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The comeback kid over the last few seasons is undoubtedly a lovely ladylike-gone-cool-girl shoe named Mary Jane. What once was a conservative classic has returned in versions spanning viral trends like balletcore, quiet luxury, ladies who lunch, and even sporty hypebeast. From ballet flats to sneakers, loafers, platforms, and block heels, these shoes cater to every style inclination.
The shoe not only blends nostalgia with a modern flair, but it’s a comfortable and wearable trend—as long as you choose wisely. Every brand name has launched its take on the Mary Jane shoe. From Sandy Liang to Prada, Marc Jacobs, Dr. Martens, and Marni—as well as Sam Edelman and Steve Madden—you couldn’t hide from style even if you tried to. With that in mind, I’ve tested a plethora of styles and scoured the internet for reviews to ensure you have the most comfortable options available. So, whether you’re looking for a chic everyday shoe or a statement piece for a special occasion, the wide selection of Mary Janes ahead will never have you compromising comfort for style.
A stacked heel is always a more comfortable option than a stiletto or kitten heel. This heeled, square-toe version of a Mary Jane from Tony Bianco is made from soft, genuine leather and a rubber sole. In other words, you get a soft insole and grippy traction in the form of a ladylike dress shoe.
Colors: Black
Sizes: 5-10
Material: Leather
A summer version of your classic Mary Jane leather flats come in this two-tone espadrille version from J.Crew. These Spanish-made shoes feel like luxury comfort for under-$200. The jute stitching and espadrille platform adds a touch of seasonal jazz, while the overall style and silhouette reigns classic.
Colors: Black, Ivory
Sizes: 5-12
Material: Leather
Customer review: “These are the most comfortable shoes I’ve ever owned. They look so elegant, and you can wear them with casual jeans or you can dress them up with a little black dress. I love them. They fit true to size! I recommend them.”
A bold (and bright) take on the OG Weejuns by G.H. Bass might be one of the best juxtapositions to grace our shopping carts. The saturated color in durable leather—that softens and gets better with age—is rare. Weejuns are known for personalized comfort after a short break-in period. If the bright color isn’t your jam, be sure to scope the other retailers for alternate options.
Colors: Pink, Black, whiskey, wine
Sizes: 5-11
Material: Patent Croc Embossed Leather
Customer review: “I was so surprised to find that these are super comfortable. I love Weejuns, and I adore this style, but I expected I would need to return these for being too pinchy and narrow. They aren't at all. They're lovely and wonderfully dressy and classic, and COMFORTABLE!”
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Best Insole for Foot Health
Vivaia Pointed-toe Mary-Jane Flats
Vivaia’s “comfort heels” pretty much broke the internet through targeted ads (sorry, not sorry, if you haven’t seen them yet—you’re going to want to). This modern take on classic ballet flats features the same shock-absorbing midsole and contoured footbed that makes the brand’s heels so comfy. You get sneaker-like comfort and an anti-slip grip in a sophisticated style.
Colors: 12 options
Sizes: 5-11
Material: Antimicrobial knit
Customer review: “Love the shoes, they fit perfectly, look great, and are so light and comfortable.”
Even though they don’t seem like it at first glance, reviewers claim these to be “the most comfortable” shoes. As a huge fan of Bared Footwear, I support the claim. The shoes are designed with comfort at the top of mind. The secret sauce is the biomechanical footbed, providing cushioned comfort and efficient arch support to reduce heel pressure and provide support. Plus, the square-toe element of this design provides a roomy footbed, which is helpful for people who suffer from plantar fasciitis.
Colors: Black, navy, leopard, red, silver, white
Sizes: 34-43
Material: Leather
Customer review: “These are the most comfortable shoes I've ever worn. So much fun and so many compliments!”
Chunky rubber meets Marni’s soft leather in this shoe, which is a match made in heaven in the world of comfort and wearability. It’s the brand’s popular Pablo sneakers in Mary Jane form, and it’s just begging to get styled with a feminine frock and socks (or is that just me?!).
Colors: Black, White
Sizes: IT35-IT41
Material: Leather, rubber
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Over the last decade, Dolce Vita has emerged as a major on-trend brand of affordable, high-quality footwear. It’s the best place to go for relevant styles that won’t break the bank and won’t hurt your feet. This pair of square-toe metallic flats is just that.
Colors: Red, black, brown, gold, silver, ivory
Sizes: 6-11
Material: Leather
Customer review: “Absolutely love these flats. They're buttery soft, easy to close, and they don't look too school girly. The ivory goes with everything. They fit true to size. I am considering getting the snake print next as a fun neutral!”
Prada’s take on the Mary Jane is balletcore at its finest. The chocolate brown and gold hardware combo makes this seasonless and worthy of the designer's investment. Italian-made footwear from the highest-quality materials is as good as it gets.
Colors: Brow, Red
Sizes: 35-41
Material: Satin
Madewell Greta Ballet Flat
Now 20% Off
Madewell’s Greta flats are a bestselling style that continues to gain popularity and emerge into new versions, textures, and colors. It’s a simple, wear-with-anything shoe made from soft Italian leather and a new and improved cloud-like lining for superior comfort.
Colors: 11 options
Sizes: 5-12
Material: Leather
Customer review: “I hadn't intended on buying these shoes. But something about them reminded me of ballet classes I took as a kid? - stayed with me. Now I have them and yes, they're great. The cushioning inside was an unexpected plus - I don't ever remember my real ballet shoes ever being this comfortable.”
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Most Durable
Dr. Martens 8065 Virginia Leather Mary Jane Shoes
Anyone who owns a pair of Docs knows that the required break-in period is worth the wait. Luckily, with its take on the Mary Jane, the that time period is cut in half. You get the same foot-forming leather, durability, and tread as the brand’s bestselling boots but in a ladylike design. Check out the multiple retailers for a variety of colors.
Colors: Olive, Tan, Black, White
Sizes: 5-11
Material: Leather
Customer review: “The nostalgia of these shoes makes me feel youthful and free-spirited. I love them. The comfortability and quality are on point.”
Best Performance Fashion
Ganni Yellow Performance Velcro Mary Jane Ballerinas
Now 16% Off
The Vibram sole might have been partially included for the fashion irony of this design, but that doesn’t mean it’s not real. Vibram soles provide the best quality, durability, comfort, and traction for active outdoor footwear, and this pair of Ganni Mary Janes features all of that. Consider this gorp-y footwear a style that actually lives up to the hype.
Colors: Black
Sizes: 36-39
Material: Rubber, nylon
Open-weave Mary Janes acts like sandals with more support and without exposing your toes. So, if you’re a few weeks overdue on a pedicure, this is the shoe of summer to get away with. The woven leather provides breathability, while the leather basket weave gives a secure fit via soft leather.
Colors: 8 options
Sizes: 43-45
Material: Leather
Customer review: “So cute & so comfortable. I never review anything, so it's a testament to how much I love these.”
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With over 1,000 five-star reviews, these machine-washable ballet flats earned a spot on this list. What feel like slippers on your feet are actually sophisticated footwear you can wear out and about. They are soft and comfortable, with a cushioned insole and rubber outsole for outdoor traction.
Colors: 10 options
Sizes: 5-13
Material: Recycled knit
Customer review: “I got my first pair of Rothy’s and they have been all I needed to pack in order to match outfits on my recent trips to Morocco, the English countryside, and various metropolitan cities! So comfortable and I’ve done endless walking in them. I will definitely be buying more in other colors! People keep stopping me to ask me where I got them, that must be a great sign!”
HEREU makes footwear using leather so good you can smell it from blocks away. This modern take on the Mary Jane is both on trend and timeless (and on sale)!
Colors: Brown
Sizes: 35-41
Material: Patent Leather
The juxtaposition of skater girl style with a feminine detail is giving the sneaker of summer. If an all-white shoe isn’t for you, check out the various retailers for a ton of other colors like red, black, yellow, and blue.
Colors: Ballet Rose, White, Black, Red, Stripe
Sizes: 6-10
Material: Cotton canvas
Customer review: “I am so happy I grabbed a pair of the new Vans’ Mary Janes! I appreciate the much lighter and lower profile design over the lug sole. They have a non-textured, smooth rubber toe cap. They are so comfortable and super cute! I get compliments each time I have worn them! Great job, Vans!”
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If you’re a Clark Wallabees collector like me, this is a must-have pair to add to the arsenal. The Mary Jane detail dresses up the otherwise super casual moccasin-inspired desert shoe. For those who aren’t collectors, this is a great gateway into the world. The soft suede and rubber outsole is an entirely new world of comfort.
Colors: Maple
Sizes: 6-10
Material: Suede
Mules are the easiest shoes to wear thanks to their slip-on/slip-off method of dressing. This pair from AGL remains as functional as ever, with soft leather inner and outer and a curved footbed.
Colors: Red
Sizes: 35-41
Material: Leather
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