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The 25 Best and Most Comfortable Mary Jane Walking Shoes

The best Mary Jane walking shoes can be overwhelming to find! These shoes come in a variety of styles from day wear, formal occasions, or wherever there will always be a style of Mary Jane shoes to fit the occasion.

With a variety of styles, they have evolved with fashion. Just about every shoe brand has a spin on these timeless shoes.

If you have prior purchases of Mary Janes, you know how comfortable these shoes can be. They are perfect for long days of standing, walking, exercising, and more!

Here’s the scoop on the 25 best Mary Jane walking shoes!

Mary Jane Walking Shoe History

The Mary Jane style shoe has been around since the early 20th century.

The original Mary Jane shoe was called bar shoes. These shoes got their popular name from the Brown Shoe Company, which liked to name shoes after comic strip characters.

As a result, they named their bar shoe after the Buster Brown comic strip. The shoe was named after Buster Brown’s beloved Mary Jane. After the brown shoe company did this, Mary Janes took off.

Over the decades, they have stayed around. In the 1930s, this shoe was popular among little girls. A little girl named Shirley Temple always had on Mary Janes.

Many little girls wanted them so they could look like her. The style has evolved but has never faded away.

1. The Dwarves Handmade Leather Flat Mary Jane Shoes

These shoes are great for everyday wear, especially if you work in an office setting. However, they can also be dressed up!

These round-toed styled Mary Janes include a feminine strap with a gold accent to ensure a secure fit.

2. Lita Mary Jane Square Toe Pump

These Mary Janes are not your classic design as they have a retro 70s feel to them. They are great shoes if you are looking for comfortable walking shoes and a unique shoe to own.

3. Steve Madden Mingle Black Patent

Block heels are a more recent trend but one that will be around for a while! Not only are they stylish, but they are also easier to walk in.

They are also roomy Mary Janes with an adjustable strap so that you can tighten/loosen the shoe to your desire.

4. ASOS Maisie Chunky Mary Jane Flat Shoes

These chunky Mary Janes are a play on the classic Mary Jane style. They are platformed flat shoes, perfect if you have a flat foot.

The shoes are a wide fit. This means that if you want a relaxed fit, you should order your size. If you want more of a secure fit, size down for the best fit.

5. Free People Stella Mary Jane Platforms

The two-strap Mary Janes are perfect for a casual outfit. With an adjustable fit, these shoes are perfect to wear for a long time.

Its low heels and loop straps, make it a great pair of walking shoes to have for long work days or a more formal event.

6. Dr. Martens 8065 Smooth Leather Mary Jane Shoes

The retro Mary Jane’s are perfect if you are looking for a blast from the past. These became popular in the 80s and are now making their comeback.

The durable leather used by Dr. Martens is, of course, used on this shoe. They are made to last you for years with their Goodyear welted heat-sealed design.

These shoes come with free shipping if you get the standard ground shipping or the 5-7 business days shipping.

7. Duckfeet Lolland  

This classic style of Mary Janes comes in a variety of colors. These shoes are terracare leather upper as well as water-friendly.

With extra room at the top of the foot, it provides a looser comfort fit. The arch is more on the neutral side and has Italian Crepe Rubber on the outsole to provide more comfort.

8. Clarks Emily Pearl

These 2 ¼ heels are a popular shoe that is worn by flight attendants.

With memory foam to form to your foot shape, they are perfect for those long days of standing, especially when you are stuck standing on an airplane. There are many different heel heights among this brand, but they are all just as comfortable.

9. Miu Miu Denim Mary Jane pumps

While these shoes were inspired by streetwear, they are mixed with the comfortable classic Mary Jane style of shoe.

These shoes are for sure a staple piece and will not take the back seat to any event. They may be more on the expensive side, but if you can afford them, they are more than worth the price.

10. Nasty Gal Daisy Print Mary Jane Platform Heels

These heels are more on the fun and playful side of Mary Janes. The sky blue and white daisies are perfect for a picnic or a day in the park.

11. Birkenstock Tracy

These Mary Janes provide good stability for a long day. The adjustable strap provides great support for daily comfort.

The insole is made to form to your feet, just like any other Birkenstock. These shoes are extremely comfy and will last for years.

12. Pink Platform Mary Janes

While this shoe does appear to be higher, the platform on the front of the shoe helps for more of a small wedge feel.

13. Dansko Women’s Fawna Mary Jane

 These Dansko Mary Jane shoes are one of the best walking shoes. With the removable insole, they are perfect for long-distance.

They come in various colors to choose from and are perfect for all-day walking.

14. Jimmy Choo Baily 100

While these beautiful stiletto shoes do not seem like they would be comfortable, Jimmy Choo’s is known for the unique designs and the comfort that they offer. This pointed-toe Mary Jane style is perfect for a night out.

These are not in everyone’s price range, but if you can get your hands on a pair of these, they are well worth it.

15. PG Lite Alegria Women’s Paloma Leather Shoes

With a firm heel counter, a memory foam footbed, and a removable footbed, this shoe is great for lower limb support.

Additionally, they come in many different designs so there is something for everyone! These will quickly become your new favorite daily shoe.

16. OrthoFeet Springfield Stretch

If you are looking for a comfortable shoe to help you with issues like Achilles Tendon, Plantar Fasciitis, and lower back pain, then this is the pair of shoes for you.

The Orthofeet shoes are perfect for all types of feet! They have adjustable arch support so you can change it based on if you have a low arch or a high arch.

Additionally, this shoe adjusts based on the contours of your foot.

17. ABEO B.I.O. System Marisol Metatarsal

These Walking Co. Shoes are perfect to help you to relieve pressure and pain. They are great shoes for someone trying to find a more comfortable shoe.

18. Rothy’s The Square Mary Jane

Rothy’s Mary Janes are an eco-friendly spin on the shoes. Made from plastic bottles, the comfort these shoes will give you is unreal.

These shoes are on the tighter fitting end, but that does not make them any less comfortable.

19. Skechers Stretch Fit: Arch Fit Cleo Wedge

These sketchers are another pair that contours to your feet. They have an air-cooled memory foam insole and a knitted outsole, to allow airflow. These shoes are perfect if you live an active lifestyle.

20. Dansko Women’s Hilda Mary Jane

The all-day support of the Hilda Mary Janes is just the start of why you should consider buying these shoes.

The insole has arch technology that forms to your foot. They are a lightweight design that keeps the feet cool.

21. ECCO Women’s Biom Lite Mary Janes

If you are looking for a lightweight shoe, Ecco Biom Lite Mary Janes is a great option! They are designed to feel like you are barefoot, because of how the shoes adjust to your feet.

Sporty people especially love this shoe because it includes breathable mesh and all-day comfort along with adjustable straps.

22. Marc Jacobs The Plaid Mary Jane

This unique spin on a Mary Jane shoe holds a special place in our hearts. They have the vibe of Bratz doll shoes, with the chunky rubber sole shoe now making a comeback.

These cute walking shoes are made from Italian leather to create a beautiful plaid design.

23. Easy Spirit Gold Mary Jane Flats

The easy spirit memory foam shoes are perfect for having the right amount of comfort on the pressure points. They are lightweight shoes that have great features to help with many things such as arch support.

24. Bulo Josie Women’s Leather Mary Jane Shoe

The stitch design of these women’s shoes is a great style choice to have in your closet. The unique speckled design on the sole helps to cushion the feet for a long period of time.

The top is made from Italian leather, also leather-lined and memory foam upper.

25. Square Toe Mary Janes

This shoe comes in many different colors and has a glossy leather finish over the top. The design of these is a thin strap over the top of the foot with a small loop closure.

The square toe is another interesting feature on this shoe. These Mary Jane walking shoes are perfect for a leisure day around town.

Purchasing Mary Janes

When purchasing a pair, always be on the lookout for pro deal purchases so that you can get a better deal on your shoes. They can be found in just about any shoe store you go to, from Shoe Station to Belk these shoes are around every corner.

These are just a small list of the best Mary Jane shoes. You can find a pair of Mary Janes at any retail store around. The versatile style of Mary Janes works for any occasion!

Whether you need anatomical arch support or flexible footwear there is a right type of shoes for you!

This style of shoe is a staple piece to have in your closet. Even if you have a lot of shoes, you should have at least one pair because Mary Janes are not going anywhere.

We hope that this article helped you to find the best mary jane walking shoes for you!

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