Life is too short to wear uncomfortable shoes — yes, even if the comfy ones look like this. (Zappos, Amazon)(Amazon, Zappos)
There was a time in my life when I'd spend every morning post-commute commiserating with friends and coworkers about how much my beautiful, expensive shoes had destroyed my feet. "Oh, but they look so good," I'd say. "And they were on sale!" I wasn't alone, either. Back then, we were all wearing shoes that brutalized our toes, arches and heels, suffering for the sake of fashion.
These days, my shoe conversations are notably different. I'm over 40 now, and compliments on my footwear choices are fewer and farther between. And the first words out of my mouth are often, "They're so comfortable." What I usually leave out is that they also happen to be pretty freakin' ugly, at least compared with my younger self's standards. As much as I still love the look of a sleek stiletto or a strappy sandal, I shudder at the thought of actually squeezing my foot into one.
Looking at my Instagram feed, I was convinced that I was the only person stepping out of the house in questionable-looking sneakers and slides. Influencers and stylish friends always seem to be wearing the latest chic shoe du jour. But then, fellow shopping editor Saundra Latham revealed that she'd recently purchased a pair of Crocs. And they were, um, not cute. I was intrigued. How many others were secretly wearing ugly but feel-good footwear? I decided to ask, and it turns out there's a whole crew of us!
Are you part of the ugly shoes club? Don't be shy: Tell us your unsightly but oh-so-comfy faves, and we'll tell you ours.
Actor Jeff Bridges loves 'em, and I'm sure your dad will, too. Senior Beauty Editor Jennifer Romolini's husband learned about the magic of these slides during an interview with the A-lister, who was wearing them at the time after recovering from surgery. "Bridges is right: They are, in fact, the most comfortable, stabilizing shoes I've ever owned, like having your feet ensconced in a bouncy, nurturing plastic cloud," she raved.
Not only do these sandals offer pain-free wear, but the sleek, minimalist design allows me to pair them with tons of different looks. The polyester straps are super-soft against the skin and haven't dug in or given me blisters once, even on a 20,000-step sightseeing day. The sandals are fully adjustable and have a contoured footbed for added comfort. You'll find them — and plenty more options — on our list of the most comfortable sandals.
"Hokas seem to have divided the shoe-wearing public into two camps: Those who appreciate their marshmallow-like comfort, and those who think they look a little too much like said marshmallows. That's totally fine with me — leave me all the Hokas, 'cause I'm getting tired of paying full price. But I'd do it again to experience the blissful cushioning and propulsion with every step, whether I'm running errands (frequent) or actually running (rare). And while Hokas do come in some eye-catching colors, you can also get them in black and white, gray, muted blue and other less 'Ask me about my Hokas' hues." — Saundra Latham, Commerce Editor
"The truth is, I didn't think these were ugly — I actually thought they were kind of cute — until my husband flat-out told me otherwise. Anyway, I've been a fan of sturdy, sporty Tevas since the '90s. I had a couple of pairs of the originals that lasted over a decade each of river trips and rock scrambling before finally falling apart. When it was time for a new pair, I spotted the HydraTrek and jumped on the chance to upgrade (again, because I thought they were cute). They've got a contoured, slightly more cushioned sole than the OGs, which makes a real difference on long city walks when I travel. The tread is seriously impressive — I haven't found an algae-covered rock it couldn't handle. As you'd expect, they dry fast, the straps are soft right out of the box, and best of all, no blisters. I've worn them regularly for about two years, but their true worth was revealed on a recent trip to the Yucatán. They climbed Mayan pyramids, carried me over rocky shorelines and became my go-to after my 'cute' sandals left me limping with blisters." — Janelle Randazza, Commerce Editor
"Do I consider these seriously cushy slides ugly? No. Do others? According to the reviews, very much so. But I'll take ugly when these sandals do soooo many good things for my joints. From the hips on south, my body is ... well, crap. Two knee surgeries, one hip surgery, janky ankles, etc. And when I say these cushy little numbers help with all of it, I'm not exaggerating. They're made from ethylene vinyl acetate, a material known for its cushioning and durability, and they have helped with all my various aches and pains. I've had them for over two years and though they get dirty (because I literally wear them everywhere), if I gave them a good scrub, you wouldn't know they weren't brand new. The only thing I wouldn't do is wear them on a longer walk — I've done so and end up with a mild blister by the end of a couple of miles." — Kris Scott, Commerce Editor
"I have two pairs of these and they're hands-down my comfiest sneakers. While they look OK with leggings, I wouldn't wear them with anything but activewear. They slide on and feel like a sock, but have plenty of cushion and support for ultra-long walks. They've never given me a blister, either. And while the brand doesn't advertise it, I toss these in the washing machine all the time. Now, the biggest downside is that they're costly, but I have a secret: I purchased mine in some of the not-so-popular colors at T.J.Maxx for a quarter of the price. You can usually find select colors there or on sale elsewhere." — Ellie Conley, Initiatives Writer
"Buying shoes is tricky for me: wide foot, narrow heel, high arches, Morton's neuroma, plus an injured little piggie. Four hip surgeries and back issues don't help, either. These bouncy, supportive Vionics let me stomp around all day and dance all night. On Sunday alone, they carried me 18,000 steps limp-free. I bought these beasts in black a year and a half ago and have worn them nearly every day, no matter the outfit. (Feel free to judge.) My husband actually thinks they're cute, but I suspect that's because they keep my complaints at bay. The cream/tangerine and rose versions, though, now those are cute." — Libby Sentz, Contributing Writer & Editor
"Before this story, I didn't realize my husband thought I had a 'whole ugly shoe collection.' He would also like to nominate these adorable multi-purpose slip-ons. Here's the genius: they're part shoe, part slipper. They tackle the age-old camping dilemma: You need something sturdy for walking around, but you also need something you can slip on half-asleep for that inevitable 2 a.m. bathroom run. And no, flip-flops are not an option — not with those nasty camp bathrooms. The quilted upper is made of 'adventure-ready ripstop,' which sounds intense but mostly just means it can handle a trail and a Target run." — Janelle Randazza, Commerce Editor
"I put off wearing Crocs for a long time. People I know praise their comfort, but I just could not bring myself to wear such an unattractive shoe. And then, something in me just ... changed. Why continue to subject my feet to shoes that pinch, rub and squeeze? Why not embrace rubber clogs that make my feet feel good? So, I spent $300 on Crocs in one fell swoop and I haven't looked back since. These floral cutout mules are currently my fave — I wear them pretty much every day around the house, to the grocery store, on walks with my dog. And guess what? I've gotten compliments on them. Okay, more like one compliment ... from a toddler who was also wearing Crocs." — Jeanine Edwards, Director, Commerce Initiatives
"I should preface this by saying I don't think these shoes are all that terrible looking, but they are a hybrid fisherman sandal and clog, which are both inherently 'ugly' shoes. Maybe 'fashionably ugly' is a better description? At any rate, they are one of my go-to pairs for spring and summer, and I wear them with everything, but I especially like them with cropped jeans, all the better to show off their chunky weave and aggressive silver buckle. I'll admit that it took close to a dozen wears to break them in, but now they're extremely comfortable, and the footbed is very supportive." — Jessica Dodell-Feder, Senior Home & Garden Editor
"Rain boots aren't known for being especially attractive to begin with, but mine are especially polarizing. (I mean, the phrase 'duck boot' alone is unsexy.) For starters, they don't hit right below my knee like a pair of societally acceptable Hunters; rather, they come up just past my ankles. This is because I've reached an age at which it's more important for me to have a full range of motion than it is to look slightly stylish but walk like the Tin Man (pre-oiling, mind you). They also have these funny curly-Q laces, which are objectively un-chic but allow me to tighten the foot opening without worrying about tripping into a puddle, since they can't come untied. In all honesty, I wouldn't wear them if I thought they looked that bad; in fact, when I pair them with a short skirt and black tights, I think they're quite cute. Cute, not sophisticated — but they're hands-down the most comfy water-resistant shoes my feet have ever donned, and with solid traction to, well, boot." — Britt Ross, Senior Deals Writer
"Before I went over to the dark side with Crocs, Birkenstock Arizonas were my go-to ugly, yet supremely comfy shoe. Summer footwear has always been a challenge for me, because in addition to having nonexistent arches, my feet are two different sizes. Between thin straps and sweaty feet, most sandals do a number on my dogs. But not my beloved Birks. The soft-footbed slides feel comfortable right out of the box, and I can wear them to walk for hours without pain. They're my go-to vacation shoe; I rarely travel without them. I've walked miles in Spain, Italy, Portugal and Montreal with them and they've never let me down." — Jeanine Edwards, Director, Commerce Initiatives
"I love these little booties, and I don't care who knows it. I have a curiously discontinued multi-color version that looks like little garden gnomes on my feet — and they inspire the same kind of magical joy. They’re the footwear equivalent of wrapping yourself in a blanket with a mug of hot cocoa — and that's not hyperbole. They're fleece-lined, so they actually do feel like a cozy blanket for your feet. I wear them on chilly morning dog walks and feel like I'm padding around in a cloud. Their water-resistant exterior and their grippy soles make them an MVP on dreary days. Are they sexy? Definitely not. Do I care? Not even a little." — Janelle Randazza, Commerce Editor
