Comfortable Dress Shoes for Men, 2019 Edition

Updated on November 5, 2018
greenmind profile image

I am a teacher, parent, and fitness writer. I have struggled with knee and heel pain since running a triathlon in 2010.

Comfortable Dress Shoes for Men

Men’s dress shoes that are comfortable enough to wear all day can be hard to find. If you’re style-conscious, the list gets even shorter. I’m a teacher, and I’m often on my feet all day – and I also want to look good. This article brings together my personal experience in shopping for dress shoes, along with select pairs from sites that rank shoes based on comfort and foot health. If you, like me, have a history of foot and heel pain, particularly plantar fasciitis, then this article is for you. These are the top five shoes that have a high consensus approval rating among wearers. I have chosen specific shoes to feature here based on comfort and, just as important, stylishness.

Comfortable Stylish Men’s Shoes, Top Choice: Cole Haan Lace Ups

These Cole Haans are my favorite work/dress shoes. Cole Haan makes high-quality shoes that are both handsome, and among the most comfortable shoes, I have ever owned. I am currently wearing a pair of dark brown cap-toe derby Cole Haan Caldwell lace-up shoes that I have just about worn out after over a year of walking up to 5 miles a day to and from trains and buses. I'm a teacher, so after all that walking I still need to be on my feet most of the day. This pair is a life-saver.

These shoes also helped a lot when I was in the midst of my first bout of a chronic foot condition called plantar fasciitis. This nagging, painful condition of the heel had me barely able to walk. It took months to resolve, and even now that I'm "healed" I still get familiar twinges of pain when my foot meets the pavement. During the time I suffered from heel pain, these shoes almost never aggravated my condition. They're comfortable, stylish shoes, just right for work.


Foot Pain and Dress Shoes

Those of us with sore feet and a desire to look good can find it hard to shop for shoes, since good-looking ones can leave us barely able to walk, and "therapeutic" shoes make us look like we're on the run from the old folk’s home. I put together this guide to stylish-yet-comfortable shoes for men like me who have a few aches and pains in heels, arches, and ankles, but still want to look like we care about our appearance. All of the pairs here have high ratings for comfort and foot supports, and are also good-looking and, in some cases, truly fashion-forward.

Fashion is the armor to survive the reality of everyday life.

— Bill Cunningham

ECCO Helsinki Cap-Toe Oxford Dress Shoe

This is my kind of shoe, with a clean, classic style. It gets top marks for foot comfort, and on top of everything else, it’s affordable. A really good choice and a top-rated product. The Helsinki Ecco Cap-Toe Oxford is imported and leather, of course, with moisture-absorbent lining and a removable leather-covered insole. One feature that helps give this shoe its top-ranked foot support and comfort is the direct-injected one-component polyurethane outsole.

I worked through a long bout plantar fasciitis, discussed below, with the help of comfortable dress shoes like these. If you need dress shoes and your feet ache at the end of the day, shoes like these can make a difference.

A Word About Style…

The shoes here are for dress or semi-formal occasions, basically office work shoes. My other Hubs feature running and walking shoes that are highly rated for foot and knee comfort. I have also included my own personal experience with foot-friendly dress shoes, with an eye on both comfort and looking sharp and stylish.

Be aware that not all comfortable men’s dress shoes qualify as “stylish,” so this article excludes some good candidates simply because they don’t meet my standards of acceptable men’s fashion. Maybe my standards are higher than yours, but in any case, a pair of shoes has to earn the approval of my internal “fashion police” before I’ll list it here.

For older men, in which group yours truly happily includes himself, comfortable shoes that look stylish are often less of an option and more of a necessity. We're caught between needing to look our age with classy footwear and needing to find shoes that feel good on aging heels and arches.

Do You Have Plantar Fasciitis? This Video Explains the Condition

My Fight with Plantar Fasciitis

As I have written about extensively elsewhere on this site, I was hit with plantar fasciitis shortly after running a triathlon. I trained for months on flat ground, and the race was on flat ground, and I was fine afterward. Then I ran a few miles on hills, and within a week or two I was a wreck. Never had I encountered such a nagging, seemingly endless condition. It hurt to walk, let alone run. A visit to my GP gave me a diagnosis -- she told me I had plantar fasciitis and the way she said it I knew that it was more than just a little temporary ache in my feet.

Foot Pain Doesn't Mean Giving Up on Style


With plantar fasciitis, once your fascia is inflamed, and in pain, every step impacts the injury and makes it worse.

What Exactly Is Plantar Fasciitis?

Plantar fasciitis is chronic inflammation of the plantar fascia, which is a broad band of connective tissue that runs underneath your heel. The heel bone has a relatively sharp spur at the bottom, which with too much-repeated impact can damage and inflame the plantar fascia. Once your fascia is inflamed, and in pain, every step impacts the injury and makes it worse. In severe cases, you have no choice but to stay off your feet until it heels, and that can take a long time. I had pain to some degree for almost three months, until I found a pair of running shoes that essentially cured me – Nike Air Max runners with a proprietary heel impact unit.

Florsheim Men's Heights Moc Toe Oxford

After Cole Haan, Florsheims are my go-to work shoes. I'm a high school teacher, and I'm on my feet for most of the day, but at the same time I need to look good -- no runners or non-leather shoes for me, thanks. Florsheim makes some really handsome shoes, but it wasn't until I found this pair that I realized they had some of the most comfortable shoes as well.

Florsheim Men's Heights Moc Toe Oxfords are sharp and stylish shoes with a classic line that I like to pair with my more formal looks -- gray wool trousers, pale pastel shirt, slim charcoal jacket, for example. Florsheim shoes possess that rare combination of wearability and style that this guide is all about. More proof that people like us with foot pain don't have to give up on looking good. With Florsheims I can stand and walk in from 7 am to 7 pm and not end the day in agony. Even when I was suffering with the pain of plantar fasciitis, I was able to wear my Florsheims day in and day out. A great shoe and a real life-saver for me.

Fashion is about dressing according to what's fashionable. Style is more about being yourself.

— Oscar de la Renta

Shoes and Serious Foot Conditions

If you have serious foot ailments, such as osteoarthritis and rheumatoid arthritis, then you may be interested in recent research that points to the role of shoes in helping you find comfort. According to the journal Current Opinion in Rheumatology, “Emerging research suggests that there may be a significant role for foot orthotics and footwear in the treatment of rheumatoid arthritis and osteoarthritis of the hip, knee, and foot.” Surprisingly, the role of shoes and footwear has been somewhat neglected by researchers studying foot, knee, and hip conditions. Although there is good preliminary evidence that footwear can affect the progression of arthritis and other serious conditions, few studies exist that address this question directly.

Dunham Men's Burlington Waterproof Oxford

Dunham Men's Burlington Waterproof Oxford

Dunham Men's Burlington Waterproof Oxford shoes are affordable and well-built, and you can stay in them all day without feeling like your feet are about to fall off. It's true that they're not as sleek as some of the other shoes here, but they look good, especially on a casual day or with a pair of dark corduroys and a crisp white button-down.

These shoes are a solid choice for people who work outside or encounter wet weather in the course of a normal day. And that's truly important because according to recent studies, approximately 24% of adults have foot pain and related physical conditions. Much of this has to do with the type and quality of footwear that’s available to people with foot pain, and men, in particular, have relatively few options. It’s truly challenging to find good-looking men’s shoes that are comfortable and won’t make foot pain worse. I know – I have to be on my feet most of the day, and I also have to look presentable. Athletic shoes are not an option!

Here's to Happy Feet!


Riskowski, Dufour, and Hannan: "Arthritis, Foot Pain & Shoe Wear: Current Musculoskeletal Research on Feet," Curr Opin Rheumatol. 2011 Mar; 23(2): 148–155.

Hill, Gill, Menz and Taylor: "Prevalence and correlates of foot pain in a population-based study: the North West Adelaide health study."


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    • profile image

      Harry Millward 

      5 months ago

      Brillz site its what iv been looking for most other sites seem to be for american that ok but i prefer british

    • Ashish Dadgaa profile image


      2 years ago


      Ohh wow, that's very easy.

      I will try this instead of old fashioned Amazon capsules.

      How many products links we can add in one hub?

      Thank you so much for your help :)

    • greenmind profile imageAUTHOR

      GreenMind Guides 

      2 years ago from USA

      @Ashish -- thanks I'm glad you like it.

      You can easily add Amazon links in text by highlighting the anchor text and choosing the "link" icon (the little chain link icon in the capsule toolbar). Paste in the Amazon link to the product and the HubTool does the rest.

      Have fun!

    • Ashish Dadgaa profile image


      2 years ago


      Very nicely written hub.

      I loved all your suggestions for the shoes but my personal favorite is ECCO Men's Helsinki Cap-Toe Oxford Dress Shoe :)

      I must buy this for my office wear. Thank for the suggestions :)

      p.s. how did you add Amazon link in between your written description? This looks neat & decent compared to our traditional HubPages Amazon capsules.


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