Mary Jane shoes are making a major comeback! With their cute rounded toe and distinctive strap across the instep, Mary Janes are the ultimate feminine shoe. They look great paired with dresses, skirts, jeans – you name it!
In this blog post, I’ll be sharing 28 chic Mary Jane shoes outfits to give you tons of inspiration on how to wear these cute shoes. From casual daytime looks to dressy evening outfits, I’ve covered all the bases to help you style your Mary Janes with confidence this season.
You’ll find outfit ideas featuring different colors and styles of Mary Janes, from the classic black patent leather to fun modern prints. I’ll also suggest different tops, bottoms, jackets, and accessories to complement each look.
So, whether you just got a new pair of Mary Janes and need styling tips, or you’ve had them in your closet for ages but always struggle with how to wear them, this roundup has got you covered! Read on for 28 fabulous Mary Jane outfit ideas you’ll be excited to recreate.
Mary Jane Shoes Outfit Ideas
1. Knit Sweater and Straight-Leg Trousers
For a polished and comfortable look, pair a cozy knit sweater with tailored straight-leg trousers. Choose a sweater in a neutral tone like cream, beige, or soft gray to keep the outfit versatile. The straight-leg trousers should hit just above the ankle to showcase your Mary Janes.
I love how white platform Mary Janes add a modern twist to this classic combination. The chunky sole gives you a height boost while maintaining comfort.
Complete the look with some sporty sunglasses for a touch of cool-girl edge. This outfit works great for the office, lunch dates, or even casual Fridays.
2. T-Shirt Dress and Oversized Blazer
This outfit perfectly balances comfort and style. Start with a simple t-shirt dress in a solid color or subtle print. The dress should hit mid-thigh to knee-length for the best proportion with Mary Janes.
Layer an oversized blazer over the dress for a chic, put-together look. Black Mary Jane shoes ground this outfit beautifully. They add a touch of sophistication without being too formal.
Accessorize with black sunglasses and a small handbag to tie the look together. This versatile Mary Janes outfit works for various occasions, from office meetings to weekend brunches.
3. Trench Coat and Light Blue Jeans
Here’s a fantastic example of how to wear Mary Jane shoes with jeans. Start with a pair of light blue jeans – they could be straight-leg, bootcut, or even mom jeans. Pair this with a crisp white top, which could be a button-down shirt, a simple tee, or even a lightweight sweater.
Layer a classic trench coat over the top. While the outfit in our list features a beige trench, don’t be afraid to experiment with other colors like navy, black, or even a bold red. Black Mary Jane shoes complement this outfit perfectly, adding a touch of elegance to the casual jeans.
This Mary Janes with jeans outfit is perfect for running errands, casual Fridays at work, or weekend outings.
4. Light Blue Denim Jacket and Jeans
This outfit is a fresh take on the classic Canadian tuxedo, elevated with Mary Janes. Start with a pair of light blue jeans – straight leg or slim fit works best here. Match it with a light blue denim jacket for a coordinated look. Underneath, wear a simple white top to break up the denim and add brightness to the outfit.
The star of this Mary Jane outfit is the red Mary Jane shoes. They add a vibrant pop of color that really makes the outfit stand out. Pair them with white socks for a cute, slightly retro vibe.
Accessorize with a small red handbag to match your shoes and add some cool sunglasses for a touch of glamour. This outfit is perfect for casual weekends, outdoor events, or even music festivals.
5. Black Sleeveless Top and White Midi Skirt
For a classic, feminine look, pair a black sleeveless top with a white midi skirt. Add a black belt to cinch in your waist and tie the look together.
Black Mary Jane shoes are the perfect finishing touch for this outfit. They echo the color of the top and belt, creating a cohesive look from head to toe. A black shoulder bag completes the ensemble, making it perfect for everything from office wear to dinner dates.
This Mary Jane shoes outfit is a great choice for those who love a timeless, elegant style. It’s versatile enough to wear to the office, out for drinks, or to a summer wedding. You could even switch up the color scheme – try a white top with a black skirt for a reverse effect!
6. Beige Short Jacket and Wide-Leg White Trousers
This outfit exudes sophistication and style. The beige short jacket adds structure to the look, while the wide-leg white trousers create a flowing, elegant silhouette. Underneath the jacket, opt for a dark top to create contrast. Black Mary Jane shoes perfectly complement this ensemble, adding a touch of classic charm.
Carry a small black handbag to tie the look together. This outfit is perfect for a business casual setting or a chic lunch date. You might love trying different color combinations too – perhaps a navy jacket or even a bold red one for a pop of color.
7. Light-Color Shirt Dress
A light-colored shirt dress paired with dark Mary Jane flats is the epitome of effortless chic. The dress should hit just above or below the knee for the most flattering look. Choose a dress with buttons down the front for added interest.
This Mary Jane outfit is versatile enough for various occasions – from office wear to weekend brunches. You could add a belt to cinch in the waist or leave it loose for a more relaxed vibe. Don’t forget to accessorize with some delicate jewelry to complete the look.
8. Cropped Tank Top and Striped Wide-Leg Pants
For a fun and breezy summer look, pair a cropped tank top with striped wide-leg pants. While the outfit in our list features a white tank, don’t be afraid to experiment with different colors to complement the stripes in your pants.
White Mary Jane flats add a touch of retro charm to this outfit. This look is perfect for a casual day out or a beach vacation. You could add a wide-brimmed hat and some statement earrings to elevate the outfit even further.
9. White Tank Top and Loose-Fitting Denim Culottes
This outfit is all about comfort without sacrificing style. The white tank top keeps things simple on top, while the loose-fitting denim culottes add an interesting silhouette. Mary Jane flats in a neutral color work perfectly with this look.
Add a shoulder bag and some white socks peeking out above your Mary Janes for a cute, slightly preppy vibe. This is a great example of how to wear Mary Jane shoes with jeans in a modern, fashion-forward way.
10. Striped Cardigan and High-Waisted Blue Jeans
A striped cardigan paired with high-waisted blue jeans creates a classic, timeless look. The vertical stripes on the cardigan elongate your silhouette, while the high-waisted jeans accentuate your waist.
Red Mary Jane flats add a pop of color to this outfit, making it more playful and fun. Match your shoes with a small red shoulder bag for a coordinated look. This Mary Janes outfit is perfect for a casual day out or a coffee date with friends.
11. Oversized Blazer and Striped Shorts
For a preppy yet relaxed look, pair an oversized blazer with striped shorts. While our list suggests a beige blazer, feel free to experiment with other colors like navy, black, or even pastel shades. Underneath, wear a white graphic t-shirt for a casual touch.
Red Mary Jane flats add a fun pop of color to this outfit. Complete the look with dark sunglasses and a small black handbag. This outfit is perfect for a summer day out or a casual meeting.
12. White Cropped Tie-Front Blouse and Denim Mini Skirt
This outfit is flirty and feminine, perfect for warm weather. The white cropped tie-front blouse adds a touch of retro charm, while the light blue denim mini skirt keeps things casual and fun.
Bright red Mary Jane shoes make a bold statement and tie the whole look together. Add white socks for an extra cute touch. A small black handbag completes this Mary Jane outfit perfectly. It’s ideal for a weekend outing or a casual date.
13. White Maxi Dress and Sleeveless Sweater Vest
For a boho-chic look, pair a flowing white maxi dress with a beige sleeveless sweater vest. This combination creates an interesting layered effect while keeping you cool in warmer weather.
Leopard print Mary Jane flats add a fun, unexpected twist to this outfit. Square sunglasses complete the look, giving it a trendy edge. This outfit is perfect for a summer garden party or a day out shopping.
14. Striped Long-Sleeve Top and Gray Midi Skirt
This outfit is a great example of how to mix patterns subtly. The white and black striped long-sleeve top pairs beautifully with a gray midi skirt. The key is to keep the stripes thin and the gray a solid color to avoid clashing.
Black Mary Jane shoes ground this outfit nicely. Add a structured black handbag to complete the look. This ensemble is perfect for the office or a more formal daytime event.
15. Black Graphic T-Shirt and High-Waisted Loose-Fitting Jeans
For a casual, edgy look, pair a black graphic t-shirt with high-waisted loose-fitting jeans. The contrast between the fitted top and loose jeans creates an interesting silhouette.
Red Mary Jane shoes add a pop of color and femininity to this otherwise casual outfit. This is a great example of how to wear Mary Jane shoes with jeans for a more relaxed, everyday look.
16. Black Blazer-Style Jacket and Matching Short Skirt
This outfit is perfect for a night out or a more formal event. The black blazer-style jacket paired with a matching short skirt creates a sleek, coordinated look. Add sheer black tights for extra sophistication.
Red Mary Jane heels add a pop of color and a touch of playfulness to this otherwise all-black ensemble. A small black handbag completes the look perfectly.
17. Polka Dot Dress
A polka dot dress is a timeless choice that pairs beautifully with Mary Janes. Opt for a dress with long sleeves and a midi-length skirt for a classic look. The polka dots can be any color, but black and white is always a safe bet.
Nude Mary Jane shoes complement this dress perfectly, elongating your legs and keeping the focus on the dress. This outfit is versatile enough for both casual daytime wear and dressier occasions.
18. Sleeveless Tailored Shirt and White Mini Dress
For a fresh, summery look, layer a sleeveless tailored shirt over a white mini dress. This combination creates an interesting, layered effect that’s perfect for warmer weather.
Black Mary Jane shoes add a touch of sophistication to this otherwise casual outfit. A small white handbag completes the look. This ensemble is great for a summer party or a day out in the city.
19. Black Fitted T-Shirt and White Tennis Skirt
This outfit combines sporty and feminine elements for a unique look. Pair a black fitted t-shirt with a white tennis-style skirt for a classic contrast. Add white knee-high socks for a preppy touch.
Black platform Mary Jane shoes elevate this outfit (literally and figuratively!). A black handbag ties the look together. This ensemble is perfect for a casual day out or a sporty-themed event.
20. Sleeveless White Blazer Dress
A sleeveless white blazer dress is a chic, modern choice that works well for both business and social occasions. The crisp white color keeps things fresh and summery.
White Mary Jane shoes create a monochromatic look that’s very on-trend. Add a small cream-colored handbag to complete the outfit. This look is perfect for a summer office party or a fancy lunch date.
21. Casual Flowy Floral Midi Dress
A casual flowy floral midi dress is a summer staple that pairs beautifully with Mary Jane shoes. Choose a dress with a mix of colors to give you more shoe options.
Mary Jane shoes in a color that complements the dress will tie the whole look together. This outfit is perfect for a summer wedding, garden party, or any outdoor event.
22. Fitted Romper
A fitted romper is a playful choice that looks great with Mary Janes. While our list suggests a mustard yellow romper, feel free to choose any color that suits your style. The key is to ensure it fits well and flatters your figure.
Bright red Mary Jane shoes add a fun pop of color to this outfit. Large circular earrings complete the look, adding a touch of glamour. This ensemble is perfect for a summer festival or a casual day out.
23. Cropped Black Jacket and Wide-Leg Jeans
For an edgy, street-style look, pair a cropped black jacket with light wash wide-leg jeans. This combination creates an interesting contrast between fitted and loose elements.
Black Mary Jane flats keep the look grounded and comfortable. Add dark sunglasses and a black handbag for a cohesive look. This outfit is great for a day of shopping or a casual lunch with friends.
24. Oversized Button-Up Shirt and White Shorts
An oversized button-up shirt paired with white shorts creates a relaxed, beachy vibe. While she is wearing a bright green shirt, you could opt for any color you like – pastels work particularly well for this look.
Brown Mary Jane sandals add a touch of sophistication to this casual outfit. This look is perfect for a beach vacation or a relaxed summer day.
25. Sleeveless Red Top and Voluminous White Maxi Skirt
This outfit combines a fitted sleeveless red top with a voluminous white maxi skirt for a dramatic, eye-catching look. The contrast between the fitted top and flowing skirt creates a beautiful silhouette.
Black Mary Jane flats keep the outfit grounded and comfortable. This ensemble is perfect for a summer wedding or a fancy outdoor event.
26. Gingham Check Babydoll Dress
A gingham check babydoll dress is a cute, retro-inspired choice that pairs perfectly with Mary Janes. While she is wearing a blue and white gingham, you could opt for any color combination you like.
Black Mary Jane flats add a classic touch to this playful outfit. This look is great for a picnic, a casual date, or any daytime summer event.
27. Black Leather Jacket and Straight-Leg Jeans
For an edgy, rock-inspired look, pair a black leather jacket with straight-leg jeans. This combination is classic and cool, perfect for a night out or a concert.
Black Mary Jane shoes with white socks add an unexpected twist to this outfit, softening the edgy vibe slightly. This is another great example of how to wear Mary Jane shoes with jeans for a more alternative look.
28. Gingham Check Button-Up Shirt and High-Waisted Jeans
Finally, pair a gingham check button-up shirt with high-waisted jeans for a casual, preppy look. Tuck the shirt in halfway for a relaxed vibe.
Bright red Mary Jane shoes add a pop of color to this otherwise neutral outfit. This look is perfect for a casual day out or a relaxed weekend brunch.