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

by Anna LaPlaca

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.

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 ($513)

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

Rag & Bone Shawn Chelsea Booties ($550)

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

Dr. Martens 2976 Quad Chelsea Boots ($180)

In case anyone cares, I just ordered this pair.

Tibi Diego Boots ($595)

Oh, Tibi. You always get it.

Vagabond Shoemakers Kenova Lugged Chelsea Boot ($140)

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

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 ($350)

NYC girls are flipping out over this emerging shoe brand.

Gucci Leather Platform Loafers with Horsebit ($980)

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

Urban Outfitters Gema Chain Trim Heeled Loafer ~~( $69)~~ $49

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

Freda Salvador The Rock Mid Heel Loafers ($450)

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

Michael Michael Kors Buchanan Block Heel Loafer ($99)

Who What Wear readers are shopping this pair en masse.

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 ($1390)

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

Vince Camuto Bestenda Combat Boot ($149)

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

Thursday Boots Combat Boots ($180)

White combat boots feel especially fresh.

Steve Madden Tornado Combat Boot ($110)

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

Photo:

@ANJASCNK

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 ~~( $29)~~ $15

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

Mango Leather Flat Shoes ($80)

You probably need these in all four colors.

Sam Edelman Felicia Flats ($100)

About as timeless as it gets.

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.