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

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.

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.
-
Cozy Cashmere! Sleek Suede! Dark Denim! 32 Affordable Fall Pieces You'd Find in a Wealthy Person's Closet
Oh, did I mention they're under $250?
-
This Dated Denim Pairing Is Suddenly the Chicest Way to Wear Jeans for Fall 2025
Easy and stylish.
-
I Thought I Hated Ballet Flats Until I Found This Elegant (and Blister-Proof) Pair
Now, I need it in every color.
-
Here They Are: The 6 Biggest Boot Trends of Fall 2025
Exotic finishes! Sock boots! Western motifs!
-
My Mom Only Shops Affordable Fashion—I Sent Her These 27 Chic Rich-Looking Pieces for Fall 2025
Everything is under $100.
-
Everything Who What Wear Editors Saw, Wore, Did, and Ate During NYFW
Let's dive in, shall we?
-
Paris Hilton's World: Her Pink Motorola Razr, Favorite Y2K Looks, and What 11:11 Media Means to Her
A glimpse into the life of this savvy entrepreneur.
-
After 2 Weeks in Italy, I'm Convinced I Need the Shoe Trend Every Chic Woman in Milan and Rome Was Wearing
Forget ballet flats.