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
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.
Say hello to the shoe trend that's both cool and practical.
These also come in black, but I like how the white pair shows off the shoe's texture.
In case anyone cares, I just ordered this pair.
Oh, Tibi. You always get it.
Vagabond makes some of the most comfortable, long-lasting shoes around, IMO.
Heeled Loafers
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.
NYC girls are flipping out over this emerging shoe brand.
This is the dreamy pair you've seen making the rounds on Instagram.
Pair these with mesh socks for a very of-the-moment retro feel.
In snakeskin print, loafers go from boring to must-have.
Who What Wear readers are shopping this pair en masse.
Combat Boots
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 always manages to make its staple items into something beautiful.
Classics for a reason (because you'll never tire of them).
White combat boots feel especially fresh.
Zara fans, where ya at?
These feel a tad more trend-driven thanks to the subtle platform.
Ballet Flats
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.
A fashion-girl and fashion-editor fave.
I'm sorry, but is this not the best $15 you'll spend all month?
Meet my dream shoes.
You probably need these in all four colors.
About as timeless as it gets.
Knee-High Boots
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.
A pair you'll own for years and years.
Snakeskin is everywhere this season.
You own a zillion black boots already, so why not consider an equally versatile burgundy pair?
If I didn't know these were H&M, I would assume they were designer.
I can't quite put my finger on it but something about these feels undeniably French.
Speaking of shoes, feast your eyes on the prettiest pairs of the season.
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Amal Clooney's Croc-Embossed Thigh-High Boots Are About to Cause a StirGuaranteed.
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These 5 Inspiring Outfits Are Proof You Can Easily Merge Classic and Trendy StylesTrust me, you're going to want to re-create these looks.
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The $25 H&M and $50 Zara Flats I'm Buying Because This Shoe Trend Is Suddenly EverywhereIt's good enough to buy in multiples.
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The 2025 It Girl's Wardrobe: 9 Highly Specific Brands and Buys They're All WearingFrom handbags to jeans to jewelry.
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The Boot Trend Everyone With Expensive Taste Is Styling Instead of Flats or HeelsWe're here for it.
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Not Sneakers and Not Ballerinas—This Flat-Shoe Trend Is Far Chicer for SpringAny guesses?
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The Unexpected Shoe Trend Bella Hadid's Been Wearing Right and Left During Paris Fashion WeekForget flats—buy these instead.
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The Pretty Flats Trend Katie Holmes Just Wore Makes Jeans Look High-EndFound my next purchase.
