In our opinion, there is no such thing as too much comfy-shoe content. Sneakers, of course, can make for both comfortable and nice-looking footwear, but things get a little trickier from there as there’s a fine line between fugly and just plain ugly. So to find the best comfy and not-offensive-looking shoes out there,, we asked some cool women who spend most of the day on their feet — including servers, chefs, nurses, flight attendants, hairstylists, protesters, photographers, real-estate agents, and cleaners — about the shoes they wear. Their answers range from Shark Tank–approved high heels to classic Crocs to ’90s-style mary janes. Plus a few hacks for making your cute but ill-fitting shoes more bearable.
Best comfortable heels
“I’m telling you, anything, literally anything from Clarks that I’ve put on my feet, I’m like, Oh, yeah. I’m willing to pay more for them because I know that they’ll be comfortable,” says Cassadi Currier, a hairstylist at Pembly Joon. (She’s not alone: They’re an overwhelming favorite among our experts — three recommend the brand.) And according to Currier, these heels (not wedges) are her go-tos because they keep her feet comfortable for about four to six hours. Currier appreciates Clarks because they come in a variety of styles, including these “relatively cute” ones, rather than the “kind-of-grandma heels” or wedges. The Kaylins are a particular favorite because they “look like booties, but they have a sandal for your toes to show through,” she explains.
According to flight attendant Crystal Roseberry, women in her field “typically wear two pairs of shoes at work.” There are terminal shoes, which tend to be sexy heels worn from the time flight attendants arrive at the airport until they’re in the air, and there are in-flight shoes, which tend to be frumpy but comfy. But Roseberry says these mary janes from Clarks — of which she has multiple pairs — are “the best of both worlds — comfortable enough to wear all day long and still fairly cute.” They’re her “hands-down favorite,” she says. Sandra Hinton, who has been a flight attendant for 42 years, says these shoes are extremely comfortable thanks to the “rounded toe, cushion, and some support in your instep” as well as “a little bit of platform and a low heel.”
“I find the pickings to be kind of slim when looking for something supportive that still looks young and cool,” says server Tess Parker. Dansko’s Ankle-Strap Clogs, which Parker calls “a solid-gold tip” for anyone with knee or back problems, are the first pair of shoes she has found that fulfilled her requirements of being both supportive and cool-looking. The clogs have a “slight but forgiving platform” that helps make them so comfortable, according to Parker, who adds, “Our jobs tend to destroy shoes, but these are really long-lasting.”