Shoes
Dec 1, 2019

Every Pair of Boring Shoes You'll Need for Winter 2019

by Anna LaPlaca

best shoes for winter

Photo:

SZYMON BRZÓSKA/THE STYLE STALKER

Some of the best things in fashion are deemed "boring." Think about it: The blazers that work the hardest in our wardrobes, the plain tees we wear on repeat, and the neutrals that go with literally everything. We could go on, but we think you get the gist. Boring obviously isn't a bad thing in this context. Actually, it's quite the opposite. The classic staple pieces that you've owned and worn for years? Maybe they're not the most trendy or buzzy, but they're definitely the most valuable.

It's through that lens that we're looking at our shoe collections right now. More than any other season, winter is the time to think with practicality in mind first when getting dressed. But, us being the fashion people, we're hardly letting style take a backseat to function. Enter the boring but amazing shoes we're adding to our arsenals ahead of winter. From the lug-sole boots that are equally functional and fashionable to the flats you need to reconsider wearing again, scroll down to discover why we're naming the following five styles the best shoes for winter and shop the pairs we love within each category.

lug-sole boots for winter

Photo:

@discodaydream

Wear lug-sole boots now to nail the chunky-sole shoe trend and then once winter weather really hits, put them on to combat rain and snow. It's truly a shoe trend that does both.

ATP Atelier Catania Boots

Say hello to the shoe trend that's both cool and practical.

Rag & Bone Shawn Chelsea Booties

Shawn Chelsea Booties

These also come in black, but I like how the white pair shows off the shoe's texture.

Dr. Martens 2976 Quad Chelsea Boots

2976 Quad Chelsea Boots

In case anyone cares, I just ordered this pair.

Tibi Diego Boots

Oh, Tibi. You always get it.

Vagabond Shoemakers Kenova Lugged Chelsea Boot

Vagabond Shoemakers

Kenova Lugged Chelsea Boot

Vagabond makes some of the most comfortable, long-lasting shoes around, IMO.

heeled loafers for winter

Photo:

@double3xposure

Grandma dressing is on the rise and among the items defining the trend—oversize sunglasses, cardigans, layered sweaters—heeled loafers are emerging as the boring yet retro-cool shoe trend to try now.

Labucq Kitty Loafers

NYC girls are flipping out over this emerging shoe brand.

Gucci Leather Platform Loafers with Horsebit

Leather Platform Loafers with Horsebit

This is the dreamy pair you've seen making the rounds on Instagram.

Urban Outfitters Gema Chain Trim Heeled Loafer

Urban Outfitters

Gema Chain Trim Heeled Loafer

Pair these with mesh socks for a very of-the-moment retro feel.

Freda Salvador The Rock Mid Heel Loafers

The Rock Mid Heel Loafers

In snakeskin print, loafers go from boring to must-have.

Michael Michael Kors Buchanan Block Heel Loafer

Michael Michael Kors

Buchanan Block Heel Loafer

Who What Wear readers are shopping this pair en masse.

combat boots for winter

Photo:

@jen_wonders

If you recall, not too long ago combat boots were actually more of a trendy shoe pick, but recently they've become a staple in wardrobes everywhere. For winter especially, they're a practical pick to wear with your jeans and dresses.

The Row Fara Leather Ankle Boots

Fara Leather Ankle Boots

The Row always manages to make its staple items into something beautiful.

Vince Camuto Bestenda Combat Boot

Bestenda Combat Boot

Classics for a reason (because you'll never tire of them).

Thursday Boots Combat Boots

White combat boots feel especially fresh.

Steve Madden Tornado Combat Boot

Tornado Combat Boot

These feel a tad more trend-driven thanks to the subtle platform.

ballet flats for winter

Photo:

Ballet flats are having somewhat a renaissance. Have you noticed? Suddenly, designers are putting inventive new spins on the basic flats, and quite frankly we're here for it.

Urban Outfitters Tie Ballet Flat

Urban Outfitters

Tie Ballet Flat

I'm sorry, but is this not the best $15 you'll spend all month?

Mango Leather Flat Shoes

Leather Flat Shoes

You probably need these in all four colors.

Sam Edelman Felicia Flats

About as timeless as it gets.

knee-high boots for winter

Photo:

SZYMON BRZÓSKA/THE STYLE STALKER

I hardly need to explain how and why knee-high boots are trending at the moment, but I will explain that the buzzy pair is actually such a timeless pick. Sleek and elevated, they're the kind of boots you'll reach for over and over to add a luxurious element to any cold-weather look.

Sam Edelman Hiltin Knee High Boot

Hiltin Knee High Boot

A pair you'll own for years and years.

Schutz Maryana Pointy Toe Boot

Maryana Pointy Toe Boot

Snakeskin is everywhere this season.

Mango Leather High-Leg Boots

Leather High-Leg Boots

You own a zillion black boots already, so why not consider an equally versatile burgundy pair?

H&M Knee-High Boots

Knee-High Boots

If I didn't know these were H&M, I would assume they were designer.

Urban Outfitters Elle Knee-High Boot

Urban Outfitters

Elle Knee-High Boot

I can't quite put my finger on it but something about these feels undeniably French.