Here’s the 411: Another ‘90s shoe trend is back, so make room in your new collection of chunky clogs and “Meg Ryan”-inspired loafers for a new pair. Enter, the Mary Jane, a shoe popularized by the fictional Cher Horowitz and the real-life Sarah Jessica Parker, among many, many others. The Mary Jane is a classic shoe that debuted as a closed-toe flat with a buckled-strap across the top of the foot. Picture a baby doll’s shoe (which, is another name for the trend, BTW) and you’ve got the right idea.

While Mary Janes originated as a simple buckled flat, they’ve long since grown up with newfound details such as chunky doles, double straps, and beautiful textiles—sometimes even a combination of all three. That’s why the low-profile shoes are being paired with everything from dresses and skirts to trousers and denim: They’re universal. But like most other trendy shoes, their fit and comfort levels are not.

The best Mary Janes, at a glance:

• Duckfeet Lolland Mary Jane ($208)
• Dr. Martens 8065 Smooth Leather Mary Jane Shoes ($130)
• Sam Edelman Michaela Mary Jane Flat ($130)
• Rothy’s The Square Mary Jane ($159)
• Naturalizer Gen N Spark Mary Jane Pump ($150)
• Dansko Beatrice Mary Janes ($140)
• Cole Haan Bridge Mary Jane Ballet ($150)
• Circus by Sam Edelman Kay Mary Jane Heel ($90)
• Asos Design Sebi Chunky Mary Jane Heeled Shoes ($46)
• Clarks Emslie Lulin Pump ($70)

To ensure you add a pair of supportive pair MJs in your closet this fall, nationally-renowned podiatrist Jacqueline Sutera, DPM, who is a Vionic Innovation Member, says to look for Mary Janes with cushion and arch support—or, at the very least, enough room to accommodate a padded insole. “Avoid styles that feel tight, narrow, or stiff,” she says. With this in mind, she recommends steering clear of pointed Mary Janes and instead opting for styles with a roomy round toe box that matches the natural shape of your forefoot.

Sutera says to also pay attention to the heel, noting that a low to moderate heel height (around 2.5 inches) is best if all-day comfort is the goal. “Mary Janes with adjustable straps and rubber soles tend to be the most comfortable,” she adds.

Lastly, she says to look for Mary Janes with a flexible forefoot. “The shoe should bend at the forefoot to allow your foot to move normally while you walk,” she says. “Platform styles or Mary Janes with rigid soles that don’t bend and flex throughout the gait cycle will block and limit the normal range of motion. These usually end up being uncomfortable after walking in them for a bit.”

Dr. Martens, 8065 Smooth Leather Mary Jane Shoes — $130.00

Available sizes: 5-11

Sold in black and white, the Dr. Marten’s 8065 Smooth Leather Mary Jane Shoes are a timeless style worn on the runway and sidewalk alike. They’re moody, retro (given they’re a style from the ‘80s that’s been refurbished), and 100 percent on-trend. Like all Docs, they have to be worn in to soften the leather and mold to your feet. But once they’re broken in, they’re about as comfortable as it gets.

Duckfeet, Lolland Mary Janes — $208.00

Available sizes: 5-12, in European sizes.

Sold in nine gorgeous colors, the Duckfeet Lolland Mary Janes are like Doc Martens in that they’re reimagined schoolyard classics that have been around for decades. While these shoes aren’t the greatest from an insole stance—given there’s no built-in arch support—they’re designed to be roomy and wide, so they can accommodate custom and store-bought inserts for tailorable comfort. Bonus: they’re crafted entirely from eco-conscious materials, like natural rubber and Terracare leather, which is made using less resources than traditional leather.

Sam Edelman, Michaela Mary Jane Flat — $130.00

Available sizes: 5-11, in half sizes.

Here we have a classic baby-doll shoe in a bunch of fun colors and textures—all of which feature a padded leather insole for your tired tootsies. The tapered square toe gives the illusion of a point while maintaining the comfort of that roomy toe box Dr. Sutera suggests. As classic as the black patent option is, we can’t take our eyes off the luxe velvet colors which are perfect for the chilly winter temps, especially the warm Canyon Orange velvet and steely Smokey Blue.

Rothy's, The Square Mary Jane — $159.00

Available sizes: 5-13, in half sizes.

For a more casual silhouette, Rothy’s knit style is a great option. Instead of a buckle, these flexible ‘Janes (which are sold in four colors) are designed with a stretch strap that maintains its shape even after being pulled on and off feet. Beyond their comfortable flexible silhouette, they’re made with a padded insole so you can wear them for hours without winding up with aches and pains. Even better, they’re machine-washable.

Naturalizer, Gen N Spark Mary Jane Pump — $150.00

Available sizes: 4-12, in half sizes.

While the Naturalizer Mary Jane Pumps have a higher heel (3.25 inches) than Sutera normally suggests, their malleable “All-Ways Flex” forefoot platform aims to reduce the height difference, making them a comfortable, stylish option. Especially if you have a more formal occasion, like a holiday party or in-person meeting (do we still do those?) these will look chic without killing your feet. Now the only question is, will you choose black leather or tan suede?

Dansko, Beatrice Mary Janes — $140.00

Available sizes: 6-12, in European sizes.

The Dansko Beatrice Mary Janes—which are sold in black and red leather—look like something you’d see in every direction at your local farmer’s market. They’re casual, comfortable, and cute as can be, in that granola-y way that’s oh-so-very-in for Fall 2022. And it’s not just their looks, but their feel that stands out, too. They’re built with an EVA footbed infused with memory foam for cushioning and support, so you’ll be glad to wear them to your own farmer’s market, even when the line for butternut squash is wrapped around the corner.

Cole Haan, Bridge Mary Jane Ballet — $150.00

Available sizes: 7-11, in half sizes.

Love the look of a classic Mary Jane but prefer a tapered, square toe over one that’s rounded? The Cole Haan Bridge Mary Jane Ballet is the timeless black patent leather silhouette you’re dreaming of. Like the Same Edelman MJs, they have a semi-pointed design that’s surprisingly spacious. Oh, and did we mention that they’re made with foamy arch support? Comfy! Choose from simple black, gold lizard, or fierce leopard print.

Circus by Sam Edelman, Kay Mary Jane Heel — $90.00

Available sizes: 6-10, in half sizes.

Ready to take your Mary Janes out for a night out on the town? Check out the Circus by Sam Edelman Kay Mary Jane Heel, which is sold in six colors. The vintage-inspired platform heel and forefoot make them way easier to wear all night then your normal pumps or even kitten heels. That said, if you find that heels of all kinds make your forefoot fret at some point throughout the night, do yourself a favor and outfit your MJs with some extra padding, like Dr. Scholl’s Ball of Foot Cushions ($7)—they’re absolute game-changers

Asos Design, Sebi Chunky Mary Jane Heeled Shoes — $46.00

Available sizes: 4-11

If you’re on the hunt for pair of timeless-looking Mary Janes that doesn’t drain your bank account, give these a whirl. Their round-toe, black patent uppers look absolutely classic with skirts, trousers, and dresses, while the low block heel and 1-inch forefoot platform give you just a smidge of height. Since both platforms are sturdy and wide, they maintain optimal comfort while they’re on. Oh yeah—and they’re only $46.

Clarks, Emslie Lulin pump — $70.00

Available sizes: 5-12, in half sizes and three widths.

Similarly, this pair from Clarks is relatively affordable and lives up to the brand’s reputation of being durable and foot-friendly. The entire interior of the shoe is padded to prevent blisters on the heel and toes, and the footbed is outfitted with a OrthoLite insole that’s cushioned and breathable, so you can feel stellar while you stroll. The slight detailing draws the eye to give it some ‘oomph, too, a classy touch to an otherwise minimalist look.

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