I spent the entirety of my cousin Mark’s wedding reception standing against a wall like some awkward middle schooler at his first dance. Not because I didn’t know anyone—half the room was my family—but because the brand-new dress shoes I’d bought specifically for the occasion were basically instruments of medieval torture disguised as footwear. My big toes were screaming, my heels were raw, and I swear I felt a blister forming on top of another blister, which I didn’t even know was physically possible. When my mom asked why I wasn’t dancing, I lied and said I pulled a muscle at the gym. The truth was too embarrassing: I, supposed menswear expert, had prioritized looks over comfort, and was paying the price with every excruciating step.
Dress shoes shouldn’t hurt. It’s a simple statement that somehow remains revolutionary in men’s fashion. We’ve collectively accepted this bizarre idea that formal footwear must involve suffering, as if limping around like you’ve just completed some kind of corporate vision quest is an essential part of looking professional. I’ve witnessed grown men remove their dress shoes under conference tables, watched groomsmen switch to sneakers the minute ceremony photos were completed, and once saw a banker friend literally walk barefoot through Grand Central Terminal rather than take another step in his expensive torture devices.
Why do we do this to ourselves? Part of it comes from how most guys shop for dress shoes. We buy them, try them on for approximately 45 seconds in a store, take two steps on a carpet, and declare, “Feels fine!” Then we wear them for the first time to an all-day event where we’re on our feet for eight hours and wonder why we’re in agony. I’ve done this at least seven times in my life and apparently haven’t learned my lesson. My closet has a special section I call “The Museum of Bad Decisions”—beautiful dress shoes I wore exactly once before relegating them to permanent display status.
The good news? Comfortable dress shoes aren’t mythical creatures. They exist, I’ve found them, and I’ve spent enough time in foot pain to feel qualified to share what actually works. After fifteen years of trial and error (mostly error, if I’m being honest), I’ve developed a system for finding dress shoes that won’t make you want to amputate your own feet by lunchtime.
First thing’s first—most dress shoe discomfort comes from three main issues: improper size, insufficient break-in time, and badly designed lasts (the form shoes are built around). Let’s start with sizing, which isn’t as straightforward as you might think. Your dress shoe size is probably different from your sneaker size. I wear a 10.5 in most athletic shoes but a 10 in most dress shoes. And European sizing adds another layer of confusion—I’m anywhere from a 43 to a 44 depending on the brand, and sometimes even within the same brand.
The width is just as crucial as length. I spent years squeezing my slightly wide feet into regular width shoes, suffering unnecessarily because I didn’t want to admit I needed a wide size. There’s no shame in it—about 30% of men need a wide width, but most never try them. When I finally swallowed my pride and tried a wide size in Allen Edmonds, it was like the heavens opened up. Actually, more like my blood circulation returned. Same thing.
I met a third-generation cobbler in Chicago last year who told me something I’ll never forget: “Most men have never worn shoes that actually fit them properly.” Terrifying but probably true. He taught me the finger test—when trying on dress shoes, you should be able to fit your index finger between your heel and the back of the shoe. If you can’t, they’re too small; if you can fit more than a finger, they’re too big. This simple test has saved me thousands on shoes I would have regretted purchasing.
Break-in time matters enormously, but there are ways to expedite it without destroying your feet. The “wear them around the house” method works, but I’ve developed a more aggressive approach. For leather-soled shoes, I use a leather conditioner on the outsoles (not just the uppers), which softens them significantly. For the uppers, a combination of leather conditioner and careful stretching with shoe trees slightly larger than your normal size can work wonders over a week.
One time-tested trick I swear by involves a pair of thick socks, your troublesome dress shoes, and a hair dryer. Put on the socks, squeeze into the shoes, then use the hairdryer to heat the tight areas while flexing your feet. It looks ridiculous—my roommate once walked in while I was doing this and thought I was performing some kind of strange ritual—but it works. The heat makes the leather more pliable, and your feet shape it exactly where you need relief. Just don’t overheat the leather or you’ll damage it. Twenty seconds of medium heat is plenty.
Now let’s talk specific brands that have saved my professional life. Allen Edmonds remains the gold standard for comfortable American dress shoes, particularly their Park Avenue model, but only if you take advantage of their multiple width options. What makes them special is their cork insole that molds to your foot over time. The first twenty wears might be mildly uncomfortable, but after that, they become basically an extension of your foot. I’ve had my Walnut Strands for seven years now, resoled twice, and they’re more comfortable than most of my casual shoes.
For those seeking comfort right out of the box, British shoemaker Crockett & Jones makes dress shoes with what they call a “city sole”—a rubber-leather hybrid that provides more cushioning while maintaining a formal look. Their Sydney loafer saved me during a three-day conference in Vegas where I had to stand at a booth for eight hours daily. They aren’t cheap (around $675), but given that I’ve had them for five years of heavy use, the cost-per-wear is actually reasonable. Cheaper alternatives with similar comfort include Meermin’s rubber-soled options, which provide 80% of the comfort at about 40% of the price.
For something completely different, I’ve become a recent convert to Wolf & Shepherd, founded by a former track athlete who basically redesigned dress shoes from the ground up with comfort in mind. They look like traditional dress shoes but have athletic shoe technology inside. I was skeptical—they seemed too good to be true—until I wore their Closer Cap Toe through an entire wedding (ceremony, pictures, reception, after-party) without a single complaint from my normally vocal feet. While purists might scoff at the athletic shoe construction, no one can tell from the outside, and my feet certainly don’t care about tradition when they’re comfortable.
Spanish brand Carmina deserves mention for those with high insteps (like me). Most American and British dress shoes crush the tops of my feet, but Carmina’s lasts seem designed for feet with more volume. Their Detroit last specifically has saved me from the dreaded top-of-foot pain that many dress shoes inflict. The Forest last works beautifully too if you need more toe room without going to a full wide size.
The most radical comfort improvement I’ve found comes from custom insoles. I visited a podiatrist after one particularly painful wedding experience (my sister’s, where I was in the wedding party and couldn’t escape to a wall) and got fitted for proper inserts. They cost about $200 but completely transformed shoes I had previously relegated to my “Museum of Bad Decisions.” Just make sure you buy your shoes with enough volume to accommodate the insoles—you might need to go up half a size.
Let’s talk about the dress sneaker trend, which has been a godsend for many of us. While not appropriate for the most formal occasions, brands like To Boot New York and Koio have created sneakers with dress shoe aesthetics that work perfectly in business casual environments. I wore To Boot’s black leather dress sneakers to three consecutive investor meetings last month, and not one person noticed they weren’t traditional dress shoes. My feet, however, definitely noticed the difference.
One overlooked aspect of comfortable dress shoes is the socks you pair them with. Thin dress socks provide little cushioning and often slip down, creating uncomfortable bunching. I’ve switched almost exclusively to over-the-calf merino wool socks from American Trench or Boardroom Socks. They stay up all day, provide meaningful cushioning, and the natural fiber controls moisture better than synthetic alternatives. When I forgot to pack them for a business trip to Boston last fall, I actually went to a department store and bought new ones rather than wear the thin cotton alternatives I had brought.
What about breaking in truly stubborn shoes? Professional stretching services exist at most high-end cobblers and can work miracles. I brought in a pair of cordovan loafers that were borderline unwearable, and after a weekend on their stretching machines, they fit perfectly. Some shops even offer spot stretching for specific problem areas like bunions or wide toe boxes. The $40-50 service can save a $400 pair of shoes from becoming expensive shelf decorations.
For those on a tighter budget, don’t sleep on Johnston & Murphy’s comfort line. While not as refined as the higher-end brands, their XC4 system provides genuine comfort while maintaining a professional appearance. Their Hollis model has gotten me through multiple job interviews without distraction, which is really what comfortable dress shoes are about—allowing you to focus on the task at hand rather than counting the minutes until you can take your shoes off.
Finding dress shoes that don’t hurt isn’t impossible—it just requires more care and consideration than most men typically give to their footwear purchases. Take the time to get properly sized, understand your foot’s specific needs, break shoes in properly, and invest in quality where you can. Your feet spend an incredible amount of time supporting you; the least you can do is put them in shoes that don’t make them hate you. Trust me, your future self—the one who’s confidently networking at an event instead of leaning against a wall counting down the minutes until he can go home—will thank you.
