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
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 & 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.
NobleSole
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.
