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.
-
I Called the Cuffed Jeans Trend—7 Shoes Fashion People Are Wearing With the Chic Denim Style
Style the jeans like a fashion person.
By Jennifer Camp Forbes
-
I Hate Ballet Flats But Love These Elegant Anti-Heel Alternatives
All the elevation with none of the pain.
By Eliza Huber
-
Just a Comprehensive List of All the Trending Sneakers You Need to Know About (That Aren't Sambas)
From Dries to New Balance.
By Yusra Siddiqui
-
The "Wrong Shoe Theory" Has Gone Feral in NYC—and It's Actually Working
Unexpected but so stylish.
By Michelle Scanga
-
Every Stylish Parisian Is Wearing These 6 Shoe Trends This Spring
From woven sandals to retro suede sneakers.
By Judith Jones
-
Move Over, Loafers—10 Stylish Ways to Wear Spring's Most Elegant Shoe Trend
Approved by The Row.
By Ana Escalante
-
These Are the 2025 Versions of Every Type of Shoes Your Wardrobe Needs
Your next pair incoming.
By Allyson Payer
-
If The Row, Khaite, and Toteme Feel Too Expensive, Here Are 33 Pieces to Try Instead
Bring on the luxe-looking outfits.
By Jennifer Camp Forbes