Mary Jane shoes are about to have a big moment – just look at the runways! We’ve selected the best Mary Jane shoes you can buy right now, including Mary Jane flats, Mary Jane heels, and platforms – so you can find the perfect pair to wear for every day of the week.

Best Mary Jane Shoes to Channel Carrie Bradshaw

Then we’ll get into the surprisingly boyish history of these girlish shoes, so you’ll know where they came from. We’ve also included a style guide so you can make every one of your outfits work with the Mary Jane shoes you choose!

Mary Jane Shoes Style Guide: Contents

• 11 Best Pairs of Mary Jane Shoes to Buy in 2019
• The History of Mary Jane Shoes
• How to Style Your Mary Janes for Day and Night

11 Best Pairs of Mary Jane Shoes to Buy in 2019

We guarantee that these shoes will generate as much excitement as those Manolo Blahnik Mary Janes did for Carrie Bradshaw in that iconic Sex and the City scene.

1. Patent Red Mary Jane Shoes

These candy apple red Mary Janes will bring so much joy to your wardrobe. Expertly made of patent calfskin in France, these shoes are as high quality as can be. They have a chunky low heel that ensures they’ll be quite comfy to walk around in, and cute design that is well suited both for the street and for the office. You can order them from Shopbop.

Best Mary Jane Shoes: Repetto Mary Janes

2. Star-Studded Mary Jane Flats

Miuccia Prada is nearly single-handedly responsible for the recent popularity of these girlish shoes, so naturally Miu Miu makes some of the best Mary Jane shoes on the market. These little black patent shoes have the tiniest heel, and are embellished with crystal stars along the strap for a touch of glam. They are available through Net-a-Porter.

Best Mary Jane Shoes: Miu Miu Mary Janes

3. Double Strap Mary Jane Heels

There is a touch of Victorian charm to these heeled Mary Janes. They come in black or red, with a double strap over the foot that is secured by rounded ornamental buttons. Instead of a rounded toe, they have an almond toe that elongates the leg, and the blocky 2-inch heel adds just a bit of height without causing pain. Pick them up from Nordstrom!

Best Mary Jane Shoes: Pas de Rouge Mary Janes

4. Sharp Mary Jane Shoes

Pointed-toe Mary Jane heels might break with tradition, but they do so in a feisty way that has instant appeal. These Roger Vivier shoes also have an angled blocky heel that also adds to their unique shape, while a rose embellishment over the thick strap adds a touch of softness. Order them online via Net-a-Porter!

Best Mary Jane Shoes: Roger Vivier Mary Janes

5. Suede Mary Janes

Could these be the perfect pair of Mary Jane shoes for the office? We think they might be. Made of soft goatskin suede in timeless black, these low-heeled Mary Janes are comfortable yet elegant, with a little ribbon embellishment on the strap for a touch of whimsy. Get your pair from Shopbop!

Best Mary Jane Shoes: Loeffler Randall Mary Janes

6. Glamorous Mary Jane Heels

These are the Mary Janes you’ll want to go out in. With a 2.5-inch heel and marvelous crystal embellishment on the strap, they attract the eye and exude glamour the way Alexa Chung shoes should. They are made of gorgeous black velvet, and are perfect to pair with your favorite LBD. You can buy them from Net-a-Porter.

Best Mary Jane Shoes: Alexa Chung Mary Janes

7. Eclectic Mary Janes

Mary Jane heels don’t have to be demure or simple – they can be dramatic and unique. These Marni heels are just that, with a pointy toe, angled metallic heel, and lots of color. The design is architectural, while the colors have a ‘60s mod flare. Find them at Shopbop!

Best Mary Jane Shoes: Marni Mary Janes

8. Fringed Mary Janes

These are the best Mary Jane shoes for turning heads. The front is all elegance, made of black velvet, a delicate rounded toe, and a crystal-studded embellishment. Then the heels add an incomprehensible level of drama. They are 4 inches high, and covered in a dramatic metal fringe that will swish every which way as you walk. Get these powerful Louboutin Mary Janes at Net-a-Porter!

Best Mary Jane Shoes: Christian Louboutin Mary Janes

9. Grosgrain Strap Mary Jane Heels

These Mary Jane heels are as elegant as can be, with just one small, sporty twist. The simple, black leather pumps have a grosgrain strap in emblematic Gucci green and red stripes. These high-quality pumps are made in Italy, and have a 4.15-inch heel that will garner lots of attention. You can pop into Nordstrom to pick them up.

Best Mary Jane Shoes: Gucci Mary Janes

10. Floral Mary Jane Flats

These flats perfectly embody MJE (Mary Jane Energy), meaning that they are cute and girlish with a bit of attitude. These metallic leather shoes are covered in a delicate floral print, with a pointed toe adding a hint of edge and drama, not to mention flattering elongation. Find them online through Net-a-Porter!

Best Mary Jane Shoes: Tabitha Simmons Mary Janes

11. Emerald Mary Jane Heels

We can’t think of a pair of shoes more opulent than these emerald-colored velvet Mary Jane platforms. The blocky heel is 4 inches high and covered in shiny rhinestones, as is the brooch on the strap. Dress them up for a night out or dress them down and feel daring at the office. Get these D&G Mary Janes through Farfetch!

Best Mary Jane Shoes: Dolce & Gabbana Mary Janes

The History of Mary Jane Shoes

Mary Janes are as versatile as can be, with a few key elements that make them what they are. Mary Janes are almost always closed-toe shoes fitted with a strap over the top of the foot, and a closed back. The toe is usually rounded, although you’ll find some gorgeous exceptions, and occasionally instead of the typical strap they’ll have a T-strap.

Over the years we’ve seen Mary Jane shoes adopted by all kinds of subcultures, but let’s talk about their origin first.

The Mary Jane design was first popularized as a children’s shoe in the early 20th century, worn by both boys and girls. The design came first, of course, with many unisex shoes throughout history displaying some elements from it, while the name came second.

The History of Mary Jane Shoes

The shoes were named after one of the main characters in the Buster Brown comic strip. The comic followed the story of Buster Brown, a little boy who liked to play tricks, and his sweetheart, Mary Jane. Both children wore Mary Jane shoes in the comic, but ultimately the girl became the namesake for the shoes.

In the 1920s we start seeing Mary Jane shoes for adults, particularly as a dancing shoe for women. These low Mary Jane heels were perfect for the wild dancing styles of the swinging ‘20s because they held the foot securely and kept it protected. Even during this time, however, the shoes still remained a childhood staple, with Shirley Temple wearing them in her performances in the ‘30s.

In the 1960s Mary Jane shoes became associated with high fashion and the mod styles, with Twiggy wearing them for fashion shoots and making them popular.

Mary Jane shoes took a back seat in the ‘70s and ‘80s, but in the ‘90s they were popularized once again, with Courtney Love in particular taking a liking to them. By styling them with socks and extra short dresses, she presented a striking combination of girlish and sexy that was very subversive at the time.

How to Wear Mary Jane Heels

It’s interesting to note that across these decades Mary Jane shoes kept coming back with similar silhouettes: the rounded-toe Mary Janes were consistently paired with short, straight-waist dresses, embodying a style that is at once youthful yet mature.

These days the Mary Jane strap can be added to shoes with all kinds of silhouettes, but stick to that rounded toe box if you want to embody the subversive style of the ‘60s and ‘90s.


How to Style Your Mary Janes for Day and Night

Mary Janes are a very versatile shoe that is easy to dress up from day to night and from the street to the office. Here’s our advice on how to wear them for every occasion.

Casual

• Any style of Mary Janes can work for casual streetwear, so feel free to go wild with the designs and don’t be afraid of anything being too cutesy or childish.

• Mary Jane flats are perfect for dressing up a pair of boyfriend or straight-leg jeans.

• For pairing with skinny jeans, opt for almond or pointed-toe Mary Janes rather than rounded-toe ones.

• Colorful Mary Jane shoes are perfect for color blocking! Opt for a bright pair to wear with a summery, colorful outfit. Use the color wheel and read our article about color blocking to come up with different combinations.

How to Style Mary Jane Shoes

• If your style is a little flowier and more boho-chic, opt for light-colored Mary Janes made of suede, fabric or raw leather.

• If you’re wearing your Mary Janes with a skirt, consider adding a pair of fun knee-high socks or colorful tights for a girlish look.

• If you have a more preppy style, wearing your Mary Janes with a cardigan is a guaranteed win – this look will work with both skirts and pants.

• Chunky Mary Jane platforms are perfect for bringing back some ‘90s style, especially if you pair them with a pair of socks and a shorter dress.

Professional

• Both flat and low-heeled Mary Janes are excellent for office wear!

• Opt for a pair that is sophisticated, made of a solid color rather than covered in print. Avoid excessive embellishments.

• Pointed, almond, and square-toed Mary Janes tend to look more mature, especially if they are flat. High-heeled Mary Janes are usually fine with any toe style.

How to Wear Mary Janes

• Pair your Mary Janes with any of your work outfits – they look just as nice with trousers as they do with skirt suits.

• Beige Mary Janes will work with both darker and lighter suits, though otherwise you should match dark shoes to dark outfits and light shoes to light outfits.

• If you’re wearing your Mary Janes with a skirt, you might want to also add pantyhose or a pair of tights to the look.

• Mary Janes with low, blocky heels are perfectly acceptable for office wear, while if you like a higher pump then opt for a thinner stiletto.

Club

• Mary Jane flats are perfectly fine to wear to a night out, but a pair of high Mary Jane platforms will make you feel infinitely sexier.

• Choose Mary Janes with a strap that sits a little lower on the foot, especially if you’re wearing a dress or skirt with a short hemline, as a strap that sits too high will cut off the leg and make it seem shorter.

How to Style Mary Jane Heels

• For a classier look opt for Mary Janes made of velvet, while patent leather is perfect if you prefer a more modern vibe.

• For a feminine club look that is a little risqué, style your Mary Jane shoes with a short pleated skirt or dressy shorts and a blouse tucked in.

• For a more grown-up look, rock you Mary Jane platforms with a tight-fitting bodycon dress – short or long is up to you.

• There is something deliciously risqué about pairing Mary Jane platforms with a pair of fishnet stockings, while if you’re going out on a colder night you might prefer a pair of opaque tights instead.

Dressy

• Sleek Mary Jane heels are usually more elegant than Mary Jane platforms.

• It’s better to choose Mary Janes with a thinner strap that sits lower on the foot, as they usually have a more delicate appearance.

How to Wear Mary Jane Shoes

• If your dress is simple you can opt for more unique Mary Janes, with a lot of glamorous embellishments or a dramatic shape.

• If you’re wearing a highly embellished or complex dress then it’s better to choose simple, solid-colored Mary Janes.

Photos via @elle_ferguson, @carajourdan, @cocobassey, @notyourstandard, @blaireadiebee, @vivaluxuryblog