Step Aside, Sneakers—I'm Wearing This Pretty Shoe Combo All Winter

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Woman wears black patent Mary Janes, sheer socks, and blue jeans.

(Image credit: @annelauremais)

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.

Woman wearing black coat, black Mary Jane shoes with socks, and black handbag standing on a street in Paris.

(Image credit: @nlmarilyn)

Woman wearing a brown minidress coat, black Mary Jane shoes with white knee-high socks, and black heart-shaped handbag standing on a street in New York.

(Image credit: @alyssainthecity)

Woman wearing a striped coat, navy sweater, gray skirt black Mary Jane shoes with socks, and yellow handbag standing on a street in Paris.

(Image credit: @emanuellek_)

Woman wearing mid-wash jeans and black Mary Jane shoes with sheer socks.

(Image credit: @annelauremais)

Woman wearing white dress, black Mary Jane shoes with white socks, and black handbag standing on a street in New York.

(Image credit: @lefevrediary)

Woman wearing blue denim shorts, black Mary Jane shoes with sheer black knee-high socks, and pink handbag standing on a street in New York.

(Image credit: @aishafarida)
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Ana Escalante
Ana Escalante
Associate Features Editor

Ana Escalante is an award-winning journalist and Gen Z editor known for her sharp takes on fashion and culture. She’s covered everything from Copenhagen Fashion Week to Roe v. Wade protests as the Editorial Assistant at Glamour after earning her journalism degree at the University of Florida in 2021. At Who What Wear, Ana mixes wit with unapologetic commentary in long-form fashion and beauty content, creating pieces that resonate with a digital-first generation. If it’s smart, snarky, and unexpected, chances are her name’s on it.

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