7 Cool (and Warm) Winter Outfits to Wear With Flats

Unlike summer when you choose to spend as much extra time outside as you can and opt to walk instead of grabbing that six-minute Uber, winter is a good excuse to be on your feet a little less and, thus, break out the heels a little more. However, there’s value in relying on cold-weather looks that skip the stilettos in favor of shoes that are comfortable, practical, and close to the ground. We’re talking winter outfits with flats, of all varieties and styles.
The options for flat winter shoes run the gamut. There’s a classic ballet option, of course, and in case you need a bit more coverage, sneakers, lug-sole boots, and lace-up Dr. Martens do the trick. And to demonstrate exactly how to compile seasonally on-point looks that don’t skimp on comfort, warmth, or creative styling, the seven looks below serve as examples. Read on for tips to re-create, and to shop all the necessary pieces.
Slip-on sneakers are some of the easiest flat shoes to wear with any chilly-weather ensemble. We like this version that mixes neutral tones in a variety of cozy textures.
Shop similar styles:
Iconic Timberland boots complete this outdoorsy winter look, especially when paired with dark denim and a layer of Patagonia.
Shop similar styles:
If you stick with ballet flats, may we suggest something with some shine? It'll make any jeans-and-chunky-sweater ensemble extra special.
Shop similar styles:
Opt for an itty bit of flatform via Dr. Martens to achieve this polished yet comfortable ensemble that's perfect for any day at the office.
While we've seen several Kardashian sisters wearing heels with their athleisure in the winter, we suggest breaking out your favorite coordinating sneakers instead.
Shop similar styles:
Yes, hiking boots are a quite popular option for flat shoes in the winter. And we suggest elevating the look by pairing them with your fuzziest, and most statement-making, coat.
Shop similar styles:
Crisp white sneakers are an all-weather necessity. For this season, simply pile on all the long layers and toasty accessories and go.
Shop similar styles:
Next, plan the perfect holiday look while sticking to your simple sense of style.

Who's your style icon?
Taylor Tomasi Hill
Who are your 5 favorite people to follow on Twitter/Instagram?
@tamumcpherson @lisasaysgah @therealgracecoddington @everyoutfitonsatc @notmynonni
What's the fashion essential you can’t live without?
A leather jacket.
What's your desert island album?
Beyoncé "B'Day." Or pretty much anything Beyoncé.
-
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?
-
Dark-Blue Jeans Are Definitely "In" for Fall 2025, But so Is This Other Elegant Denim Wash
Trust us you'll want to include it in your cold-weather wardrobe.
-
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.
-
EverythingBest Knockoff Luxury Clothing Editors Saw, Wore, Did, and Ate During NYFW
Let's dive in, shall we?
-
Loafers Are Great, But If You're Bored, This Is the Classic Flat Shoe Trend to Try Next
Could this be the new It flat shoe for fall?
-
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.
-
There's No Question—These 8 Fall Shoe Trends Will Make You Look Rich
Luxe outfits are in your future.
-
I Live in Murray Hill—Here Are the 8 Places I Like to Shop for a Fashionable Fall Closet
Stylish sweaters and suedes ahead.