Modernize Your Mary Jane Shoes with These 14 Outfit Ideas

So many new ways to wear the classic style.

Mary Jane Shoes Outfits Classic

Design by Tiana Crispino

Mary Janes are one of the few shoes that grow with us as we go through our fashion journey. From the shiny black pair many of us wore to special events as children to the stylish pump version that's a top choice for job interviews today, they seem to always have a place when we're trying to look put together. And thanks to the revival of '90s and '00s fashion trends, Mary Jane shoes are coming back into popularity with more variety than ever. Heeled, flat, multi-colored, and multi-strapped—with all these choices, it may be hard to decide just which pair of Mary Janes to try first.

Luckily, we’re here to help. Ahead, see 14 easy ways to wear Mary Janes—whether you’re going for a Blair Waldorf-inspired look or a dark academia vibe, we've got you covered.

The Classic 

Mary Jane Shoes Outfits Classic

Design by Tiana Crispino

Mary Janes have always had a vintage “goody two-shoes” vibe about them. If you're going for the classic vibe, pair a flat style with a collared dress and some ruffled socks.

The Blair Waldorf 

Mary Jane Shoes Outfits Blair Waldorf

Design by Tiana Crispino

My personal style icon, Blair Waldorf's creative school uniform looks had such a hold on our wardrobes in the late aughts, making Mary Janes, headbands, and pleated skirts popular again. Channel your inner Blair with heeled Mary Janes, a navy skater skirt, a matching cardigan, and a collared shirt.

Cottagecore Chic

Mary Jane Shoes Outfits Cottagecore

Design by Tiana Crispino

Cottagecore lovers adore Mary Janes for their simplicity and casual elegance—they're the perfect choice for picnics or chilling in the garden. Pair some flat Mary Janes with a flowy puff-sleeved dress for instant style.

Pop of Color 

Mary Jane Shoes Outfits Pop of Color

Design by Tiana Crispino

Don’t limit yourself to just black Mary Janes when you can get them in all kinds of colors. Pick up a vibrant pair and wear them with an all-white outfit to make them instantly stand out, proving that these shoes are anything but boring.

Work Ready

Mary Janes Shoes Outfits Work

Design by Tiana Crispino

Mary Janes are no strangers to office life. Instead of pairing them with a dress or skirt, try a button-up silk shirt, some plaid trousers, and Mary Jane loafers to add a twist on the hyper-femme shoe.

'90s Vibes

Mary Janes Shoes Outfits '90s

Design by Tiana Crispino

Embrace your love of the '90s by adding a pair of chunky Mary Janes with a slip dress, white tee, and a matching scrunchie that will have you totally bugging in the best way.

Dark Academia 

Mary Janes Shoes Outfits Dark Academia

Design by Tiana Crispino

Mary Janes fit perfectly with the dark academia aesthetic, as it already has a boarding school vibe. Make these classic shoes fit into dark academia by pairing them with a muted color palette, a plaid skirt, and a chunky sweater. It's perfect for going to solve mysteries.

Preppy Style

Mary Jane Shoes Outfits Preppy

Design by Tiana Crispino

Mary Janes have always been associated with the preppy look. Take things to the next level with a tweed blazer and skirt set to give some major "Olivia Rodrigo at the White House" vibes.

Summer Vintage 

Mary Janes Shoes Outfits Summer Vintage

Design by Tiana Crispino

Transition your Mary Janes from winter to summer with a nice collared shirt and a pair of high-waisted shorts—it's an effortlessly cool look that you’ll be rocking all summer long.

'70s Moment

Mary Janes Shoes Outfits '70s

Design by Tiana Crispino

People have been rocking the Mary Jane look for decades, so don’t be afraid to play with different periods in your own look. Bring on the '70s with a denim jumpsuit, some silver Mary Jane heels, and a groovy bag.

Casual Cool

Mary Janes Shoes Outfits Casual Cool

Design by Tiana Crispino

Who says Mary Janes have to be polished all the time? This classic style looks just as good with a pair of jeans and a T-shirt as it does with a dress or matching set. However, if you want to add a little structure, top off your look with a nice blazer that’s casual but put together.

Running Errands

Mary Janes Shoes Outfits Errands

Design by Tiana Crispino

You don’t need to wear Mary Janes for special occasions only. Slip on your favorite pair along with a pair of white jeans and a cool bomber jacket for an easy but stylish look, so you can feel like the main character at the grocery store.

Emo Forever

Mary Janes Shoes Outfits Emo

Design by Tiana Crispino

While a preppy wardrobe staple, Mary Janes can easily go to the darker side of the fashion spectrum and be paired with some alternative looks. Pair a chunky Mary Jane, a pleated leather skirt, and a velvet turtleneck and we’re back into our emo phase.

Date Night 

Mary Janes Shoes Outfits Date Night

Design by Tiana Crispino

While Mary Janes are traditionally innocent, they can easily go from day to night with the right look. Try a heeled pair with a sweater dress and a leather jacket for a date-ready ensemble.

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