Suddenly, Everyone in Fashion Is Wearing These Anti-Trend Shoes

Do you ever look at your closet and say, “I have no practical shoes to wear?” Because let me tell you, I sure have. When it comes to curating a collection of fashionable and functional footwear, it 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). You can understand then 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 style ever really went out of style, but with the focus on trendier styles (ahem, platform sandals, glass heels, and ballet flats), the Mary Jane shoe style wasn’t entirely a part of the conversation. But considering that this shoe has been spotted in recent runway collections and the fashion set has fastidiously taken up rewearing the style, it’s safe to say that this shoe is starting to get the recognition it deserves again. After all, this style is arguably one of the best shoe purchases you can make, but it also has infinite styling possibilities.

To prove my point, I’ve rounded up 15 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, because after you read this, you’ll no longer claim to have any comfy-yet-cute shoes.

White Button-Down + Denim Miniskirt + Woven Bag + Mary Jane Heels
mary jane shoe outfit ideas

Photo:

@emmanuellek_

You know a shoe style is worth giving 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.

Shop the key pieces:

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
mary jane shoe outfit ideas

Photo:

@alyssainthecity

What's so wonderful about this shoe style is that it really does all the work of elevating every look. Case in point? The outfit above. A simple tank top and pencil skirt become a look when styled with a pair of chunky MJs. 

Shop the key pieces:

A simple tank will make your shoes pop even more. 

Oversize Blazer + T-Shirt Dress + Mary Jane Flats
mary jane shoe outfit ideas

Photo:

@annelauremais

Another simple way you can incorporate mary jane shoes into your life seamlessly? Pair them with a T-shirt dress, oversize blazer, shoulder bag, and sunglasses. It's easy to throw on yet embodies that cool, French effortlessness.

Shop the key pieces:

This will match everything you already own. 

Oversize Sunglasses + Button-Down + Biker Shorts + Mary Jane Shoes
mary jane shoe outfit ideas

Photo:

@maria_bernad

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 Dorthy's red slippers, but they're magic nonetheless. 

Shop the key pieces:

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
mary jane shoe outfit ideas

Photo:

@michellaccc

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 make homage to its history than going for 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. 

Shop the key pieces:

School may be out, but these shoes are seasonless. 

Pairing a knee-high sock with your mary jane shoes is bound to secure you some compliments. 

Blazer + T-Shirt + Pleated Miniskirt + Mary Jane Flats
mary jane shoe outfit ideas

Photo:

@goodwoodx

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 feel without feeling too kitschy. 

Shop the key piece:

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
mary jane shoe outfit ideas

Photo:

@lefevrediary

PSA: Mary Jane shoes aren't just sweet little school-girl-inspired shoes. Brands across the board (from Versace to Jeffery Campbell) have taken this formerly sweet shoe into the spicy territory by adding a platform, and the fashion set is eating it up. But if you're unsure of how to make this edgier take on the shoe work, I recommend pairing a feminine 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. 

Shop the key piece:

These come in five other colors in case you're not a fan of pink. 

Statement shoes deserve to be styled with bold sunglasses. 

Peter Pan Blouse + Satin Minidress+ Printed Tights + Mary Jane Heels
mary jane shoe outfit ideas

Photo:

@shhtephs

Another unique way to style these shoes is by leaning into their inherent quirkiness. Pair them with an oversize Peter Pan blouse, satin minidress, and printed tights and you'll be wearing these shoes—not the other way around. 

Shop the key pieces:

Styling hack: You can also forgo the Peter Pan blouse and tights and throw a chunky cardigan over this dress for an equally cute way to style your MJs. 

Tweed Jacket + Tweed Dress + Layered Necklaces + Mary Jane Heels
mary jane shoe outfit ideas

Photo:

@yoyokulala

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. 

Shop the key piece:
Trench Coat + T-Shirt + Jeans + Mary Jane Heels
mary jane shoe outfit ideas

Photo:

@aida.bdji

Another classic way to style the shoes is by pairing it with your favorite jeans, T-shirt, and trench coat. This seasonless outfit idea proves once again that this style is a sound investment. 

Shop the key piece:

No matter what type of shoes you buy, this T-shirt will match perfectly. 

Blazer + Pajama Set + Handbag + Mary Jane Shoes
mary jane shoe outfit ideas

Photo:

@daleedasoomar

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 pair of Mary Jane shoes. It's an effortless ensemble that screams, "I woke up like this." 

Shop the key pieces:

The only thing that can get me out of bed is the idea of coffee or sparkly shoes. 

Pink pajamas are always a good idea. 

Knit Crop Top and Matching Midi Skirt + Mary Jane Heels
mary jane shoe outfit ideas

Photo:

@anaasaber

If the idea of wearing pajamas outside the home made you shudder but you still want an outfit idea 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 is ideal for transitional weather. 

These are the ideal hybrid between slingbacks and Mary Janes. 

Statement Coat + Shoulder Bag + Mary Jane Heels
mary jane shoe outfit ideas

Photo:

@gosiaboy

One of the best things about this shoe style is that it lends itself well to transitioning from season to season seamlessly. You can pair it with a dress in the summer, or in the fall, you can pair it with a statement coat and shoulder bag, 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. 

Shop the key piece:

Leave it to Miu Miu to make the most magical shoes I've ever seen. 

Coat + Turtleneck +Jeans + Low-Heeled Mary Janes
mary jane shoe outfit ideas

Photo:

@venswifestyle

Just a little reminder that this shoe isn't just for the warmer months. In fact, you can 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. 

Shop the key piece:

Having a great pair of jeans is half the battle in styling this shoe right. 

You can also style these shoes with trousers and a turtleneck for an office-friendly look. 

Blazer + Shorts + Mary Jane Heels
mary jane shoe outfit ideas

Photo:

@fridabecker

Is winter too far off a concept 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. 

Shop the key piece:

I'm not normally a shorts person, but this pair convinced me to convert to the cause. 

Bucket Hat + Polo + Trousers + Mary Jane Heels
mary jane shoe outfit ideas

Photo:

@vikilefevre

Just because this shoe style is a bit more minimalist in nature doesn't mean it can't pack a punch. One styling tip we swear by is pairing a monochrome look with Mary Janes in a contrasting hue. Whether you opt for a navy blue bucket hat, polo, and trousers like above, or wear your favorite color, it's a surefire way to make this shoe stand out. 

These shoes are sure to match any color you pair them with. 

Leather Minidress + Shoulder Bag + Mary Jane Heels
mary jane shoe outfit ideas

Photo:

@melodiebance

Finally, I can't think of a better way to conclude my argument that this shoe is worth investing in than 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. 

Shop the key pieces:

You'll wear this dress just as much as you'll wear your new MJs. 

Related Stories