What Are the Best Mary Janes?

“I don’t often go for colorful shoes, but I like that the two-tone is a bit more of a statement than your standard black or cream Mary Jane,” says Tessa Domzalski, the creator behind the YouTube channel ModernGurlz. “The square toe also makes it a bit less ‘sweet’ which is a better fit for me.” Domalski says that because her feet are a little wider, it took her some time to break in the shoes but that she can now stomp around in them with no problem. She also finds the heel incredibly comfortable.

Isabella Weatherby, founder of the British brand Peachy Den, says wearing mary janes “instills a sense of nostalgia to being back in the school classroom.” Her pair of choice comes from the independent British brand Home of Hai and are made of leather and velvet. Weatherby, who “inherited flat feet,” says she always prioritizes comfort in footwear. “My mary janes are the perfect intersection between timeless style and an orthopedic shoe,” she says.

Strategist senior editor Winnie Yang’s mary janes are from Caron Callahan. “The rounded square opening is flattering and elegant, the strap and profile are in just the right proportion to the sole, and they come in such rich, vibrant colors,” says Yang. “ I wear them everywhere and with everything: dresses, jeans, and, probably most of all, my collection of balloon and barrel pants.” Since her feet are wide, Yang went half a size up to make sure the shoes weren’t too narrow.

“I just can’t myself wear ballet flats; they don’t work for me. So mary janes are kind of like an elevated version of that,” says artist Taylor Quitara. As a self-confessed maximalist, she thought this chrome pair with buckle detailing would be perfect — and hoped they would be comfortable. “They seriously are: I’ve walked seven miles in them before and been fine,” she says. Quitara styles her shoes for almost any kind of occasion, to the point where pictures of her outfits have been shared dozens of times on Pinterest: “I’ve had conversations with people and they’re like, ‘Oh, you’re the girl with the colored tights and silver shoes.’ I didn’t know what they were referring to until someone sent me the shoe inspo on Pinterest.”

“These remind me of the shoes on Bratz dolls — in your face and ideal for stomping around,” says Strategist writer Ambar Pardilla. Though they are chunky, these mary janes from Larroude are actually lightweight and remarkably comfortable, says Pardilla (who has been known to end up with a twisted ankle from shoes with only a wedge). “I feel balanced because of the platform,” she adds.

“I love these mary janes so much I actually have a tattoo of them,” says Vivian Chen, writer of the fashion newsletter The Molehill. “Seeing the robin’s-egg-blue interior lining against the black leather makes me happy — it’s a very Alice in Wonderland color scheme.” To style, Chen will pair these mary janes with socks, which, along with the dainty bow, make the style more doll-like.

Strategist writer Lauren Ro managed to get the iconic Carel three-straps on sale — she chose the lower-heel style as she wanted an everyday kind of shoe. But what surprised Ro about them is how comfortable they are. “As with all new shoes, there was a tiny bit of blistering, but after a couple of wears they broke right in,” she says. “I also have bunions, and though these shoes look narrow, they actually accommodate them just fine. I can wear these all day long.”

“You can’t go wrong with a pair of Repettos ever — the shoes are classic, unassuming, unfussy,” says Pardilla. “I couldn’t resist getting them in that Coca-Cola red. The shininess of the patent leather makes the color look so saturated — like putting a coat of gloss on red-lipstick-covered lips.” Pardilla sized up in the shoe (a 38 instead of her regular 37) and says, thanks to their snug T-strap and modest heel, they’re remarkably walkable.

Illustrator Poppy Almond’s pair of mary janes comes from Acne. “They’re the perfect balance of fun with the star details and cool with the chunkier gum soles,” she says. “They have this supersoft leather that makes them one of the comfiest and most reached-for shoes in my collection at the moment.”

“Mary janes were something I spent my childhood wearing; they always made me feel really girlie,” says stylist Briana Andalore, whose client list includes Julia Fox. Her current favorite pair is from a Repetto collaboration and has a perfectly chunky platform to give her shorter frame some height. “They make me feel really feminine and cute,” says Andalore. “Repetto has never stopped making mary janes and ballet flats and has always been of the highest quality and done the coolest collabs.”

Emilia Petrarca, freelance writer and founder of the newsletter Shop Rat, invested in these mary janes after spotting them on a Simone Rocha store manager. “I saw she posted a picture wearing these mary jane flats, and I think I had the most basic human instinct that I was just like, Oooh, shiny!” The shoes are made from a foil Petrarca says is bendy and moldable but not at all flimsy: “I don’t feel like I’m going to ruin the foil when I walk around. I wore them yesterday to run some errands; they’re definitely comfortable, and the strap helps them feel snug on my feet.”

Three of the people we chatted with told us about their Margiela Tabi mary janes, including presenter Jasmine Muller. “They combine the distinctive split-toe Tabi style, inspired by traditional Japanese socks, with the classic mary jane strap,” she says. Yotka has owned her pair since spotting them on Chopova Lowena’s Laura Lowena in London. “The mary jane has a girlish association — prep school, Sunday school, sweet 16s, etc. — but I really liked how Laura wore them in a more punk and sporty way, not so precious,” she says. Yotka advises anyone buying a pair of Tabis to go out and have a rubber sole added to them immediately or the leather sole will suffer. But Yotka found her pair comfortable right out of the box, sturdy, and recognizable. “I think it’s a nice version of a Tabi because it does seem like a shoe people recognize at first, even if they aren’t quite as hard-core fashion-obsessed,” she says.