The Best Winter Walking Shoes That Won’t Ruin Your Outfit

Photo by Lucretius Mooka

When winter hits, most of us trade style for survival—because slush and cute shoes rarely coexist. But that doesn’t mean you have to give up on looking put-together. The truth is, comfortable shoes have evolved. You no longer have to choose between waterproof soles and aesthetic appeal.

As someone who walks almost everywhere (and refuses to wear ugly shoes while doing it), I’ve spent enough winters testing what actually holds up—literally. The best walking shoes for winter share three things in common: traction, structure, and style. They can handle icy sidewalks, keep your feet warm, and still look good with your favorite wool coat or wide-leg trousers.

Here’s what’s trending this season—and what makes each one worth wearing.

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1. The Polished Elevated Sneakers

The elevated sneaker is winter’s MVP. Look for sleek leather finishes, minimal branding, and a slightly thicker sole for cold-weather durability. They go with everything from jeans to midi skirts and can survive slush with a quick wipe-down.

Style it with: cropped trousers, an oversized scarf, and a long wool coat for that off-duty editor energy.

Cloudnova 2 Sneakers

$170

Handball Spezial Sneaker

adidas

$110.00

GEL-1130™ Sneaker

$100

2. The Weather-Resistant Chelsea Boot

Think of these as the grown-up version of your rain boots—sleek enough for work, sturdy enough for ice. The elastic side panels make them easy to slip on and off, while lug soles keep you upright when sidewalks turn into obstacle courses.

Style it with: straight-leg jeans and an oversized sweater for casual days, or a knit dress for city walks.

Steve Madden

Blitzen Platform Chelsea Boot

$149.95

Slip On Ankle Booties

$45.99

Tall Riding Boots

$54.99

3. The Shearling-Lined Shoes

Part cozy slipper, part street shoe. These are perfect for days when it’s cold but not snowing yet. The fleece lining adds insulation, and neutral tones make them surprisingly versatile.

Style it with: leggings, long socks, and a quilted jacket for coffee runs or travel days.

Notice Faux Shearling Sneaker

Dolce Vita

$125.00

Skyla Faux Fur Lined Mule

VANELi

$184.95

Fern 2 Genuine Shearling Clog

Veronica Beard

$375

4. The Lug-Sole Loafer

Yes, you can wear loafers in winter. A chunky lug sole gives them grip, while the structured design keeps your outfit feeling smart. Perfect for days when you want to feel dressed-up without resorting to heels.

Style it with: trousers, turtlenecks, and a longline blazer. Add a trench or puffer depending on the temperature.

The Lug Loafer

Rothy's

$229.00

5. The Hybrid Boot-Sneaker

If you live somewhere that can’t decide between rain and snow, these are your best friend. Waterproof, shock-absorbent, and surprisingly light, they bridge the gap between hiking boot and fashion sneaker.

Style it with: joggers or denim, a cozy knit, and a cropped puffer.

Amazon

Kinetic Impact Caribou Waterproof Shoes

$164.00

6. The Sleek Puffer Boot

This trend hit quietly, but it’s here to stay. Puffer boots are lightweight, warm, and perfect for travel days when you want to keep your airport look stylish but practical.

Style it with: leggings, a long padded coat, and a scarf you can wrap twice for drama.

Amazon

Waterproof Ankle Booties,

$56.99

7. The Elevated Winter Boot

There’s a new wave of winter boots that are practical without looking bulky—sleek silhouettes, faux-fur lining, and a subtle heel for lift. They make trudging through snow feel less like a chore and more like a runway walk.

Style it with: jeans tucked in, an oversized coat, and a beanie that feels intentional, not accidental.

Suede Faux Fur Lining Anti-Slip Warm Winter Booties

$49.99

Ultra Mini Classic Boot

UGG®

$159

Bailey Bow II Genuine Shearling Boot

UGG

$209.95