What makes the ideal shoe? There isn’t a singular pair. But there are criteria, the most important of which is comfort. After all, dad shoes are more than just fashionable footwear. They’re chariots that help you shuttle your kids from the living room to potty in the nick of time. They’re shock systems for Baby Bjorns and piggyback rides. They’re catapults, capable of turning a mild-mannered father into a super dad when extraordinary reflexes mandate a sprint from one end of the kitchen to the falling juice cup at the other. In short, finding the most comfortable shoes for men makes a big difference.
Because it’s hard to determine comfort when you’re shopping online, we asked 11 men to tell us the most comfortable shoe they’ve ever bought. Some recommended classics (converse; pumas). Others, with more than a few qualifiers, recommended pure-comfort footwear like Crocs, Tom’s Shoes, and, yes, those dad-classics, Tevas. Still others recommended yard shoes and golf shoes that keep their feet warm and comfortable all day when they’re doing what they love. All of them come branded as the most comfortable shoes they’ve ever worn. Here are their selections.
These have been my jam ever since college. I think I’ve been through about four or five pairs since then. I love them because they slip right on. I love the suede look, too. I know it’s kind of 70s — at least that’s what I’m told — but I feel like I’m the only one I ever see wearing it, and I’m cool with that. Eventually there will come a day when my sons and I wear matching pairs. They’re a little young now, but I’m hoping their feet grow quick when they hit puberty - Neil, 38, California
So, I’ll be the first to admit that I ragged on Crocs all the time when they first became popular. I thought they were chunky-looking, ugly, and just really obnoxious. Then I tried them on. I don’t know what it is, specifically, but they’re game changers. They’re cushy enough to be comfy, but firm enough that my back, which has always been an issue, feels supported and that my posture is good. They’re so easy to clean, too. Working in the yard, and then spraying them off with a hose for ten seconds almost feels like cheating. The kids love them, too. Everyone in our family has a pair. - Jay, 43, New York
I remember seeing all the popular kids wearing these in high school. I was always in flip-flops, but when I got my first job in New York after college, I realized I’d have to do a lot of walking. So, I got a pair and fell in love at first step. The look is just iconic, but they’re really - in my opinion - some of the best walking shoes out there. They’re sporty-looking, but they’re also classic enough to go with a jacket and tie. Our dog chewed up a pair that I’d had for almost 12 years, and I was legitimately heartbroken. But, I got a new pair, and it was like falling in love all over again. - R.J., 37, New York.
My friend has a pair, and I always used to give him shit because I thought they looked like wontons with all the folds. I couldn’t believe it when my wife got me a pair. She thinks they look nice, and begged me to try them on. I have to admit, they’re pretty damn comfortable. First, I love not having to worry about laces. It might sound silly, but tying my shoes has always been a pet peeve. And I didn’t realize that they’re made from Earth-friendly materials. They may not be my favorite looking shoes, but they fit great and they’re environmentally conscious, which are big wins. Seth, 34 Ohio.
Classic dad-wear, right? The Tevas? The ones I have are called Hurricanes, and I love them. It might seem like an excessive amount of straps for a shoe, but I’ve always had a problem with sandals falling off — especially if I’m trying to be even the least bit active. These don’t do that. They stay put, and they’re very comfortable. I can play with the kids or the grandkids, or run errands, and then just kick them off when I walk in the door. I was skeptical at firsts, but now I see why dads like them so much. - Tim, 45, Texas
My sister-in-law bought me these. I’d never even heard of them. But her boyfriend has a pair, and he loves them. The first thing I noticed about them was that they didn’t require breaking in. Like, they felt good and fit naturally the first time I put them on. That’s always been a problem for me with flip flops, especially the ones with the little thong between the toes. They’ve also been really durable. I can’t think of a pair of sandals I’ve had that have lasted as long, or stayed in as good of condition as these. - Mike, 37, Pennsylvania
I never thought I’d like wool shoes. In fact, I didn’t really even know wool shoes were a thing until my kids got me these a few Father’s Days ago. My feet are like rainforests. This is well-known in my house. They get so, so sweaty. So, wool shoes didn’t exactly sound like the greatest idea. But, they’re made from moisture-wicking material, which actually keeps my feet pretty cool and keeps them from itching. The kids weren’t too subtle when they mentioned that to me, by the way. They were like, Oh, yeah, Dad check this out. They have moisture-wicking material! Maybe that’ll help with your sweaty feet! Thanks, kids. - Will, 40, Indiana
I’ve worn Chuck Taylors for most of my life.I’ve got baby pictures in Chucks. Senior portraits. Even wore them at my wedding during the reception. My wife has never given me a hard time about them, but she convinced me to ‘upgrade’ to a more sophisticated looking pair. They’re just as comfortable as the originals, and a little more subtle in the design. So, it was a compromise I was willing to make. I still have my Chucks - five pairs, actually - but these feel good, they look good, and they’re a nice change of pace once in a while. - Jimmy, 39, Massachusetts.
I’m a landscaper, so I need to take good care of my feet. These shoes are comfortable and durable, so much that I wear them on the weekends when I’m doing yard work at home. They cost more than I ever thought I’d spend on a shoe, but they’ve lasted me for quite a while. In fact, there have been times when I’ve dropped stuff on them, or gotten them snagged in bushes, and I was sure I’d look down and see them ruined. But, so far, so good. They don’t feel like walking on a cloud or anything, but for heavy-duty, yard work shoes, they’re the most comfortable I’ve ever worn. - Dave, 42, New Jersey.
I love golfing. And especially now, with the pandemic, it’s one thing my friends and I can do while maintaining social distance. So, I splurged and bought myself these golf shoes. To answer your question, no, they haven’t helped my game. But, I find myself being able to walk more comfortably around the course than I did before. My feet feel good, but my back and neck feel so much better with these shoes after a round. Even though I haven’t had them long, they’re definitely the most comfortable golf shoes I’ve ever owned. - John, 45, Ohio
I work in an office, so I have to wear dress shoes. I hate dress shoes. Like, hate dress shoes. I feel like I’ve cracked a code with these shoes. They look like dress shoes, but they’re basically fancy leather slippers. At least, that’s how they feel. They’re so comfortable that I’ve even worn them on Casual Friday, when we’re allowed to wear sneakers, and I got them in two colors. I don’t think I own any other shoes in two colors. - Marc, 34, Maryland