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.
-
No Joke: Kate Middleton's Favorite Sneaker Brand Is on Sale for Amazon Prime Day
These shoes are bound to sell out.
-
I Stopped Someone in Erewhon to Ask What Shoes They Had On—Now I Can't Stop Wearing Them
They cost less than my groceries.
-
I'm a Gen Z Shopping Editor—These Are the Coolest Pieces on Reformation, Revolve, and Shopbop RN
They're giving NYC It girl.
-
Sorry, Flats—These Anti-Trend Heels Are Every French Woman's Quiet Go-To for a Night Out in Paris
A classic choice.
-
I'm Bored With My Closet—These 33 ChicReplica Store Pieces Have the Power to Turn Things Around
Effortless and expensive looking is the vibe.
-
Addison Rae, Olivia Rodrigo, and I All Cosign These Trending $30 Sandals
They're a dorm bathroom classic.
-
Don't Pack Up Your Sweaters Just Yet—Cool Fashion People Are Repurposing Them in the Chicest Way for Summer
All the outfit inspiration is inside.
-
Brace Yourself—This "Ugly" '90s Sandal Trend Jennifer Aniston Used to Wear Nonstop Is Officially Back
It's about time, if you ask me.