How to Style Mary Jane Flats with Literally Anything

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If there’s one pair of shoes that always makes me smile when I slip them on, it’s Mary Janes. Maybe it’s the nostalgia, maybe it’s the way the rounded toe and strap strike that perfect balance of sweet and polished, but Mary Jane flats are having a moment – and honestly, they deserve it. 

I first got hooked on Mary Janes when I got this light brown mesh pair last year. Then I got these suede Mary Janes I’m wearing above in two colors (they’ve become my most-worn favorites!), and now I guess you could say I’m trying to build out my Mary Jane collection (I think I need a leather pair like these next)!

They’re timeless, versatile, and surprisingly easy to wear with just about everything in your wardrobe. Whether you lean preppy, minimalist, or a little romantic, a pair of Mary Janes can pull your outfit together without trying too hard.

Let’s talk about how to style Mary Jane flats with literally anything.

How to Style Mary Jane Flats

With Kick out Crop Jeans

This is probably my favorite (and most common) way to style Mary Janes because it’s so approachable but elevates an otherwise basic outfit. A good pair of denim plus a crisp t-shirt and Mary Jane flats is an easy, everyday outfit that looks more intentional than sneakers but doesn’t feel overdressed.

Straight-leg jeans like these and cropped denim (these Mother jeans are perfect) both highlight the shoe’s delicate strap, while barrel-leg jeans or wide-leg denim give you a fun contrast between slouchy and polished. You can even layer in socks if you want to lean into that Parisian vibe (I honestly love it). Add a blazer or cardigan, and suddenly your t-shirt-and-jeans uniform feels elevated.

Try this combo: light-wash straight jeans, a white tee tucked in (these are the best $14 white tees from Amazon), black leather Mary Janes, and a thin belt. Effortless but chic.

More styling tips: Here’s how to style a cardigan and the best jeans you should have in your closet.

With Wide Leg Jeans 

Wide-leg jeans are pretty hard to beat, and pairing them with Mary Jane flats strikes the perfect balance between relaxed and refined. Heavier denim contrasts beautifully with the slim, delicate profile of Mary Janes, making the shoe stand out without competing with the pants.

If your jeans are extra long, let them skim the floor so just the rounded toe peeks out to give it that effortlessly cool, model-off-duty vibe. Cropped wide-leg styles like these, on the other hand, highlight the strap detail and make your Mary Janes the star of the outfit. So either way, it’s a win.

For an easy everyday look, tuck in a simple t-shirt or ribbed tank, add a leather belt (this is my favorite classic leather belt), and finish with a pair of black or neutral Mary Janes. If you want something more elevated, swap in a crisp button-down like this one from Frank & Eileen or a blazer. Either way, Mary Janes are the perfect addition to keep wide-leg denim from feeling sloppy.

More styling tips: Here’s a guide on the best wide-leg jeans and how to style them.

With a Mini Dress or Mini Skirt

Mary Janes naturally pair with shorter hemlines because they balance proportions so well. A mini dress with ballet-flat style Mary Janes feels youthful without being juvenile, especially if you keep accessories modern (one of many polished fall outfit ideas). Think an oversized blazer, sleek crossbody, or a leather shoulder bag – this is one of my favorite shoulder bags, and you can use code TERILYN10 for 10% off.

The strap detail also grounds shorter skirts, keeping them from feeling too dressed up. And if you want to soften the look, a suede or pastel-colored pair adds just the right amount of charm.

Pro tip: If you’re worried about minis feeling too bare, add sheer tights (these tights are great and $15). They make the whole ensemble look pulled together and season-appropriate.

More styling & shopping tips: See my post on the Best Tuckernuck Dresses – that’s wear I buy 90% of my dresses and skirts!

With a Midi or Maxi Dress

Midi dresses are everywhere right now, from flowy floral styles to sleek slip dresses. The challenge with a midi or maxi is often footwear because sneakers can feel too casual, and heels too much. Enter Mary Jane flats. I wear Mary Jane flats with a midi dress for family photos last year and it worked perfectly – elevated but practical (which is necessary with two young boys). 

The rounded toe and low profile balance out the longer hemline, and you can play with textures depending on the look you’re going for. Leather Mary Janes add a sleek vibe to a suede skirt. Soft suede works with a cotton or knit ribbed dress.

If you love ballet flats but want something a little more substantial, Mary Janes give you that same feminine energy with a bit of extra structure. (Or, go for loafers – here’s how to style those.)

More styling tips: My posts on What to Wear for Family Photos and my Hill House Nap Dress Review (my favorite midi dress) include the midi dresses I love most! I also put together this post with other shoes to wear with maxi dresses that I hope is helpful!

With Trouser Shorts

Styling Mary Janes with shorts may not be the first thing that comes to mind, but it’s actually a look that feels tastefully fresh. Tailored trouser shorts (these are the trouser shorts I love most) with a cardigan and Mary Janes read as polished daywear, perfect for brunch or a casual meeting.

Denim cutoffs with a tee and Mary Janes give you a laid-back summer vibe that feels European-inspired. Add a woven tote and oversized sunglasses, and you’re basically on holiday, even if you’re just running errands. (And if you are headed to Europe, here’s what to wear.)

Styling tip: Go for higher-waisted shorts to elongate your legs when wearing Mary Janes, since the strap can visually cut across the foot.

With Trousers

Nothing says timeless like a pair of trousers with Mary Jane flats. Whether it’s pleated wide-leg pants like these I have or sleek ankle-length trousers, Mary Janes ground the look without overpowering it.

If you work in a business casual environment, this combo is a dream. Add a tucked-in t-shirt, button-down, or even a fine knit polo, and you’re set. 

Try this outfit: black trousers, cream silk blouse, burgundy Mary Jane flats. Classic but with a pop of personality.

With a Blazer

The blazer-and-Mary Jane pairing is perfect if you’re into that slightly preppy style. The sharp lines of the blazer balance the soft, rounded toe of the shoes. You can go all in with trousers underneath, or make it playful with a mini skirt.

An oversized blazer layered over denim and a tee becomes instantly cooler with Mary Jane flats instead of sneakers. I got this blazer from Nordstrom last year and it’s been the one I pull most!

More Styling Tips: See my post on What to Wear Under a Blazer, 8 Fall Fashion Trends that are Actually Wearable (including blazers), and Preppy Wardrobe Staples

With Tights

Mary Janes and tights are like peanut butter and jelly: they just belong together. The strap of the shoe breaks up the leg line in such a flattering way, and tights let you wear your Mary Janes year-round.

Black opaque tights with black Mary Janes create a sleek, leg-lengthening effect. Sheer tights feel elevated and chic. 

This is also the easiest way to winterize your mini skirts and dresses. You’ll feel put together, even when the temps drop.

Final Thoughts

At the end of the day, the reason Mary Janes work with literally anything is their design. The rounded toe is flattering without being too girly. The strap adds visual interest and keeps the shoe secure. And because they come in so many materials – patent, leather, suede, even canvas – you can find a pair to match any wardrobe.

They bridge the gap between casual and dressy in a way few other shoes can. Swap sneakers for Mary Janes, and suddenly a basic outfit looks intentional. Skip heels and choose Mary Janes, and you’ll feel comfortable (which is a must these days) but still elevated.

Whether you go for classic black leather, a jewel tone suede, or a soft pastel canvas, a pair of Mary Jane flats is one of those footwear staples that will (and should) earn its spot in your closet.