How to Choose Comfortable Dress Shoes for Men

Dress shoes are often synonymous with looking good, but not always with feeling good—at least, not until the recent past. With many comfortable dress shoes for men having hit the market in recent years, including orthopedic options, men no longer have to sacrifice comfort for style or professionalism. However, even with supportive men's dress shoes readily available, knowing how to choose comfortable shoes can be more difficult than it seems. Follow our seven suggestions below to find the perfect pair that will keep you looking and feeling your best all day.

  measuring foot size

1. Know your feet measurements.

The first step to choosing comfortable dress shoes for men is selecting the right fit, and in order to do that you must know your measurements. Sizes can vary from brand to brand, and differences in shape depending on the type of shoe can make minor discrepancies in sizes even more pronounced. For instance, if you're looking for comfortable leather shoes, knowing your general sneaker size does not guarantee that an Oxford shoe in that size will fit the same way. You can measure your feet on your own at home using a tape measure, or you can use the metal devices commonly found at shoe stores the next time you’re out shopping. If you’re struggling to measure your feet on your own, you can seek out a shoe professional to help you out.

2. Try out a wider shoe.

How should dress shoes fit? Men's dress shoes are often made of leather, which stretches slightly over time. While comfortable leather shoes will loosen a bit after you break them in, you should still avoid buying shoes that are too tight across the laces (or across the top of the foot, if the shoe doesn’t have laces). A common mistake people make is automatically sizing up when a shoe is too tight, but in many cases, you simply need a wider version of the same size. Feet usually widen as we age, and you may find that a wide fit shoe feels better, especially if you find yourself often keeping the laces loose. Men’s extra wide dress shoes give you the width you need across the foot so you can walk in comfort, without your foot sliding around in a too-long shoe.

adjusting orthotics sole 

3. Don’t ignore arch support.

No matter how great a shoe looks, it will be extremely uncomfortable to wear if it doesn’t provide the proper arch support. Finding comfortable men's dress shoes with sufficient arch support is especially important for those with plantar fasciitis, as this involves inflammation of the tendon along the bottom arch of your foot. Properly supportive shoes can help treat plantar fasciitis pain in the short-term and even prevent it in the long run. As you try on shoes, be honest with yourself about whether they give you enough cushion. If a pair is lacking, you can also add special inserts for additional support (more on this below).

4. Make sure the heel doesn’t slip.

Blisters, rubbed skin, and other unpleasant minor injuries are often caused by shoes that are too loose and thus chafe against the skin. When trying on shoes, be sure to test them with the type of socks you would normally wear them with and walk around to determine if the heels slip or not. When in doubt, opt for a thinner sock, as a thicker sock can artificially pad the heel so you won’t be able to tell how much of it really moves.

5. Watch out for thick seams.

When shopping for men's comfortable dress shoes, be mindful of cases of fashion over function. While thick seams and lots of top stitching add a decorative touch to dress shoes, they can cut into your foot as you walk if the leather and stitching are stiff enough. Not every dress shoe with distinctive seams has this problem, especially if the leather has been treated so it’s on the softer side, but if the shoe has a lot of stitching, it’s worth trying it on and bending it to make sure the seams conform to your foot rather than cut into it

 dress shoes

6. Look for adjustable features.

The shape and size of your feet can change slightly from day to day, whether it’s due to swelling or simply wearing extra thick socks in the winter. Comfortable dress shoes for men sometimes have adjustable features—whether that’s laces, hook and loop straps, buckles, zippers or elastic inserts— that will help you accommodate these minor changes so you can stay at ease whenever you wear them.

7. Consider inserts, custom or otherwise.

Comfortable dress shoes for men don’t always come ready-made out of the gate. If you’ve found a shoe that has an otherwise perfect design and fit, but the sole doesn’t offer enough support, all is not lost! Insoles, orthotics, and shoe inserts can help provide extra cushioning and support in an existing pair of shoes. You can buy an orthotic insert that is designed to fit in any type of shoe or use custom orthotics to add support that’s exactly tailored to your individual feet.

We hope our guide has made shopping for comfortable men's dress shoes a little easier. Now that you know how dress shoes should fit and what features to look for, you can now find a pair to keep you looking sharp while feeling comfortable all day long


About the Author

Kaki Zell - Vice President of Sales, Marketing, eCommerce at Legs-4-Life LLC Kaki holds a Bachelor of Science degree in Business Administration and Management from Virginia Polytechnic Institute and State University. She’s been working in the medical device industry for over 11 years and currently serves on the Board of Directors for the Greensboro Science Center.  

Written August 2018 | Page last updated March 2022


Dr. Jeff Lamour. “What Does ‘Arch Support’ Really Mean?” 

MedlinePlus Medical Encyclopedia. “Plantar Fasciitis” 

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