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Since the beginning of their existence, Mary Janes have been celebrated for their versatility. Not only can they be worn with a professional work ensemble, but that same pair can easily turn into your go-to shoes for a night out, or even running errands on your Sunday afternoon. 

With endless Mary Jane styles, it is easy to find the perfect pair to fit your personal style. Whether your style aesthetic leans more casual, edgy, or somewhere in between, we’ll take you through how to style Mary Janes to fit your tastes.

Price Reference (Total outfit price):

$ | Under $100
$$ | Between $100-$200
$$$ | More than $200

A Casual Meets Chic Option

Overall Price: $$

Historically, Mary Janes were celebrated for their comfortable design that could be worn for hours at a time, making them the perfect option for elevating your casual ensembles. An outfit made up entirely of your closet staples, the breezy silhouette of a satin blouse creates an effortlessly chic look when styled with a pair of medium wash straight leg jeans. Complete the look by adding a cozy cardigan-style coat that’s perfect for cooler weather, and a tote bag that can be worn as a cross-body or a satchel–and of course, a pair of square toe Mary Jane shoes. 

This style, made with a glossy patent fabrication, features two sleek straps that can be adjusted to your specifications. Its low, chunky heel gives you a subtle boost in height, while maintaining comfort, making them an ideal choice for a day at the office, walking around campus, or completing errands.

An Edgy Take

Overall Price: $$

Channel a hint of childhood nostalgia with puffy dresses and patent flats in this grown-up version of your “Sunday Best.” This edgy-femme outfit is perfect for daily wear, heading to class, or meeting friends for a treat. A jet-black, tiered babydoll style dress paired with sheer black tights creates a bold pair that’s softened by the playful puffiness in the dress’ silhouette. 

A classic way of styling Mary Janes is with a pair of statement socks. This pair of socks with frilly lace trims layered over the tights and completed with Steve Madden’s super chunky Mary Janes brings the whole look together with a soft-meets-edgy appearance. 

This pair is accented with an oversized gold buckle that’s designed with a bulbous-like appearance to give the shoe more dimension. Finish the look off with a dainty gold heart-shaped necklace and an embroidered heart purse, which ties together every minor detail. Together, these closet essentials make every decision you made when selecting your outfit appear more intentional and sophisticated.

Class Is In Session

Overall Price: $$$

There’s something about a wool jacket and a pair of simple Mary Janes that instantly makes me feel more elegant. This look, inspired by my soft-side for dark academia aesthetics, combines closet staples with cozy patterns and warm colors to create a preppy look that’s perfect for heading to class or going into the office in the chilly months. 

A mock neck sweater made from the softest eyelash yarn, and a mini skirt with a small slit at the thigh, creates a neutral palette for you to get creative with your styling. For a collegiate-meets-sophisticated look, layer your outfit with a woolen pea coat adorned with a red, tan, and black plaid pattern.

A pair of classic Mary Janes in a red-tinted cognac brown will make your outfit standout on its own, but when coupled with the coordinating peacoat, you’ll look like the star of your office. Complete the look with a vintage-inspired briefcase bag that can safely transport your laptop, books, or your purse essentials.

Bold Blends With Femme

Overall Price: $$

One of my favorite ways to style Mary Janes is with a layered slip dress. The perfect outfit for date night, this ensemble includes all of our femme favorite essentials. Create a dainty look that’s equally cute and sexy by layering this blush pink maxi slip dress over the sheer crop top that’s been adorned with pearl and rhinestone accents along the bodice and sleeves. 

Elevate the look with a pair of red Mary Janes featuring a pointed toe, three adjustable buckle straps, and a sculptural heel that brings a romantic and sophisticated feel to your outfit. Although this pair has a larger heel–measuring in at 2.5-inches–you don’t have to worry about sacrificing comfort for fashion.

To complete your date night look, add a pair of bow-shaped dangle earrings and a red clutch purse to emphasize and complement the vibrant hue of your Mary Jane heels.

Boho Garden Party

Overall Price: $$$

When we say there’s a Mary Jane for every style, we mean every style. Combining vintage and bohemian influences, this look is a dreamy and breezy addition to add to your wardrobe for those warm spring and summer months. The flowy dress, made with eyelet lace at the skirt, a square neckline, and billowing balloon sleeves makes the outfit feel so whimsical and youthful, while the chunky-soled Mary Janes brings an understated finish to the look. 

This idea can be dressed up as much as you desire, so don’t leave the jewelry at home! Pair floral-accented earrings to bring out the light blue shade of the dress, and to make a square neckline appear less harsh, add a dangling charm necklace for a romantic finish. 

This outfit makes me want to traipse through the aisles at my local farmers market, so of course, don’t forget to grab your netted tote bag for a day out in the sun.

Dainty Punk Rocker

Overall Price: $$

Mary Janes are the perfect addition to the punk rocker’s closet. This outfit combines those punk rock influences with feminine details to create a striking–yet delicate–look that’s perfect for everyday or a night out at the club with your best friends.

The star of the show is obviously these platform Mary Jane heels that resemble a toned-down version of Sabrina Carpenter’s signature platform boots, but this dress is a close second. With several tulle layers that create a puffy silhouette, balloon sleeves, frilled trims, and a jersey slip lining that completes a dynamic appearance, when you combine this dress with the chunky platform Mary Jane heels, you’ll look and feel unstoppable. To emphasize the ultra-feminine details of this look, add a pair of sheer ruffled socks and accessorize your hair with a long tulle bow.

If you want to play more on the edgy punk-rocker appearance, complete your look with a pair of safety pin-inspired hoop earrings.

At The Office

Overall Price: $$$

If you’re tired of only finding boring slacks and tacky blouses when searching for office attire inspiration, look no further. Make your next day at the office your best one yet with the help of a chic outfit paired with the most comfortable pair of Mary Jane flats imaginable.

Begin planning your outfit with this pair of slim-fitted trousers that are cropped just above the ankle for a modern look. Bring comfort to your day by adding a fuzzy knit cardigan sweater–a closet staple that can be worn alone or layered–and complete the look with a lightweight plaid-printed blazer.

To elevate your office look, opt for this pair of Mary Jane ballet heels featuring a low-slung chunky heel and a duo of straps that lend a bold finish to your ensemble. This style is not only an ideal addition to your workday ensemble, but they also look good with any party fit for your future happy hours!

Eclectic Art Teacher

Overall Price: $$

We’ve seen maximalism grow into one of the largest trends of the year. This trend doesn’t just limit itself to home decor, either, it’s just as prevalent in fashion, too. This outfit includes playful pieces that bring whimsy and colorful pops into your wardrobe. The knit maxi-length skirt is so comfortable for a long day in class, while the lettuce-trimmed mock neck top brings balance to the skirt’s checkered pattern statement.

Play into the eclectic elements by adding a pair of sheer, polka-dotted socks with your Dr. Martens Mary Janes. Unlike classic Dr. Martens shoes, these Mary Janes don’t require much effort on your part to break in, making them the perfect addition for those long days of work, taking walks, and your other daily adventures.