Do you ever look at your closet and say to yourself, "I have no practical shoes to wear?" Because let me tell you, I sure have. Curating a collection of fashionable and functional footwear can sometimes be challenging, even for an editor. I'm often swayed to test-drive another shoe trend easily or even buy another pair of heels (despite already owning too many that are far too uncomfortable). So you can understand why the need to invest in timeless and comfortable shoes is of the utmost importance, and luckily for me, one shoe style has made a subtle comeback: Mary Jane shoes. It's not that this classic shoe ever went out of style, but with the focus on trendier styles (ahem, platform sandals and ballet flats), the Mary Jane shoe style wasn't entirely a part of the conversation.
Considering that these shoes have been spotted in recent runway collections and the fashion set has fastidiously taken up wearing them, it's safe to say that Mary Janes are starting to get the recognition they deserve. After all, this style is arguably one of the best shoe purchases you can make, but it also has infinite styling possibilities. In an effort to prove my point, I've rounded up 17 Mary-Jane-shoe outfits that can be worn year-round and shopped out the key pieces needed to re-create the looks for yourself. Buckle up. After you read this, you'll no longer be able to say you have no comfy yet cute shoe options.
White Button-Down + Denim Miniskirt + Woven Bag + Mary Jane Heels
You know a shoe style is worth a try when it's spotted on the French fashion set, and such is the case with Mary Jane shoes. Take a cue from the look above and opt for a heeled pair with a white button-down and denim miniskirt for an effortlessly chic ensemble.
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The cost per wear you'll get out of these shoes makes the price tag well worth it.
I can assure you this will look good with any pair of Mary Janes.
Tank + Pencil Skirt + Crossbody Bag + Chunky Mary Jane Shoes
What's so wonderful about this shoe style is that it really does elevate every look. Case in point: the outfit above. A simple tank top and pencil skirt become a look when styled with chunky MJs.
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A simple tank will make your shoes pop even more.
Don't these look so cozy?
Oversize Blazer + T-Shirt Dress + Mary Jane Flats
What's another simple way to incorporate Mary Jane shoes into your life seamlessly? Pair them with a T-shirt dress, oversize blazer, shoulder bag, and sunglasses. This outfit is easy to throw on and embodies that cool, French effortlessness.
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These will match everything you already own.
I love a good blazer, clearly.
Oversize Sunglasses + Button-Down + Biker Shorts + Mary Jane Shoes
Some may think magic doesn't exist, but I'm pretty sure that's just because they don't own a pair of Mary Janes. This shoe style can magically transform wardrobe staples like cycling shorts and an oversize button-down from plain to polished simply by wearing them. They may not be Dorothy's red slippers, but they're magic nonetheless.
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Now here's a button-down begging to be worn with a pair of MJs.
Pro tip: Match your shoes with your oversize button-down to take your look to the next level.
Button-Down + Tie + Baby Doll Dress + Sheer Knee-High Socks + Mary Jane Shoes
Let me share a little fun fact with you: Mary Jane shoes date back centuries but rose to popularity in the 1920s as the predominant shoe style for children. So when styling these shoes, there's no better way to pay homage to their history than with a school uniform look. Pair yours with a button-down, baby doll dress, and even finish the outfit with a tie and socks, and you'll ace the assignment.
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School may be out, but these shoes are seasonless.
Pairing knee-high socks with your Mary Jane shoes is bound to secure you some compliments.
Blazer + T-Shirt + Pleated Miniskirt + Mary Jane Flats
If you don't want to have full flashbacks to your youth but still want to tap into the school-inspired aesthetic, look no further than the outfit above. Pairing a pleated miniskirt with a T-shirt, blazer, and Mary Jane shoes will give you that same preppy aesthetic without feeling too kitschy.
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This pleated miniskirt is so good that I caved and bought it in multiple colors.
The split-toe detail on these makes them truly special.
Sporty Sunglasses + Knit Top + Jeans + Socks + Mary Jane Platforms
PSA: Mary Jane shoes aren't just "sweet little schoolgirl" shoes. Brands across the board, from Versace to Jeffrey Campbell, have taken these sweet shoes into spicy territory by adding a platform, and the fashion set is eating it up. If you're unsure of how to make this edgier take on the shoes work, I recommend styling a romantic sweater and jeans with an edgy pair of shades and platform MJs. If you do this, you'll attain the perfect balance of sweet and salty wrapped up in a delectable outfit.
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These come in four other colors in case you're not a fan of white.
Statement shoes deserve to be styled with bold sunglasses.
Peter Pan Blouse + Minidress + Printed Tights + Mary Jane Heels
Another unique way to style these shoes is by leaning into their inherent quirkiness. Pair them with an oversize Peter Pan blouse, black minidress, and printed tights and you'll be wearing these shoes—not the other way around.
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Styling hack: You can also forgo the dress and pair this with a miniskirt for an equally cute way to style your MJs.
Affordable and cute? *Adds to cart ASAP.*
Tweed Jacket + Tweed Dress + Layered Necklaces + Mary Jane Heels
While more trend-forward iterations of Mary Janes have begun to bubble up, if you're a staunch classicist, you'll want to reference classic Chanel looks when styling this footwear. Pair a matching tweed jacket and dress with layered jewelry and minimal-heeled MJs, and you'll look positively chic.
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Buy these now, and wear them forever.
It's giving Legally Blonde.
Trench Coat + T-Shirt + Jeans + Mary Jane Heels
Another classic way to style the shoes is by pairing them with your favorite jeans, T-shirt, and trench coat. This seasonless outfit idea proves once again that this style is a sound investment.
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No matter what type of shoes you buy, this T-shirt will match perfectly.
I'm a sucker for crinkled leather.
Blazer + Pajama Set + Handbag + Mary Jane Shoes
The beauty of this style is that it can make any piece in your wardrobe feel special—pajamas included. For those days you can't even be bothered to put on jeans, style a pair of matching silk pajamas with a blazer and a pair of Mary Jane shoes. It's an effortless ensemble that screams, "I woke up like this."
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The only things that can get me out of bed are coffee and sparkly shoes.
Lace-adorned pajamas are always a good idea.
Knit Crop Top and Matching Midi Skirt + Mary Jane Heels
If the idea of wearing pajamas outside the home made you shudder but you still want an outfit on the cozier side, then consider this the perfect look. What's excellent about opting for a matching knit set is that it's got the same ease as nightwear, but it's a bit more formal and ideal for transitional weather.
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Don't forget to buy the matching top.
These are the ideal hybrid of slingbacks and Mary Janes.
Statement Coat + Shoulder Bag + Mary Jane Heels
One of the best things about this shoe style is that it transitions from season to season seamlessly. You can pair it with a dress in the summer or with a statement coat and shoulder bag in the fall, and it's just as posh. The key is to invest in a fun pair of MJs that you'll want to wear year-round.
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Silver shoes? Sign me up.
Ideal for the fall.
Shearling Coat + Turtleneck + Jeans + Low-Heeled Mary Janes
Just a little reminder that these shoe aren't just for the warmer months. You can also wear this style well into the winter. Simply pair it with a great pair of jeans, a turtleneck, and a shearling coat, and you'll be able to wear this beloved style even when the temperature drops.
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Having a great pair of jeans is half the battle in styling these shoes right.
You can also style these shoes with trousers and a turtleneck for an office-friendly look.
Blazer + Shorts + Mary Jane Heels
Is winter too far off in your mind right now? Well, see this outfit as further proof that this style works year-round. Whether it's summer, fall, or spring, this no-frills suit outfit further proves that this shoe style is an investment in your forever wardrobe.
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How cute are these?
I'm not normally a shorts person, but this pair convinced me to convert.
Bucket Hat + Polo + Trousers + Mary Jane Heels
Just because this shoe style is a bit more minimalistic doesn't mean it can't pack a punch. One styling tip I swear by is pairing a monochrome look with Mary Janes in a contrasting hue. Whether you opt for a navy bucket hat, polo, and trousers like above or wear your favorite color, it's a surefire way to make these shoes stand out.
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Peak summer energy.
These shoes are sure to match any color you pair them with.
Leather Minidress + Shoulder Bag + Mary Jane Heels
Finally, I can't think of a better way to conclude my argument that this shoe is worth investing in than with the following 'fit. A little leather dress paired with Mary Jane heels? It doesn't get more adorable than this, my friends. And if this outfit doesn't sell you on this shoe style, then nothing will.
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You'll wear this dress just as much as you'll wear your new MJs.
These are worth every penny.
This post was originally published at an earlier date and has since been updated.
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