7 Chic Ways to Style Your Flat Mary Jane Shoes
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All about flat Mary Jane shoes, and how to style your Mary Janes, so that you too can rock this fabulous retro shoes style
This post is all about retro flat Mary Jane shoes
Every woman knows that the right pair of shoes not only makes your day, but also makes your outfit.
One of the most iconic retro shoes that has withstood the test of time is the flat Mary Jane shoe style.
Even though this famous retro shoe style has been spotted as far back as Henry VIII (yeah that king who apparently had as many shoes as he had wives) yet we’re going to pick up the story of this vintage shoe in 1900.
Plus we’re going to explore how to style Mary Jane shoes with inspiration from the most iconic looks from the 1920s through the 1960s.
It’s easy to see why the Mary Jane shoe style was the go-to shoe for women across generations and has been featured on the runways across the years for brands like Gucci, Chanel, Karl Lagerfeld, and Prada.
You’ve been forewarned… fabulous retro shoe style inspo is incoming!
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“A woman with good shoes is never ugly”
Flat Mary Jane Shoes (Retro Shoes Womens): The History of the Iconic Retro Shoe
How did Mary Jane shoes get their name?
Long ago and far away… in 1902, a colorful comic strip, Buster Brown came to life.
It was about a schoolboy, Buster Brown, who played funny jokes and pranks on everyone.
His sweetheart, Mary Jane, and his doggie were his sidekicks.
These adorably dressed characters were famous and well loved in the early-20th century.
The cartoonist not only had a creative streak, but he was a smart businessman too. In 1905, he traveled to the St. Louis World fair and sold the right to use his characters to sell their products to a number of companies.
One business, Brown Shoe Company, jumped at the chance and went all out with their marketing, hiring folks to act the part of the characters and hitting up theaters and stores across the country.
Can you guess what they named the shoes that Buster Brown and Mary Jane wore? Yep, you got it… the Mary Jane!
At first they were worn both by boys and girls, but then became a favorite for girls, and by the 1920s, they became the go to choice for women too!
We love the journey and evolution of the adorable Mary Jane shoes.
They continue to be an adorable must-have for every female!
What makes a shoe a Mary Jane? What does the Mary Jane shoe look like?
Flat Mary Jane shoes are a type of flat ballerina shoe style that features a characteristic strap across the top.
They are often made of leather, and their toe may be square or rounded.
They usually have low comfy heels or are flat.
As you’ll soon discover, the feminine and practical style of the flat Mary Jane shoes makes them one of the most versatile pairs of retro shoes, as they may be paired with any outfit and look adorable or stunning, depending on the style of flat Mary Jane shoes you select, and what outfit you pair it with!
How to Style Mary Janes: #1 Wear them like Coco Chanel
Shop this flat Mary Jane Shoes style: Jeweled White Mary Jane Shoes
Gabrielle Chanel (“Coco”) was the legendary french fashion designer who founded the Chanel brand.
She not only had a knack for entrepreneurship, but an incredible eye for style.
She was bold and didn’t hesitate to break rules.
She created her N°5 perfume in 1921, which was a smashing success, and even modeled for ads for her company in the late 1930s, which unheard of at the time!
We love this retro style outfit that Coco Chanel models that emphasizes her white Mary Jane flat style shoes.
Notice how the neutral flowy shirt and full pleated skirt contrast sharply with the sleek structured shoes.
This vintage style outfit oozes casual and chic femininity, and comfort at the same time. It’d be equally perfect for leisurely sightseeing at the beach, or a romantic evening out on the town.
This adorable flat Mary Jane style is a perfect example of how Chanel designs embody both simplicity and comfort, adhering to the famous Coco Chanel quote that, “Luxury must be comfortable, otherwise it is not luxury.”
How to Style Flat Mary Janes #2: Vintage Flapper Glam
Shop this flat Mary Jane Shoes style: Black Flat Mary Jane Shoes
This Greta Garbo Mary Jane Shoes style sparkles in a delightful Old Hollywood Glamour meets Vintage Flapper Glam.
The secret to this eye turning retro style?
This vintage style outfit is a delightful study in textures, layering, and how important fashion accessories (most especially your shoes!) are to take your outfit to the next level.
Notice how Greta Garbo layers a chic retro striped skirt with an oversized fur coat, and textured scarf.
This is paired with a vintage hat, gloves, and a small clutch.
Her black flat Mary Jane shoes add the delightful pop of color and an unexpected element to her outfit.
Fun fact!
Greta Garbo became friends with the fashion designer Salvatore Ferragamo in the late 1920s Hollywood, and what did she have him do? Well, create her custom flat Mary Jane shoes of course!
P.S. Can you spot her name on the shoe molds above?
Flat Mary Jane Shoes (Retro Shoes Womens): How to Style Mary Janes #3: Flapper Workout Shoes
This is an entertaining flat Mary Jane Shoes style look…welcome to gym wear (and most notably the fashionable gym shoes!) of the 1920s!
Need to shake that stubborn fat off?
Well, what better way than to use the wooden treadmills, which some have jokingly referred to were more like ‘torture chambers’ compared to the luxury of today’s modern gyms!
Some modern day suggestions for incorporating these into your exercise routine? Barre class, your afternoon walk (to tackle those 10K steps, because you know that sitting is the new smoking), and your aerobics or dance class!
Shop this flat Mary Jane Shoes style: Black flat Mary Jane Shoes
How to Style Mary Janes #4: Vintage Schoolgirl Chic
Shop this flat Mary Jane Shoes style: Flat Mary Jane Shoes with bows
We love this flat Mary Jane shoes style… it is so simple and comfy, yet it is so vintage chic at the same time.
Notice how the girls paired their white button-up shirts with retro black shorts.
For styling their flat Mary Jane shoes, the girls either added white socks or opted to go sockless, and some added a tie detail as well.
This retro look is practical for every day casual, and especially great for the summer.
How to Style Flat Mary Janes #5: ’40s Glamour Girl
Were the Andrews Sisters Singing Trio more famous for their American musical acts in the 1940s, or how they could rock adorable flat Mary Jane shoes?
The “America’s Wartime Sweethearts” were not only favorites of American troops overseas, but they also performed in 1940s films too.
This goes to show a girl… again… just how dressy (and practical) Mary Jane flats are.
Another 1940s look for Mary Janes is showcased by the 1940 French hosiery ad included below.
Notice how the patterned hosiery is layered with shiny Flat Mary Janes for a very sexy look, which is fabulous for showing some leg under your skirts or shorts.
Other retro styling tips for your retro Mary Janes? Don’t be afraid to go shiny and strappy with your Mary Janes — it’s a delightful twist.
And yes, experiment with different hosiery styles, so you can take your favorite summer shoe into the winter season.
Shop this flat Mary Jane Shoes style: Black strappy flat Mary Jane Shoes
Flat Mary Jane Shoes (Retro Shoes Womens): How to Style Mary Janes #6: Sixties Sexpot
Shop this flat Mary Jane Shoes style: Pointed flat Mary Jane Shoes
Ouh là là this vintage sixties look absolutely sizzles, as the perfect blend of ultra mod and glam.
The leggy Jean Shrimpton was one of the world’s first supermodels, who dominating the 1960’s and 1970’s fashion scenes.
Who better to look to for some fabulous Mary Jane shoe style inspiration?
Why are the retro style elements from this look modeled by the fashion icon of Swinging London?
Shrimpton pairs a fitted classic double-breasted coat with a floppy winter hat, and brown bag.
In contrast, her patterned leggings are bright pop of white that highlight her gorgeous long legs and ultra mod flat Mary Jane shoes.
Notice the 1960s style elements for her flat Mary Jane shoes — from the pointy toe, ulta slim buckle, to the sassy angle of the low heel.
Retro style tips to recreate this look? A neutral pout, lined eyes, and a simple 1960s hairstyle.
How to Style Mary Janes #7: Sixties Siren
How could we possibly talk about vintage 1960s style without mentioning the miniskirt?
This 1960s flat Mary Jane shoes style looks so perfectly vintage mod glam when paired with a classic miniskirt.
Notice how the color selection and shape of this flat Mary Jane shoe sets this pair apart.
It is in a beautiful neutral color with a slim sassy strap and slightly angular toe shape… and of course, it has no heel!
Looking to recreate this vintage style for an Instagram worthy photo?
Select a matching monochromatic shirt and miniskirt outfit. Remember, everything matches, from your top, to your belt, to your hoes, and, most importantly to your flat Mary Jane shoes!
Shop this flat Mary Jane Shoes style: Gold flat Mary Jane Shoes
Modern way to style your Mary Janes
Remember when Taylor Swift had a passion for retro style outfits?
She would blend various vintage style elements from the 1950s and 1960s fashion.
We love these classic looks! Notice how eye turning and feminine these looks are, and yes… still comfy in flats.
This post is all about flat Mary Jane shoes, and how to style your Mary Janes, so that you too can rock this fabulous retro shoes style.
Now that you’re an expert on flat Mary Jane shoes, which retro shoe style is your favorite?
Do you prefer vintage style from the flapper era, the 1940s and 1950s schoolgirl style, or the 1960s style?
Remember, as Marilyn Monroe said: “Give a girl the right shoes, and she can conquer the world.”
Other posts you might like:
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How to Dress Like the 50s with Jeans
19 Breathtaking Grace Kelly Style Inspiration Ideas
Where to Buy Women’s Saddle Shoes & Oxfords – Your Vintage Shoe Guide
Originally published Jun 05, 2023. Updated Sep 03, 2024
