27 Ways to Style Mary Janes

Mary Janes elevate a wide range of looks to new levels of polish and elegance.

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Despite their resurgence in popularity, Mary Jane shoes have been a staple for centuries—a testament to their enduring appeal. The style's origin is not attributed to a single designer but, rather, evolved over many years—maturing from a little girl's shoe to a chic silhouette worn by women of all ages. Traditionally characterized by a low heel, closed toe, and a single strap across the instep, today’s Mary Janes come in various designs, materials, heel heights and price points. From ballet flats to pointed toes, block heels or platforms, these classic shoes can be dressed up or down, suitable for casual and formal occasions. Lest you think this shoe is limited in how it may be worn, let us reassure you: with proper styling, Mary Janes elevate a wide range of looks to new levels of polish and elegance.

Investing in a pair of Mary Jane shoes can be an excellent idea for several reasons, depending on your personal style, needs and preferences. But with an increasing number of covetable new arrivals every season, where does one begin in choosing the perfect pair? And, after you narrow down which silhouette is for you, how can you style your shoes so they're as versatile as possible? Below, we've paired our favorite Mary Janes in 27 ways. While we call out specific items from specific brands, the goal of this guide isn't to get you to purchase an entirely new wardrobe. Instead, we hope what you see below inspires you to pair the basics you already own in adventurous new ways. If you do need to refresh your closet, we've selected pieces in price points ranging from moderate ($$) to all-out splurge ($$$$).

Chanel Mary Jane Ballet Flats

Chanel ballerina flats are best sellers for a good reason. With their timeless design and superior craftsmanship, these shoes are forever. So, it makes sense that the iconic fashion house updated its original ballet flat with a Mary Jane strap. The Mary Jane style has two options: pink velvet with black patent leather calfskin tips or gold and black fabric. While the pink velvet is decidedly more interesting, the nature of the fabric means it will have less longevity than the gold and black versions. It is important to note that Chanel sizing can be tricky; they fit best on a narrow foot, and it’s always best to half-size up. Though adjustable, the ankle strap may limit the design to smaller-boned ones. Should you choose to invest in these (or any) Chanel ballet flats, do yourself a favor and have your cobbler add metal tips before wearing them—ensuring the lifespan of your purchase.


Pink Velvet Chanel Mary Janes: Look 1

Pair Chanel’s pink velvet Mary Jane ballet flats with classic flared pants, like these vegan leather trousers from Woldford—perfect from day to night—and a relaxed-fit, rib-knit cashmere turtleneck from ALLUDE, tucked half in, with the sleeves rolled up. Accessorize with The Row’s N/S Park tote in soft, supple, nubuck leather and round HARTANA sunnies. Finish the look with Wolford’s sheer, floral Doralee socks.


Pink Velvet Chanel Mary Janes: Look 2

Reformation’s Mason Cropped Pants in black or ‘oyster’ are another excellent option with this shoe, especially when worn with Skims’ long-sleeve crewneck bodysuit (try the ‘bronze’ version) to offset the oversized silhouette of the pant. Layer Alex Mill’s Taylor Striped Cardigan in Cotton Cashmere over the bodysuit, with the cardigan sleeves rolled up twice to show the colorful sleeves of the bodysuit. If The Row’s N/S Park tote is out of budget, consider Cuyana’s System Tote—at one-third the cost—a high-quality handbag you’ll always use and have forever. Finish the look with Isabel Marant’s Lecce Leather Belt and simple gold studs.


Pink Velvet Chanel Mary Janes: Look 3

Dress things up with this Akris sequin pencil skirt in silver (‘light melange’) or pink (‘lily’). Whichever color you choose, keep things monotone: pair Dries Van Noten’s sheer silk button-down in grey with the silver sequin skirt. If you choose the pink sequin skirt, go for the brown version of the shirt (which is truly a more burnt orange/rust shade than brown). Both tops look chic with a solid black triangle bra beneath and Akris’ reversible shearling coat in bold crimson on top. Accessorize with a sculptural black clutch like this asymmetric design from The Attico, black Wolford tights, and minimal jewelry (Dorsey’s simple yet elegant Kate rivière necklace).


Pink Velvet Chanel Mary Janes: Look 4

Veronica Beard’s Brent embellished a-line skirt isn’t just a fraction of the price of the sequin Akris option—it’s potentially more versatile thanks to its checked sequin fabric in a range of metallic pastels. Pair it with Wolford’s London Effect bodysuit (mentioned several times throughout this article because it’s a staple in many client wardrobes). Layer Anine Bing’s Ramona Sweatshirt featuring a screenprint of the iconic Kate Moss; the dropped sleeves and slightly oversized fit balance the glam of the sequins. For an even more layered look, try Zara’s pocketed flowy bomber jacket in the sweetest shade of pink (almost neutral). Simple gold studs and Reformation’s slouchy leather Vittoria Tote complete the look.


Gold Fabric Chanel Mary Janes: Look 1

  • Luxury Casual

Pair Chanel’s gold fabric Mary Janes with a mid-rise carpenter jean like this vintage-inspired design from Nili Lotan, made from non-stretch Japanese denim (hemmed to mid-ankle). On top, opt for a classic white button-down. Wolford’s London Effect bodysuit is a must-have for those who don’t care to fuss with tucking their shirts in all day long. TOTEME’s Army green, wool-blend draped fringe jacket, which features a built-in scarf, among other detailing, is an excellent layer to polish off the look—make sure to roll the sleeves up a little to balance out the bulk. Don’t be afraid to go a little monochrome with your accessories. JW Anderson’s chain-embellished shoulder bag in a similar shade of green as the TOTEME jacket keeps the look interesting. Other accessories worth considering include JW Anderson’s textured Italian leather belt with gold hardware and Dorsey’s white sapphire baguette-cut choker, worn over or under the collar of your white button-down shirt.


Gold Fabric Chanel Mary Janes: Look 2

Free People’s Moxie Barrel pull-on jean (yes, you read that right) is an excellent alternative to the Nili Lotan denim suggested above. At one-third the price, the Free People version gives the same distressed, vintage feel needed to offset the otherwise prim look of a Chanel Mary Jane. Add Barbour’s classic Beadnell jacket (the ‘Bark’ shade is great) and balance the oversized, unisex feel of the jacket and jeans with Alex Mill’s Easy Ruffle Shirt in Paper Poplin—making sure the shirt’s collar and cuffs are visible, of course. Keep jewelry minimal. A simple gold chain or small slim hoops do the trick. Layer a pair of Wolford tights beneath the jeans if it's chilly. Carry the Cuyana system tote in black croc.


Gold Fabric Chanel Mary Janes: Look 3

You don’t need to be tall or skinny to pair a flat shoe with a long dress—you just need to make sure the hem hits your mid-ankle so the entire shoe is visible—and you don’t need to fear going bold. Akris’ silk crêpe gown is an investment piece, and if you go with this or a similar style, you want to remember that less is more for everything else. Tights are optional (Wolford is always a safe bet, and these thigh-highs add an element of surprise given the dress’ high slit). If you need to bring a coat, opt for a slim-fit and cropped style, like Joseph Alloway’s reversible shearling and leather coat. Throw your phone and keys into a small leather clutch like Bottega Veneta’s ‘The Pouch,’ and remain minimalist with jewelry (simple gold studs or an understated cocktail ring). 


Gold Fabric Chanel Mary Janes: Look 4

If you don’t want to spend thousands on a dress or prefer a quieter look, Eterne’s long-sleeve turtleneck maxi dress is a great staple (also available in a mini version). Whether you opt for the mini or maxi, it is important to note that each color of the Eterne dress has a slightly different fabric texture; all are stunning, but the brown version is softer than the beige, for example. Either length looks great with Eterne’s shrunken raglan sweatshirt layered over the top (ideally in the same color for a monochrome look). Similarly, suppose Joseph Alloway’s bright orange shearling leather jacket is too expensive or loud for your tastes. In that case, Milly sells a less expensive, more neutral coat (bonus: it’s made from recycled material). Add a pop of color with Elodie’s crossbody handbag.


Manolo Blahnik's 'Campari' Pointed-Toe Mary Jane Flats

Manolo Blahnik’s pointed-toe Mary Jane flats are the epitome of sophistication in footwear design. Crafted with meticulous attention to detail, these Mary Jane flats blend classic femininity with contemporary edge. They exude understated glamor, whether you pair them with tailored trousers for a polished office look or a flowy dress for a more casual outing. 


Manolo Blahnik's Pointed-Toe Mary Jane Flats: Look 1

Play up the polka-dots in Manolo Blahnik’s Campari flocked mesh Mary Jane flats with Gucci’s checked wool-blend tweed jacket. Sure, the classic Gucci ‘GG’ pattern is a statement, but when paired with understated, straight-legged denim and a basic turtleneck bodysuit, the look isn’t so loud as it is interesting. Bottega Veneta’s ‘Mini Wallace’ bag adds another layer of texture with its signature woven leather technique. If you choose just one statement piece, you can go bold with jewelry, like Dale Hernsdorf’s Cresent Moon Bracelet featuring bezel-set garnets and diamonds.


Manolo Blahnik's Pointed-Toe Mary Jane Flats: Look 2

For a less-expensive version of the first Manolo look, pair Alex Mill’s Minnie Cardigan in Extrafine Merino Wool with Reformation’s high-rise straight jeans (fitted throughout to offset the bulk of the cardigan). Layer a Skims cotton jersey long-sleeve tee and accessorize with a black, semi-patent leather belt. Keep everything else simple: pave huggie earrings and a cocktail ring will do.


Manolo Blahnik's Pointed-Toe Mary Jane Flats: Look 3

Just because the Manolo Mary Jane is mesh doesn’t mean it’s limited to daytime. For a night out, go full-force with the polka-dot pattern by pairing this shoe with a strapless minidress like Balmain’s version, embellished with glittering black sequins and oversized crystals. Choose a fully opaque, black tight like this one from Wolford or a black crystal ankle sock like the ones offered by Cynthia Rowley. Continue the theme with Alexander Wang’s mini crystal-embellished satin tote bag. If you’re out until dawn (to be expected with such an ensemble), don’t forget to pack a pair of crystal-embellished cat-eye sunglasses.


Manolo Blahnik's Pointed-Toe Mary Jane Flats: Look 4

It must be said: Nothing can replace the above Balmain mini dress. With that, Reformation's sequin Nadine dress is a fun alternative, with a straight neckline and spaghetti straps evoking a full-on 90s vibe. As mentioned before, we encourage playing up the polka dots, this time with a sheer patterned tight. Take a trip to Zara for the brand's felt-textured coat (which also comes in black) and their silver metallic box bag (also in gold).


Roger Vivier's Chunky-Heeled Mary Jane

Roger Vivier is synonymous with timeless elegance and innovative design in luxury fashion. While primarily known for their classic stilettos, Roger Vivier’s Chunky-Heeled Mary Jane should not be slept on. These Mary Janes marry sophistication and a modern twist with a chunky heel that provides a comfortable lift while adding a bold edge to this iconic style. We've styled both the black patent and silver versions of this shoe, because we love it that much. 


Roger Vivier's Silver Chunky-Heeled Mary Jane: Look 1

Over the past few years, many have favored quiet luxury for its focus on refined sophistication. If that’s the look you’re tgoing for, start with the ME+EM tapered cargo pants and roll the cuffs to mid-ankle so they can go perfectly with flats or heels. Since these pants are wool-blend, don’t be afraid to wear them during the fall. Then, pair them with a RE/DONE stretch cotton jersey bodysuit for a comfortable, classic base. If the temperatures are particularly low, the ME+EM Metallic Bouclé Bomber jacket is a versatile piece that would complement this look effortlessly—and all the other looks on this list. Then, accessorize with Balenciaga’s silver hoops and a Kwit sterling silver black enamel pinky ring for a subtle edge. To finish off, a Loewe flamenco leather clutch bag and a Kwit emerald-cut pendant necklace would provide a practical yet refined accessory. 


Roger Vivier's Silver Chunky-Heeled Mary Jane: Look 2

Don’t think that just because it’s Vivier, it wouldn’t look good in a more casual outfit. If you want a more relaxed look, start with a classic pair of grey straight-leg jeans and a white fitted, washed t-shirt from Zara. If you want to carry a bag that fits everything for running errands but is still sophisticated enough that you don’t actually look like you’re having a busy day, pair the outfit with Cuyana’s System Tote bag. Then, to complete your look with an elegant touch, finish off with a black, semi-patent leather belt and a simple gold chain or small slim hoops. 


Roger Vivier's Silver Chunky-Heeled Mary Jane: Look 3

Never fear mixing metals—whether those tones appear in jewelry, clothing or accessories. Pair Roger Vivier's Trés Vivier Strass Buckle Babies Pumps with a simple base item of apparel, like Nili Lotan's cami gown in black (hemmed to mid-ankle). Then layer a statement piece, like this silver metallic Morrocan leather trench, which happens to be from the same designer. An ultra-shiny, sculptural gold clutch from Cult Gaia is an unexpected yet refined choice—as are the satin-finished gold and diamond stacked rings and hoops from Dale Hernsdorf.


Roger Vivier's Silver Chunky-Heeled Mary Jane: Look 4

Quince makes an incredibly versatile slip-dress in washable stretch silk that can be layered in cooler months with Skims' long-sleeve bodysuit turtleneck. The same Zara felt-textured coat that appeared earlier in this article is included (again, also available in black) due to the wildly accessible price point and clean, flattering silhouette. Add a bit of playfulness with Cuyana's mini bow bag, but keep your jewelry simple.


Roger Vivier's Black Chunky-Heeled Mary Jane: Look 1

For a more straightforward, sophisticated look, start with a Recycled Cashmere Rib Layering Sweater and a Merino Cashmere Crop Cardigan, paired with a Merino Cashmere Rib A-Line Skirt from ME + EM for a comfortable yet luxurious base. To add an artistic layer, top off the look with the Belted faux pearl-embellished topstitched denim coat from Mother of Pearl. Then, accessorize with a Shearling-trimmed textured leather shoulder bag from Brunello Cucinelli. Finally, the focal point will, of course, be Roger Vivier's Très Vivier crystal-embellished patent-leather Mary Jane pumps.


Roger Vivier's Black Chunky-Heeled Mary Jane: Look 2

This ensemble epitomizes a blend of luxury and refinement. Start with a pleated recycled-twill maxi skirt from Stella McCartney, paired with a TOTEME Paneled shearling jacket for added warmth. Then, to accessorize, wear the ISABEL MARANT Crystal-embellished silver-tone necklace for a touch of opulence and the LORO PIANA Eolian mini leather-trimmed woven cotton tote for a practical yet sophisticated accent. Then, cinch the outfit with a black semi-patent leather belt from Moore. Finally, before finishing the look with the Roger Vivier Black Chunky-Heeled Mary Jane, opt for a subtle glimmer and unique texture with the Wolford STARDUST SOCKS.


Miu Miu's Chunky-Heeled Mary Jane

Miu Miu, the avant-garde sister brand of Prada, is synonymous with daring, unconventional fashion, and its Chunky-Heeled Mary Jane is no exception. This iconic shoe embodies a fusion of retro charm and contemporary flair, with its chunky heel providing both style and stability. The Mary Jane strap, a hallmark of the design, adds a touch of playful sophistication. This pair is a testament to Miu Miu’s bold approach to fashion, redefining classic styles with a modern, audacious twist, and remains a coveted choice for those seeking a statement piece in their shoe collection. 

Miu Miu

Miu Miu's Chunky-Heeled Mary Jane: Look 1

Casual doesn’t have to mean basic or boring. This outfit seamlessly blends a luxurious approach to casual dressing, starting with a color-blocked cashmere cardigan from Marni, paired with the Pleats Please pants in dark green from Issey Miyake. To give the look a bit of a textural contrast, pair Miu Miu’s Chunky-Heeled Mary Janes with shiny grid socks from Wolford. To top off the look during the winter, the Loro Piana leather-trimmed cashmere coat is a good option, as it exudes elegance while providing warmth. Then, accessorize with the Alaïa Khaima small leather tote and a pair of cat-eye sunglasses from Bottega Veneta for a hint of vintage charm. For a touch of opulence, add the Kwit emerald pendant necklace


Miu Miu's Chunky-Heeled Mary Jane: Look 2

This look embodies casual chic with a touch of refinement, centered around Miu Miu’s Chunky-Heeled Mary Janes. The Reformation Cynthia high-rise straight jeans in Vintage Marzipan provide a classic and flattering base, while the Good American funnel neck long-sleeve bodysuit adds warmth and style. The Reformation cropped cashmere turtleneck in Merlot also brings a luxurious touch to the look. Cinch the outfit with a black, semi-patent leather belt and a silver metallic box bag from Zara to complete the ensemble with a defined, modern element, blending comfort with sophistication. 


Miu Miu's Chunky-Heeled Mary Jane: Look 3

This ensemble exudes opulent refinement for a luxurious formal occasion. The LA Double J sequined swing maxi dress is a head-turner for its intricate detailing and graceful silhouette. Meanwhile, the Clio Peppiatt bead-embellished satin shoulder bag adds an artistic touch, featuring recycled acrylic beads that reflect light like glistening water droplets. Plus, it’s made from soft satin, making it light and easy to carry around. Complete the look with the one-of-a-kind Dale Hernsdorf suspension earrings with opals. Each opal was sourced individually, showcasing multicolored Austrailian boulder opals suspended from diamond studs by a handmade chain, all set in matte satin-finished 22K yellow gold. Truly, this would elevate your look to an extraordinary level of luxury and sophistication.  


Miu Miu's Chunky-Heeled Mary Jane: Look 4

For an understatedly glamorous look, the Reformation Kinsey Knit Dress in pink sparkle boasts a flattering, delicate shimmer, epitomizing subtle elegance, especially when paired with Miu Miu’s Chunky-Heeled Mary Janes. For a luxurious (yet affordable) finish that adds flair, pair the dress with a silver metallic box bag from Zara.


Bottega Veneta Mary Jane Wedge Pumps

Bottega Veneta's Comet Mary Jane Wedge Pumps reimagine the timeless charm of the classic Mary Jane with a modern twist. Departing from the traditional flats or standard heels, Bottega incorporates a comfortable wedge heel, revolutionizing both style and long wearability. This design not only provides a stable and comfortable lift but also adds a contemporary edge to the iconic shoe. Crafted with Bottega Veneta's renowned attention to detail and high-quality materials, these pumps seamlessly merge comfort and style, making them a versatile and chic choice for any occasion.

Bottega Veneta

Bottega Veneta Mary Jane Wedge Pumps: Look 1

This look is a blend of classic and modern luxury. Start with the Colorado Thong Bodysuit from Wolford, which has a subtle shimmery touch, paired with birch trousers. Then, to add a unique, artistic touch, finish the base with the Dries Van Noten Veston floral-print quilted shell jacket. Paired with the Bottega Veneta Andiamo medium intrecciato leather tote, this outfit balances practicality and high-end design. Complementing this, the D.M.J. custom lab-grown diamond ring and emerald crystal necklace from Dorsey bring a subtle touch of glamor. Together with the Bottega Veneta Comet Mary Jane Wedge Pumps, these carefully curated pieces create an understated yet luxurious appeal.


Bottega Veneta Mary Jane Wedge Pumps: Look 2

This look is a testament to elegance and thoughtful design. Stat off the look with the Neon 40 tights from Wolford and the silk-organza Bellamy dress from Khaite for a graceful, ethereal charm. Then, pair the ensemble with the Max Mara reversible shearling coat for added warmth, especially as the temperature drops. Finally, accessorize with the Benedetta Bruzziches Venus La Petite crystal-embellished satin clutch and Bottega Veneta Comet Mary Jane Wedge Pumps for a cohesive, elegant look that is wearable to any occasion.


Bottega Veneta Mary Jane Wedge Pumps: Look 3

Effortlessly combining comfort with a touch of understated gracefulness, this ensemble exudes a relaxed yet polished charm. For the base, start with a classic crew neck tee and the Mason pant from Reformation, layered with a cotton polo sweater from Alex Mill for a laid-back appeal. The Zara hooded coat would provide a stylish yet cozy layer, while the Madewell leather western belt gains a touch of rustic flair. Plus, the Cuyana system tote, along with simple gold chain and small slim hoops add a subtle hint of sophistication. Of course, the Bottega Veneta Comet Mary Jane Wedge Pumps is the focal point of the look, adding a modern twist to this otherwise timeless look.


Bottega Veneta Mary Jane Wedge Pumps: Look 4

This night-time look is a captivating blend of glamor and sophistication. The Reformation Maves dress is a particular showstopper, with its sleek design and luxurious silk fabric, perfect for a night out on the town. The dress is best complemented with Wolford sheer tights, providing a more feminine touch. Additionally, the Reformation cropped jacket adds a chic layer, while the slouchy leather Vittoria Tote, also from Reformation, adds a simple yet luxurious touch that perfectly matches the Bottega Veneta Comet Mary Jane Wedge Pumps. Completing the look, the pave huggie earrings from Studs add a hint of sparkle.


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