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Top 5 Comfortable Dress Shoes for Men 2017

Updated on February 14, 2017
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Greenmind is a writer, parent, and nature freak. He has struggled with knee and heel pain since running a triathlon in 2010.

Comfortable, Stylish Dress Shoes for Men -- the Top 5

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 5 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.

Sore Feet 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 “orthotic” shoes meant for sore feet often look like you’re on the run from the old folk’s home. Sharp, stylish men’s shoes that are comfortable and help ease your foot pain are hard to find. This article will help you find the right comfortable shoes for you.

Cole Haan Caldwell Lace-Ups

Comfortable Stylish Men’s Shoes: Cole Haan

These Cole Haans are my favorite work/dress shoes. Cole Haan make high-quality shoes that look really good. They are also 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. During the time I suffered from heel pain, these shoes almost never aggravated my condition.


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.

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. If you need dress shoes and your feet ache at the end of the day, shoes like these can make a difference.

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 afterwards. Then I ran a few miles on hills, and within a week or two I was wreck. 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 my Cole Haans, these 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 that I can stand and walk in from 7AM to 7PM 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.

Recent Data on Foot Pain

According to recent studies, foot pain is an increasingly serious issue among adults, especially older adults. 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! Over the years I have found several brands that work for me to help the pain in my feet. These shoes are also stylish and I often get compliments on them. This article will discuss several brands that receive high marks for being both stylish and good for alleviating foot pain.

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

I just started wearing these shoes, and though I have to admit they're not as stylish as they could be, so far the comfort level is very good. Dunham Men's Burlington Waterproof Oxford shoes are affordable and well-built, and I can stay in them all day without feeling like my 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 casual day or with a pair of dark corduroys and a crisp white button-down.

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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    • Ashish Dadgaa profile image

      Ashish Dadgaa 2 months 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.

    • greenmind profile image

      greenmind 2 months ago

      @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

      Ashish Dadgaa 2 months 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 :)

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