I’ll be the first to admit that when a trend from my childhood comes back, I’m a little skeptical. But hear me out because Mary Janes are the real deal.
They’ve gotten such a cool, modern update, and I’m seeing them styled in the most amazing ways. Forget what you thought you knew, because these shoes are about to become your new go-to for adding a little personality to literally any outfit.
Why Do They Call Them Mary Janes?
So, where did the name Mary Janes even come from? It’s actually a pretty cute story.
It all started with a comic strip from the early 1900s called Buster Brown. The creator, Richard Felton Outcault, drew a character named Mary Jane who was Buster’s sweetheart, and she always wore these signature shoes with a rounded toe and a strap across the top.
The Brown Shoe Company thought this was a brilliant marketing opportunity and started using the character to sell this style of shoe for kids. The name totally caught on and has been with us ever since.
Over the years, Mary Janes grew up and left the playground, becoming a seriously chic and beloved staple for women everywhere.
1. Gingham Dress + Red Mary Janes + Matching Bag
This is summer sweetness brought to life. I mean, a gingham dress paired with red Mary Janes is a combination made for picnics and garden parties. What really pulls it all together is that perfectly coordinated bag.
2. Patterned Jacket + Lilac Jumper + Beige Trousers + Blue Mary Janes
I love playing with color and texture. The powder blue Mary Janes are such a great touch, brightening up this chic layered look of neutrals and soft pastels.
3. Leather Jacket + Black Mini + White Textured Tights + Black Mary Janes
This look is so retro with a wink. The white textured tights and block heel Mary Janes give a playful mod twist to what would otherwise be a sleek, black on black outfit. Of course, the beret is included!
4. White Button-Down + Black Midi Skirt + White Socks + Black Mary Janes
Here is a polished, preppy combination. The white socks and glossy Mary Janes bring so much charm to this classic black and white ensemble.
5. Green Button-Down + Jeans + Fuchsia Espadrille Mary Janes
This outfit is so bright and playful with a bit of vintage flair. I just love how the vivid green shirt and the bold pink espadrille Mary Janes work together without ever competing for attention.
6. Chunky Knit + Mini Skirt + Socks + Red Mary Janes
This feels very schoolgirl inspired with a touch of dark academia. The chunky knits and socks help tone down the boldness of the red block heel Mary Janes. It creates a cozy, city-ready look that feels both nostalgic and modern.
7. Tweed Jacket + White Shorts + Two-Tone Mary Janes
I am obsessed with this Chanel-adjacent and effortlessly chic look. The crisp shorts, the tweed jacket, and the black and white Mary Janes are giving serious garden party energy. Or maybe a very stylish brunch.
9. All-Black Look + Red Block Heel Mary Janes
This look is minimalist, but it still has so much impact. The structured black mini and the leather trench let the glossy red Mary Janes be the star of the show. So ideal for a night out or a fashion event.
10. Striped Tee + Blazer + Red Patent Mary Janes
Here is proof that Parisian inspired style is always a good idea. The red Mary Janes really pop against the classic stripes and a tailored blazer, which makes this café look feel both polished and fun.
11. Babydoll Dress + Platform Mary Janes + Knee Socks
This is a playful nod to schoolgirl style but with a modern update. The chartreuse mini and the platform Mary Janes, especially when paired with knee socks, make this whole outfit feel fun, a little irreverent, and totally cool.
12. Leather Trench + Cargo Trousers + Black Block Heel Mary Janes
This is tough meets feminine. The oversized trench and slouchy cargos are balanced out perfectly by the structured, high shine Mary Janes. It is a styling move that feels so fresh and unexpected.
13. Black Dress + Red Tights + Classic Mary Janes
Here’s a lesson in playful layering. That pop of red tights and the glossy Mary Janes bring a festive twist to an otherwise monochrome winter look. It proves that cold weather dressing can still be a lot of fun.
14. Soft Blue Knit + Jeans + Velvet Mary Janes
This is just so understated and charming. The tonal blue palette feels completely effortless, and the velvet Mary Janes add a subtle dose of texture and polish.
15. Blazer + Tank + Denim Maxi Skirt + Black Mary Janes
What an easy balance of modern and classic. The structured blazer and the sleek black Mary Janes really ground the casual coolness of the denim maxi.
16. Graphic Tee + Jeans + Chunky Mary Janes
This off duty look gets a cool girl twist with some chunky Mary Janes and slouchy denim. The graphic tee and that ruched bag keep it playful and laid back, which is perfect for weekend wandering.
18. White Blouse + Olive Shift Dress + Brown Mary Janes
This feels modern and feminine. The delicate details and those sleek Mary Janes add a nice polish to this timeless layered look.
19. Gingham Crop Top + Leather Mini Skirt + White Socks + Black Mary Janes
Such a retro cool girl vibe. The fishnets, socks, and glossy Mary Janes bring some flirty vintage vibes to this really playful look.
20. Grey Blazer + White Trousers + Polka Dot Mary Janes
This is some unexpected fun. The polka dot Mary Janes add a bit of whimsy into this tailored, laid back brunch outfit.
21. Ruffled Blouse + Blazer + Jeans + Red Block Heel Mary Janes
A perfectly Parisian mix. The dramatic ruffled blouse and those vintage inspired red Mary Janes add a romantic flourish to this polished denim look.
22. Leather Jacket + Tailored Trousers + Silver Mary Janes
This is a masterclass in elevated casual. The leather jacket and the tailored trousers feel so sophisticated, while the silver Mary Janes bring in just the right amount of shine to tie it all together.
23. Black Jacket + Red Textured Skirt + Black Flats
This is romantic meets edgy. A bold red skirt really pops against the classic black palette and those sleek Mary Jane flats.
24. Cream Tee + Red Jumper + Blue Jeans + Burgundy Mary Janes
This is your everyday French chic. The burgundy Mary Janes and the matching accents elevate simple jeans and a tee for an effortlessly cool look.