Sure, a Mary Jane is fairly straightforward to style, but knowing what to pair it with so it feels modern can be a whole other challenge.
Since this will be my go-to shoe choice for the unforeseeable future, I thought I’d round up a handful of cute Mary Jane outfit ideas.
Whether you’re looking for a chic work outfit or something easy yet elevated to throw on during the weekends, you’ll find inspo here.
1. Slip into Elegance
A black satin slip dress with spaghetti straps is just one of those pieces that always gives off a sleek vibe. I think the addition of pink Mary Jane flats brings such a soft, feminine quality to this elegant outfit.
This would be a perfect combination for a cocktail party or a romantic dinner date.
2. Grunge Meets Prep
I love an outfit that mixes two totally different styles. Start with a light wash denim jacket over a simple black turtleneck top.
Pairing that with a plaid mini skirt gives it a fun, grunge-inspired feel, but the black Mary Jane shoes are what really add that preppy finishing touch.
3. Edgy Schoolgirl Chic
This look is all about balancing edgy and feminine pieces, and I am so here for it. Layer a black leather jacket over a classic white t-shirt for that rebellious feel, then add a gray mini skirt for a playful vibe.
The real showstoppers are the red Mary Jane shoes, which make the whole outfit pop. It’s an amazing choice for a concert or a fun night out.
4. Cream and Beige Elegance
For a look that feels seriously polished and sophisticated, you can’t go wrong with this combination. A cream sleeveless vest top looks so chic with a beige midi skirt.
To give it that classic feel, finish the outfit with black Mary Jane shoes and a matching black handbag to create a really balanced color palette.
5. White Shirt and Black Pencil Skirt
Talk about a professional look with a sultry twist. A white button-up shirt tucked into a black pencil skirt that has a thigh-high slit is such a statement.
I love that the black Mary Jane shoes add just a little touch of modesty that balances out the whole ensemble. This is definitely what I’d wear to a big business meeting.
6. Retro Picnic Vibes
I am obsessed with the vintage charm of this outfit. A gingham mini dress is already adorable, but when you accessorize it with a red shoulder bag, it gets even better.
The red Mary Jane heels are the perfect complement to the bag and give this retro-inspired look such a playful feel. This just screams summer picnic or daytime garden party.
7. Grandpa Chic
The grandpa core trend is so fun, and this is such a great way to try it out. Layer a gray cardigan over a simple black collared top and pair it all with some plaid wide-leg pants.
The black Mary Jane shoes are what really give this trendy outfit a youthful twist. I think this would be the perfect look for a day of vintage shopping or a cozy cafe date.
8. Striped Casual Chic
You can never go wrong with a casual look that still feels put-together. I love a black and white striped crop top paired with gray wide-leg pants for a comfortable base.
Adding black Mary Jane shoes is what gives this easy outfit a little touch of elegance. This is such a go-to for a day of shopping or meeting friends for coffee.
9. Blazer and Mini Skirt Combo
For an office-appropriate look that is still incredibly chic, try layering a beige oversized blazer over a crisp white button-up shirt.
When you pair it with a black mini skirt and black Mary Jane shoes, you get an outfit that just works. This combo is ideal for important meetings or presentations.
10. Summer Romance
How dreamy is this summer look? A white strapless crop top paired with a tiered white maxi skirt is just so beautiful.
The red Mary Jane shoes are what really give it that pop of color and a romantic feeling. I would totally wear this to a beach wedding or a summer garden party.
11. Oversized Sweater and Shorts
Some days just call for an outfit that’s both comfortable and stylish. A gray oversized sweater with black shorts is the perfect solution for a relaxed look.
The black Mary Jane shoes are what really add that sweet, feminine vibe. This one is a no-brainer for a lazy Sunday or a casual movie night with friends.
12. Preppy Stripes
Here’s a simple preppy outfit formula that is always a hit. Just take a light blue striped button-up shirt and pair it with a classic black pleated mini skirt.
The white Mary Jane flats are what really keep this look feeling fresh and youthful.
13. Burgundy Beauty
I am so into this rich, autumnal look. A burgundy button-up vest paired with a cream maxi skirt is such a beautiful combination.
The best part is how the burgundy Mary Jane shoes and the matching handbag pull the whole coordinated ensemble together. This is a great option for a fall wedding or an upscale brunch.
14. Cozy Blue Coordinates
You can totally embrace a cozy and casual vibe with a light blue knit sweater and matching light blue shorts.
A monochromatic look like this is always so chic, and the beige Mary Jane shoes add the perfect subtle contrast. This outfit would be ideal for a relaxed weekend brunch or just running errands in style.
15. Classic Casual
It really doesn’t get more classic than this. A simple white t-shirt and light wash wide-leg jeans are closet staples for a reason. When you layer a beige trench coat on top, the whole look feels instantly elevated.
White Mary Jane flats are the perfect shoe to complete this timeless outfit. This versatile combo works for everything from running errands to a casual lunch with friends.
16. All-Black Blazer Ensemble
For a sleek and sophisticated outfit, try this all-black look. A black blazer worn over a black lace camisole looks amazing with black shorts.
I think the black platform Mary Jane shoes are what really add some height and drama to the monochromatic ensemble. This is the perfect outfit for a gallery opening or a fancy dinner date.
17. Preppy with a Twist
I love a good preppy-inspired look. Layering a leopard print vest over a classic white button-up shirt is such a fun way to mix things up.
Pair it with some light wash mom jeans for a comfortable feel. The red Mary Jane flats are the key here, adding that essential pop of color that completes the whole look.
18. Monochrome Elegance
This is such a sophisticated outfit combination. Layer a long black coat over a black camisole top and pair it with some cream wide-leg pants for contrast.
The black Mary Jane shoes are what really ground this look and pull it all together. This would be a perfect choice for a gallery opening or a fancy dinner party.
19. Polka Dot Blouse and Pleated Skirt
What a fun combination for a look that’s both playful and sophisticated. A black polka dot blouse with a black pleated mini skirt and black tights is already a great base.
Adding the black Mary Jane shoes is just the finishing touch this outfit needs. I think this look is ideal for a day at the office or dinner with colleagues.
20. Wild and Free
This is such a bold and fun outfit. A white crop top with text on it looks so cool with a leopard print maxi skirt.
The red Mary Jane flats are what really give it that pop of color while also keeping the whole look feeling grounded. This is the perfect outfit for a music festival or a day of sightseeing in a new city.