I Never Know What Shoes to Wear in the Winter—So Here Are My Top Picks
Photo Credit:@jackyinberlin
There’s something about winter that makes getting dressed feel like a group project you didn’t sign up for. Especially when it comes to shoes. Every year, I forget how hard it is to find a pair that’s stylish, warm, waterproof, and doesn’t make you sound like you’re trudging through snow in combat boots.
And if you live somewhere cold—like, actual winter cold—then you already know the drill. Cute heels? Not happening. Suede boots? Goodbye. Sneakers? Only if you enjoy frostbite. It’s a fine line between looking put together and looking like you just crawled out of a ski lodge.
After one too many slippery mornings and destroyed leather soles, I finally cracked the code. You don’t need a different pair for every temperature drop—you need situational shoes. Pairs that get the assignment without ruining the outfit.
So, here they are. My go-to winter shoes, sorted by the moments that actually happen in real life.
And if you’re ready to build a full-season wardrobe around them, start with the 365 Outfit Ideas Guide it’s like a personal stylist for your everyday life.
Need Help Finding The Perfect Shoes? Read These
I Finally Figured Out What Shoes Actually Go With Every Type of Jeans
Confused About What Jeans to Wear with Ankle Booties? Let’s Sort It Out!
1. The “I’m Late and It’s Icy” Boot
You’re already two minutes behind, the sidewalk’s an ice rink, and your Uber driver is giving up hope. This is where traction meets taste. A lug sole, a bit of height, and a silhouette that still looks sleek with trousers or leggings. It’s not the time for stilettos; it’s the time for survival—with style.
Walmart
Platform Combat Boots
$39.99
Walmart
Platform Lugsole Chelsea Boot
$29.99
2. The “Running Errands but Make It Cute” Shoe
It’s Saturday, you’ve got five stops to make, and you still want to feel like you tried. That’s where practical-cute shoes come in—low-profile sneakers or weather-resistant loafers. They’re the kind of shoes that say, “I’m productive, but I could also grab a matcha and scroll through Pinterest for an hour.”
Amazon
UGG Women's Tasman II Slipper
$124.99
The ReVelvet™ Double Bit Loafer
$169
3. The “Dinner Plans and Sub-Zero Temps” Heel
There’s no worse feeling than being bundled in your best outfit and realizing your shoes ruin everything. I’m convinced every woman in a cold city keeps a secret stash of heels that look good and can survive a cab dash. Think block heels, pointed toes, or sleek boots that peek perfectly under your jeans or dress pants.
Cosmic Pump
Tony Bianco
$170
Luca Boot
Steve Madden
$200
Greta Boot
LPA
$288
4. The “Office-to-After-Work Drinks” Boot
You know that pair that somehow looks corporate at 9 a.m. and cool at 9 p.m.? That’s the one. Leather or faux leather, structured but not stiff, with just enough polish to make you look like you didn’t change your shoes under the desk (even though you did).
Georgie Pump
Tony Bianco
$160
Amazon
Chunky Mid Heel Booties
$59.99
5. The “Travel Day but Still Stylish” Slip-On
Airport security is not the place to lace up knee-high boots. You need easy-on, easy-off shoes that still look chic in terminal lighting. I lean toward structured mules or flat boots that can handle airport miles without feeling too casual. Bonus: they double as your go-to brunch shoes once you land.
Rothys
The Puddle Skipper Boot
$229
Rothys
The Casual Clog
$159
6. The “Work-From-Home but Still Want to Feel Dressed” Flat
If you’re living in sweats (hi, same), a sleek flat or indoor-outdoor mule will convince your brain you’re doing something productive—even if you’re just moving from your desk to the couch. The secret? Pick one that feels as comfy as a slipper but looks like you could step outside and grab coffee.
Amazon
Backless Faux Fur Slides Mules
$56.99
Amazon
Studded Flats
$54.99
And if you’re ready to build a full-season wardrobe around them, start with the 365 Outfit Ideas Guide — it’s like a personal stylist for your everyday life.
Need Help Finding The Perfect Shoes? Read These
I Finally Figured Out What Shoes Actually Go With Every Type of Jeans
Confused About What Jeans to Wear with Ankle Booties? Let’s Sort It Out!
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