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 cart your kids from the living room to potty in the nick of time. They’re shock-absorption 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. TLDR: finding the most comfortable shoes for men makes a big difference.
It’s hard to determine comfort when you’re shopping online. So, for that reason, 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 Tom’s Shoes, and, yes, those dad-classics, Tevas. Still others recommended specific yard shoes and golf shoes that keep their feet warm and comfortable all day when they’re doing what they love. All of this footwear come branded as the most comfortable shoes these men have ever worn. Here are their selections.
I wear these with everything except shorts — they're that comfortable. And because they're a boot, I can wear them on a date just as easily as I can to split wood. They're made in the U.S. too, which I like. - Phillip, 39, Michigan
I had these in high school. And then I went off to college and started wearing real shoes. Well, a couple of years ago I bought a pair of the 1460s and they're even better than I remembered. I'm on my feet a lot, and the rubber soles are really comfortable. The look is easy to wear, and they are very, very durable. Whenever I do wear them out, I'll definitely buy another pair. - Sam, 46, North Carolina
My wife got me these because she loved the company's flats for women. I was skeptical, but the RS01 was super comfortable right out of the box, and because they're woven, they're fully washable. For the first time in my life, I can wear white shoes without worrying about getting them stained. Just take out the insoles, throw them in with the towels, air-dry, and the next day I'm crispy AF. - Jon, 38, Tennessee
These were a gift because I grew up skateboarding and liked the look. They seemed like Vans' Sk8-His that I used to wear ripping around the neighborhood. But the more I've read about the company, the more I like them. Besides being super comfy and breezy, they're also super eco-friendly, which is cool, since eventually I'll wear them out and have to get rid of them. But so far, they're holding up really well. - Bjorn, 29, Indiana.
I hate dressing up. Totally hate it. But these shoes wear like a sneaker. They've got a soft bottom that's good all day, and the laces only cross twice over my high arches. Even better, because they're leather, they raise the profile on just about any outfit, from shorts to slacks, when sneakers or flip flops would get me a look. My wife is thrilled, and finally I'm actually comfortable. Win-win. - Tony, 26, Washington, D.C.
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 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
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 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’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 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