How To Pull Off Mary-Jane Flats Without Going Twee

In late 2021, TikTok fashion trend analyst and writer Mandy Lee (@oldloserinbrooklyn) sparked a hot debate: Will the Twee aesthetic from the late 2000s make a comeback? The seemingly noncontroversial question posed in her 36-second video that referenced influences like hipster style, indie music and film, and celebrity icons of the time (Alexa Chung, Zooey Deschanel, and Tavi Gevinson) spurred a strong reaction on both sides of the spectrum. One of Lee’s main explanations for why this look may be on the horizon once again is its subtle presence on recent runways — Mary Jane flats, amongst other pieces like pleated skirts and Peter Pan collars, have popped up in several collections. And despite the fact that when worn in a nostalgic, Mod-inspired way they can be quite cute, if you’re simply not a part of #TeamTwee, there are myriad ways to modernize this footwear silhouette.

“You can wear Mary Jane flats with absolutely everything,” Le Monde Beryl Co-founder Lily Atherton Hanbury says. Her design ethos when it comes to this classic shoe is to approach the look with a sense of experimentation. “We’re always playing with the high and low, traditional and modern, ornamental yet functional. For example, we developed a Georgian paste-inspired buckle and also have a plain buckle that reminds me of the ring pull on a Coke can.”

Spring and summer arrivals have already nodded at the Mary Jane flat as a trend on the rise. Brands like Dior, Mansur Gavriel, Brother Vellies, Aeyde, and The Row all have their interpretation of the shoe, with unique riffs ranging from powdery color palettes to bejeweled buckles. On the runways, Chopova Lowena introduced an edgy take with silver chains wrapping around the shoe, accented by pink charms, providing a stark departure from the Mary Jane’s Twee-adjacent spirit.

It should come as little surprise that the footwear trend has already trickled into the street style and influencer circuit, with tastemakers like Kaia Gerber and Zoë Kravitz proving that a pair of Mary Jane flats does not immediately equate to Twee, Mod, or even nostalgic style (more on that ahead). Most recently, Taylor Swift made her first public appearance after her reported breakup wearing a pair of heeled Mary Janes in a chic, New York style. As it goes with personal style generally speaking — everything is personal, so if you’re curious on how you can pull off these flats in a modern way, continue below for five standout examples.

Worn With An Edge

Starting with the shoes, Margaux Co-founder Alexandra Buckley says, “a great pair of Mary Janes has a tapered toe, a shelled-out pattern to show a bit of toe cleavage, and a smartly engineered strap over the foot for all-day comfort.” Once you’ve found the right pair for your feet, try styling them with something unexpected, like a graphic t-shirt and a leather or satin slip skirt. Layer a bold jacket on top and accessorize with an edgy handbag and ‘70s-inspired sunglasses to complete the look.

Relaxed Weekend

For an effortlessly cool, casual weekend outfit, Hanbury points to the right pair of pants. “For a contemporary take, style them with a pair of high-waisted, wide-leg jeans,” she says. To finish the look, layer in a printed T-shirt and accessorize with a headscarf and Mary Jane flats. The combination feels slightly androgynous with its mix of traditionally feminine and masculine elements, and would translate well to an afternoon picnic.

Complement A Statement Dress

There are few greater investments than an easy-to-throw-on statement dress, and Margaux Co-founder Sarah Pierson points to Mary Jane flats as “the perfect pairing with a breezy printed dress.” And with spring in full bloom, it’s the perfect time to slip into a patterned frock and accessorize with this unique footwear staple. For a refined finish, add in a few pieces of delicate jewelry.

A Bit Sporty

You may not associate the Mary Jane shoe silhouette with the sporty category, but when executed well, the result can be a slam dunk. “I actually love pairing them with shorts and a casual T-shirt,” Buckley says. To get the look, wear a windbreaker with a striped-tee and laid-back shorts to build an athleisure base and finish off with bold sunglasses and Mary Jane flats to cement the mood.

Perfect With Blue Jeans

It should come as no great surprise that Mary Jane flats are a perfect pairing with classic blue jeans. “Casual jeans and a colorful blouse worn with Mary Jane flats is the perfect look for a night out to dinner,” Buckley says. Now that you’re transitioning out of coat weather, wear a statement top and denim with a printed handbag and MJ’s for a look that could work for date night and brunch with friends.