Mary Jane shoes are the ultimate classic footwear that instantly add retro charm to any outfit. With their distinctive strap and chunky block or stiletto heel, Mary Janes are versatile enough to be dressed up or down effortlessly. They look just as cute with dresses and skirts as they do with jeans and trousers, making them a wardrobe staple for women of all ages.
In this blog post, we’ll showcase 20 chic Mary Jane shoes outfit ideas to inspire your next look. Ranging from everyday casual outfits to dressy going-out ensembles, these stylish pairings prove that Mary Janes deserve a spot in every modern girl’s closet.
So read on for outfit inspiration and shoppable pieces to try the Mary Jane trend for yourself!
Mary Jane Shoes Outfit Ideas
1. Black Turtleneck and Houndstooth Set with Red Mary Janes
For our first outfit, we have a mod 60s-inspired look perfect for transitional weather.
The graphic black and white houndstooth print makes a bold statement, while the black turtleneck, cropped jacket and pleated mini skirt silhouette has a retro vibe.
Sheer black tights add coverage and the bright pop of red Mary Jane pumps pulls the outfit together. This monochrome set with a colorful shoe is an easy way to incorporate the Mary Jane trend into your fall wardrobe.
2. Gray Off-Shoulder Sweater and Charcoal Skirt with Red Mary Janes
Next up is an effortlessly chic casual outfit for laidback days. An off-shoulder sweater is a trendy cool-girl staple that looks amazing paired with any skirt.
Choose one with thick ribbed fabric in a neutral gray shade that complements the charcoal hue of the pleated mini.
Sheer black tights add subtle edge, while the red Mary Janes inject a fun pop of color. It’s a relaxed outfit that still makes a stylish statement.
3. Red Off-Shoulder Crop Top and Cargo Pants with Red Mary Janes
If you want to make more of a splash, go for an all-red monochromatic look. A cropped off-shoulder top shows just a peek of skin, balancing the loose silhouette of black wide-leg cargo pants.
In keeping with the fiery color scheme, wear red Mary Jane pumps to tie the whole outfit together. This bold head-to-toe look is perfect for making an entrance at a party or event.
4. Black Oversized Cardigan and Gingham Skirt with Black Mary Janes
For the perfect back-to-school or office outfit, layer a black oversized cardigan over a gingham print mini skirt.
The contrasting textures and patterns are so chic, while the long cardigan balances out the short hemline of the skirt.
Finish with black patent leather Mary Janes and rectangular sunglasses for a polished preppy look. This outfit works for running errands on the weekend too!
5. White Button-Up and Gray Cardigan with Black Mary Janes
Speaking of preppy style, you can never go wrong with a crisp white button-up shirt, especially when styled with proper ladylike accessories. Tuck it into a charcoal gray mini skirt, then layer on a matching knit cardigan.
White ankle socks and black Mary Jane pumps keep the look prim and proper. It’s a classic outfit combination that always looks put-together.
6. Black Ruffled Crop Top and Beige Maxi Skirt with Black Mary Janes
If you want to highlight your Mary Janes with a skirt or dress ensemble, go for neutral colors up top so the shoes stand out.
Here, a black ruffled crop top pairs nicely with a beige maxi skirt without competing for attention. The long flowy skirt provides the perfect counterbalance to show off the chunky Mary Jane block heels.
7. Gray Blazer, Vest and Jeans with White Mary Jane Pumps
Give your Mary Janes a sophisticated spin by incorporating them into a smart casual outfit with business wear elements.
A tailored gray blazer and matching button-front vest make a suit-inspired statement, while light wash jeans keep things casual.
White Mary Jane block-heeled pumps are a fresh summery choice. It’s the perfect polished outfit for a semi-formal daytime event.
8. Black Polka Dot Dress and Mary Jane Pumps
You can never go wrong with a classic polka dot dress, which pairs perfectly with Mary Janes.
The black and white print is eternally chic, while the spaghetti straps and mini silhouette have retro appeal.
Complement with black patent Mary Jane block heels and a matching black headband for a perfectly pulled-together look. This outfit works for both day and night.
9. Pink “Paris” T-Shirt, White Shorts and Red Mary Janes
Mary Jane shoes have a certain je ne sais quoi that feels fitting for a Parisian-inspired look.
Have fun with this casual summer outfit by pairing a graphic tee with “Paris” in pink script with crisp white shorts. Then let red Mary Janes be the focal point to pull the look together. It’s comfortable, playful and tres chic!
10. Black Satin Slip Dress and Pink Mary Jane
Make your Mary Janes the star of the show by pairing them with simple complementary pieces, like this black satin slip dress. The cowl neckline and spaghetti straps have timeless appeal.
It’s understated yet glamorous for cocktails or date night.
11. Black Leather Jacket, White Top and Light Wash Skirt with Black Mary Janes
Give edgy grunge style a dose of femininity with everyone’s favorite shoe—the Mary Jane!
Toughen up a crisp white collared shirt and light wash denim mini skirt with a black leather moto jacket.
Then contrast the rock n’ roll vibe with proper black Mary Janes over bright white knee-high socks. It puts a fun flirty twist on the 90s throwback look.
12. Striped Sweater, White Shirt and Blue Jeans with Red Mary Janes
Here’s another way to make your Mary Janes the focal point: pair them with basic staples in classic colors.
A white button-up shirt and dark rinse straight-leg jeans are wardrobe essentials, while a navy and white striped sweater adds preppy personality when draped over the shoulders.
Let brightly hued red Mary Janes be the star of this easy, everyday outfit.
13. Olive Dress with Lace Sleeves and Mary Jane Shoes
If you want to highlight just a hint of skin, layer a sleeveless dress over a long sleeve lacy blouse. This olive green dress gets a romantic vibe from the sheer white lace sleeves peeking out from underneath.
Keep accessories minimal to let the textures shine—simple Mary Jane shoes are all you need to finish the flirty boho look.
14. Light Blue Button-Up, Denim Skirt and Red Mary Janes
Denim skirts are the perfect canvas to style Mary Janes for an effortlessly cool look.
Here, a light wash denim maxi skirt with a front slit shows just a glimpse of leg, contrasting nicely with a light blue button-up shirt.
Make the shoes the accent piece with bright red Mary Jane pumps. Cat eye sunglasses add a retro-glam vibe.
15. Red Cardigan, Camisole, Leopard Pants and Red Mary Janes
Have fun mixing prints and textures by pairing a lacy white camisole with wildly printed leopard pants.
Layer with a bright cherry red cardigan to tie the outfit palette together. Then let equally fiery red Mary Janes be the grounding accent.
White frilly ankle socks keep the vibe light and playful. It’s a great day-to-night outfit for making a stylish statement!
16. Light Blue Gingham Dress and Black Mary Janes
You can never go wrong pairing Mary Janes with a sweet and feminine dress. This light blue gingham print mini dress features trendy puff sleeves and a smocked square neckline.
Black patent Mary Janes complement the retro silhouette, while frilly white socks add darling accent. It’s a charming look for a date or springtime picnic.
17. Oversized Red Jacket, Gray Sweatshirt and Blue Jeans with Black Mary Janes
Give your favorite casual sweatshirt and jeans combo a quick style upgrade by layering pieces in complementary colors. An oversized red jacket makes a vibrant statement over a basic gray sweatshirt.
Dark rinse skinny jeans keep things streamlined and unfussy. The perfect finishing touch? A pair of proper black Mary Jane pumps, of course!
18. Black and White Striped Cardigan, Skirt and Mary Janes
If you’re looking for an easy outfit formula, you can never fail with monochromatic neutrals plus a colorful pop.
Here, a black and white striped knit cardigan makes the perfect layer over a black mini skirt. Ground the look with matching black opaque tights and patent Mary Jane shoes for a perfectly polished ensemble.
19. Beige Trench Coat, White Sweater, Jeans and Black Patent Mary Janes
This is the ideal transitional weather outfit for staying comfortable while looking stylish.
A beige trench coat keeps things cozy yet refined over top a simple white sweater and light wash skinny jeans.
Make any outfit look instantly more put-together by finishing with black patent leather Mary Janes.
20. Beige Jacket and Trousers, Black Top and Mary Janes
Our last outfit formula is another easy go-to for looking chic on busy days: neutral pieces plus a colorful accent.
A beige cropped jacket paired with white wide-leg trousers creates a crisp, modern suiting set, perfectly grounded by a black sleeveless shell.
Complete the look with always-appropriate black Mary Jane for an effortlessly sophisticated ensemble.
