress shoe.

  • Wider Toe Box

Most dress shoes have a narrow toe box. When you toes are unable to move and your feet feel cramped it can cause pain throughout the whole body, especially if you are on your feet all day long. There are many different toe styles available for dress shoes, some are wider than others. If you are looking for a dress shoe with a wider toe box look for cap toe, apron toe or split toes, these are typically found on loafer. Not to say that other styles of dress shoes may have wider toe boxes.

  • Breathable

Dress shoes are typically made from leather. While leather may look nice, the material alone is not very breathable. Some dress shoes may have multiple materials that are engineered together to provide a better breathability for your feet.

  • Support

Typically, a dress shoe is not designed with comfort in mind, instead they are made to appease style and sophistication. It is important to find a dress shoe that has arch support and cushioning to provide comfort. An uncomfortable shoe is not a good shoe.

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Top Ten Most Comfortable Dress Shoes for Men

1. ECCO Helsinki Cap-Toe Oxford Dress Shoe

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The ECCO Helsinki Cap-Toe Oxford provides both style and comfort. Available in black or brown colors, it can be paired with any pair of slacks and look good. The leather upper is moisture wicking allowing your feet to stay dry and clean. The cap toe style provides a wider area for your toes to move around in making the shoe more comfortable all around and gives it a refined look. With removeable insoles, these shoes are customizable to your own comfort level and the polyurethane outer sole provides arch support, cushioning, and absorbs any shock that may occur. These ECCO shoes are roomy, stylish, and will provide your foot with all day comfort.

2. Hush Puppies Leverage

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Hush Puppies shoes have been around for a long time and are best known for their style and comfort, and the Leverage is no exception. With a slip-on style, the Leverage provides comfort and support. This shoe has a breathable textile lining that will keep your foot dry as well as a leather waterproof upper. The trademarked Zero G technology makes these shoes lightweight and great for all day wear, without causing any additional strains to your legs and feet. They can be dressed up with a pair of slacks or dressed down with a pair of jeans. But overall, they are incredibly comfortable.

3. Clarks UnSheridan Slip on Dress Shoes

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When you don’t have time to bother with shoe laces and still want a comfortable shoe the Clarks UnSheridan Slip On dress shoes are the way to go. Made with a ventilation system to keep your feet dry and cool these leather shoes are stylish and relaxed. They are engineered with lambskin lining which provides extra flexibility and support, plus no break in time needed, like most other leather shoes. With all the great features of the Clarks UnSheridan Slip On dress shoes you can expect to spend a pretty penny on these.

4. New Balance Dunham

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New Balance mixed dress shoes with stability shoes and created The Dunham. Designed with a leather upper these shoes offer a classic look. The rounded toe box gives a spacious amount of room for your toes to move around in and allow for the circulation to keep flowing. The textile lining and plush ABZORB cushioning provides an extra level of comfort. Plus these shoes are approved by Medicare for Diabetic feet.

5. Dankso Walker Oxford

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Engineered with genuine leather and a slip resistant rubber sole, the construction of these shoes provide comfort and durability. The leather is moisture wicking so they can stay clean easily by wiping them off with a clean damp cloth. With padded arch support and breathable lining the Dankso Walker Oxford dress shoes are great for being on your feet all day. Plus, the rounded toe works in both casual and dressy settings.

6. Rockport Northfield Waterproof Oxford

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The Oxford is the original dress shoe so it is no wonder that Rockport made their own variation on this timeless staple. Even though this shoe looks stiff and bulky, the padded collar offers a sense of comfort around the entire ankle, while the insole provides cloud-like padding around the foot. The rubberized sole on the bottom is durable and absorbs shock to reduce injury.

7. Bostonian Men’s Bolton Dress Slip-On

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Another variation on the dress shoe is the Bostonian Men’s Bolton Slip-on. Available in both black and brown leather, the slip-on feature is great because these are shoes you will want to waste no time putting on. With a square toe box, there is plenty of wiggle room for your toes to help prevent cramps and circulation issues. The traction on the soles keep your grip and prevent you from falling or causing injuries. As far as the comfort level is concerned, the Flexlite EVA foot bed provides an exceptional amount of padding to make being on your feet all day bearable.

8. Crocs Santa Cruz 2 Luxe Loafer

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Don’t let the brand name fool you, these are not your typical Crocs that you see nurses and children wearing. These Slip-On Loafers do not have small holes all over them to provide breathability but the leather that it is created out of does provide some ventilation to keep your feet cool and dry, which makes them odor resistant. The slip resistant and shock absorbing sole make these safe and comfortable to wear.

9. Timberland PRO Slip-On Soft Toe Dress Shoe

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Made from full grain leather and available in brown, these shoes are less inexpensive than most others on this list, and still have excellent support and comfort. The soft toe provides extra room in the toe box giving it the greatest comfort level possible. Plus, the traction on the bottom makes these shoes slip resistant, even on wet or icy surfaces. Every step has shock absorption making these great for all day wear.

10. Mephisto Men’s Marlon Lace-Up

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If you have a never ending budget when it comes to buying shoes, perhaps the Mephisto Men’s Marlon Lace-Up is the shoe for you. Available in a black pebble grain and chestnut pebble grain these shoes are stylish, luxurious, and comfortable. Handmade with leather, latex, cork, and rubber, these shoes are high-quality and go all out. With soft air technology, they are breathable and keep your feet cool, dry, and odor free. You definitely get what you pay for when purchasing the Mephisto Marlon Lace-Up shoes. While your wallet may be crying in pain, your feet will thank you.

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