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. TheBest Knockoff Luxury Clothing 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.
-
Fashion People in Their 20s and 50s Wear This Flat-Shoe Trend With Skirts to Look Chic
Hint: It's not loafers.
-
If You Hate Flip-Flops, Try the Viral Sandal Trend Everyone With Good Taste Is Wearing This Summer
You can trust me.
-
Brand Layering: The Art of Knowing Which Labels to Pair With Each Other
The ultimate styling hack.
-
I'm a Shopping Director—10 Shoe Silhouettes I Love RN (and How to Style Them)
Sandals, sneakers, heels, and more.
-
From A-Listers to the F1 Paddock—Inside the Meteoric Rise of 2025's It Sneakers
Let's ride.
-
The Simple Styling Trick That Turns Pencil Skirts From Corporate to Chic in 5 Seconds or Less
It's completely free and ready to copy.
-
Everyone Will Copy J.Law and Wear This "Ugly" Shoe Trend With Jeans and Trousers
Starting at just $20.
-
If You Run Into Me This Summer, There's a Good Chance I'll Be Wearing One of These 7 Incredibly Cool Sneaker Outfits
Balancing comfort and style.