The 4 Most Comfortable Dress Shoes For Commuting to Work

The 4 Most Comfortable Dress Shoes For Commuting to Work
Have a new crop of hybrid dress sneaker companies finally solved the problem of needing a pair of comfortable shoes for commuting and a dressy pair for the office?

My first job out of college at a law firm came with a strict dress code: slacks and button-up every day, tie and jacket for client-facing events, and of course … dress shoes.

The problem was, I lived in New York City and my work commute involved over a mile of walking on concrete sidewalks and subway platforms. Dress shoes are fine on plush law firm carpets, but I quickly discovered wearing them all day was a recipe for serious foot and knee pain.

It’s a classic problem: you need/want to wear dress shoes for work but they aren’t comfortable enough for all day use, especially commuting by foot or bike.

So what’s the solution?

Don’t Accept The Dress-Shoes-Under-Your-Desk Workaround

My fix at the time was like a lot of people’s: stash two pairs of dress shoes under my desk – one black, one brown – and wear running shoes to work. It helped with the foot and knee pain but created another problem…

Wearing trainers with slacks looks terrible unless you’re Jerry Seinfeld, and even then it still looks bad but you don’t care because you’re a $950-millionaire.

Wearing traditional dress shoes to work can also create issues if your commute involves exercise. This post was inspired by a message from reader Joe Furstenberg, who bikes to work every day and reached out wondering: is there a shoe that can stand up to the rigors of a bike commute … and look good around the office?

Even a few years ago, the answer was “no.” There were slightly more comfortable dress shoes and slightly more dressy sneakers but the market hadn’t really addressed this need. Guys have been waiting for their “Looks Like A Pump, Feels Like A Sneaker” solution for decades.

Luckily, that’s changing. There are startups dedicated to making dress shoes that are both stylish and all-day comfortable and major brands have taken note, too.

So we’ve rounded up the most comfortable dress shoes on the market today.

The Top Comfortable Dress Shoes

Cole Haan ZeroGrand

Contrary to the old saying, can you have it both ways?

Cole Haan’s ZeroGrand wingtip oxford is a literal mashup: performance Grand.ØS sole mated to a leather dress shoe upper. On first blush, it seems too jarring to be something anyone would actually, like, wear. But consider your commitment to both social convention (the dress shoe half) and comfort (the sneaker sole) … do you really want both in spades?

It’ll garner a lot of comments and you can stand up from your desk and go run a marathon – in our book, that means it’s worth consideration. It's not for everyone, but the Grand line has been out since 2012 so people are used to seeing them by now. See how we styled them in Shane's Live Action Getup.

ECCO Men's Vitrus I Tie Oxford


It’s no surprise Ecco are on the list: they’re the tried and true entrant in the comfortable-but-not-dad-jeans dress shoe segment. For years, Ecco’s molded inlay sole, forefoot cork layer, and rubber soles have provided reliable comfort in a discreet package.

More recently, Ecco has also jumped on the dress sneaker trend with their “hybrid” offerings, but we don’t like that look as much as their traditional models. You be the judge.

Wolf and Shepherd Bannister Derby Shoe

Wolf & Shepherd

“Italian leather dress shoes made as comfortable as sneakers” is the claim, and Wolf & Shepherd’s line certainly looks the part. The company was founded by a former sneaker designer from Adidas and New Balance. And as crazy as this sounds, runner Juris Silenieks set a world record running a half marathon (with a 5:50 mile pace) while wearing a pair.

Under the hood (or is it under the laces?), a memory foam footbed and a high-density EVA foam sole act as shock absorbers, while a sheepskin liner and additional padding make this a compelling option.

Noble Sole The Wingtip 2.0


Warning: Apparently no one told NobleSole that autoplay music on websites is annoying. That said, NobleSole has crafted a hybrid dress shoe/sneaker with a unique look: something in between oxfords and a pair of Chuck Taylors that uses rubber soles and a calfskin upper to make a shoe that’s all-day comfortable.

More casual than Ecco or Wolf & Shepherd, NobleSole is a great option for more creative smart casual office settings.

Do you have a comfortable dress shoe? Let the community know in the comments!

Stillman Brown is a writer and TV producer who has created prime time content for National Geographic, Discovery, Travel Channel and many others. His interests span science & the natural world, personal growth, and food. He lives in Tulsa, Oklahoma.


  • Reply April 24, 2019


    Great post!
    Do you know of any brands with minimalist shoes that look great?
    I have had a hard time finding stylish zero-drop shoes with a wide toe box.

    I have a pair of Lems Nine2Fives and a Vivobarefoot Porto boot. I’m looking for more options.

    • Reply April 24, 2019


      Carets are well reviewed (run $350 a pair), though never tried them myself as I leave my zero drop for my athletic shoes.

      • Reply April 26, 2019


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  • Reply April 24, 2019


    Just my opinion of course, but I think those zero Grand shoes are the square toe shoes of the current decade…a lot of people wear them, but they don’t look good on anyone. Certainly not with slacks, maybe ok-ish with chinos/jeans if you have a casual office, but at that point you could probably wear fashion sneakers too.

    • Reply April 24, 2019


      Unfortunately squared toe shoes are still the squared toe shoes of the current decade 😆

      • Reply April 24, 2019


        Sad but true, lol.

    • Reply April 24, 2019


      Perhaps they will be too much for some of the more conservative crowd and older folk but I own 4 pairs of the ZeroGrand in a variety of colors and have received more compliments on them than any other pair of shoes I’ve owned. Wore them to a wedding and the over 60 crowd really loved them. A lady pulled me over to her husband to check them out and they went online to buy them right there on his phone, weird but my wife and I laughed about it and thought that was cool. Trendy? Sure, but in a good way. I typically stay away from fashion trends and focus more on my general style that will outlast the latest fad but these I think will be around for a while, especially since workplaces are getting more and more casual and these unlike other trends are actually comfortable and functional.

      • Reply April 24, 2019


        Well, I won’t argue with you about your personal taste or that of the people complimenting you… each to his own.
        I think they certainly don’t solve the problem laid out in the beginning of this article though. No one in the strict dress code law firm will mistake the ZeroGrands for a dress shoe as they are very clearly casual. Of course, you can certainly choose to wear casual shoes with a suit. I’ve done it plenty of times, just not with zerogrands!

  • Reply April 24, 2019


    Try Flexi, Nexus, Nogales or Leonard series are good.

  • Reply April 24, 2019


    I would say Nunn-Bush shoes are pretty comfy, stylish, and CHEAP! They have a gel insole heel insole which is nice. They do where down quick – I usually get them to last a year and a half with regular use. But they’re so cheap I can buy another pair!

    • Reply April 24, 2019


      Apparently, I cannot type, spell, or put any sentences together. The coffee has NOT kicked in, but you get the point!

  • Reply April 24, 2019

    Brown Gill

    These are slightly more casual, but still go great with chinos and less expensive than most of the options above. Built well and have lasted through almost daily use for the last 6 months with no signs of wear and tear.

  • Reply April 25, 2019

    Carlos Contente

    I like the Fuel line by Florsheim and I have one pair in ‘Cognac’

  • Reply April 25, 2019


    I know there are lots of options but Timberland has several lines of 5 star comfortable dress shoes. Check out the Timberland: MEN’S FOLK GENTLEMAN OXFORD SHOES

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