I have a confession: I hate high heels.
Unlike the opening montage in The Devil Wears Prada, I can't imagine willingly putting on a pair of sky-high stilettos to head into the office. As a new New Yorker, I do a ton of walking—mostly in my beat-up Adidas Stan Smiths that I've practically worn down to nubs in an ode to Phoebe Philo, who would famously wear them during runway shows during her Céline tenure.
Since adopting a morning commute that involves trekking almost a mile to work, having good, comfortable footwear is my mantra. The Who What Wear team doesn't look twice at my beat-up trainers (it's a no-judgment zone!), but sometimes, I want to spice up my footwear and feel a bit fancier when heading into the office. My latest obsession? Mary Janes with socks or leg warmers for an indie look.
As I'm a child of the internet age, Tumblr is my style North Star, and there's nothing more 2014 grunge than a chunky pair of Mary Janes paired with some frilly, pretty socks. Now that twee and indie sleaze styles are having a major resurgence, it's no surprise that Mary Janes and chunky, slouchy socks are at the top of my mind.
Below, scroll through the combinations of Mary Janes and hosiery that have been living in my head rent-free.
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Better Than Ballet Flats (and Loafers): The Shoe Trend It Girls in NYC and Paris Will Be Wearing This FallThey're classic but fresh at the same time.
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Back to School: 5 Collegiate Shoe Trends That'll Be Everywhere This FallChic, comfy, and compliment-guaranteed.
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I'm an NYC Shopping Editor—I Can't Stop Thinking About These 31 Rich-Looking Fall Finds From Nordstrom, Zara, and H&MDid I mention they're under $250?
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These 32 Chic Zara Fall 2025 Shoe Finds Are the Key to Looking Like a Fashion Person—Good Luck Picking Just One PairPrepare for endless compliments.
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People With Impeccable Taste Swear By COS—21 Chic Sale Finds to Take Advantage of Right NowDid you say 25% off? Yes, please.
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I'm a Fashion Editor on a Budget—27 Incredibly Chic Fall Finds That Will Get You More Bang for Your BuckStellar under-$150 finds right this way.
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These 32 Elevated Nordstrom and Zara Finds Make Getting Ready So Much Easier (and Chicer)Here's to effortless outfits.
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Here's What to Look For If You Want Ballet Flats That Scream 2026If you haven't upgraded your ballet flats by now, wyd?
