How to Pick the Right Boots, According to Menswear Experts

I WALK A LOT. Not just from my New York City apartment to the subway and then the office, but across town for meetings, errands that pile up on the same day, and the occasional detour to grab a coffee or check out a new shop. By the time winter hits, my boots get tested in every condition the city can throw at me: icy sidewalks, slushy streets, and salt that eats leather faster than you’d expect.

I’ve also made the rookie mistake: buying boots that looked great but were stiff as a board, convincing myself they’d magically soften up after a week of wear. Spoiler: they didn’t. I’ve learned that some boots demand a serious break-in period, and some never really get comfortable at all. After years of testing boots the only way that really counts—by walking miles in them—I’ve landed on a few non-negotiables I look for every winter. Fit, materials, soles, and where I’m actually wearing them all matter. Get those right, and you end up with boots you rely on all season.

Your winter boots should match your lifestyle, not just your outfit. No single pair does everything well, so I think about boots in terms of where I’m going and how much walking the day actually involves.

For Work and Office Days

If I’m heading into the office or have meetings that skew more polished, I reach for dress boots, cowboy boots, or cap-toe styles. You want something that can move across different kinds of dress codes, whether you’re in a casual environment where jeans are the norm, a more traditional setting that calls for a blazer, or one that involves being on your feet all day. A rubber sole—or at least a discreet lug—goes a long way here. In all of those cases, the goal is the same: a boot that complements what you’re wearing without feeling out of place.

Bolton Chelsea Boots

Beckett Simonon Bolton Chelsea Boots

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Campus Inside Zip

Smooth Leather Moc Toe Boot

Banana Republic Smooth Leather Moc Toe Boot

Now 50% Off

For Commuting and Bad Weather

When the forecast is ugly or I know I’ll be outside a lot, rugged waterproof boots are non-negotiable. I stick to black, dark brown, or deep charcoal. These colors hide salt stains and scuffs better and still pair easily with most winter wardrobes. A round or slightly almond-shaped toe works best. I wear them with jeans, heavier chinos, and workwear-style pants, especially when layering up top. These boots prioritize traction, insulation, and durability, which matters when you’re navigating slush, puddles, and uneven sidewalks. This is where brands like Blundstone, Danner, and Red Wing shine.

Classic Moc

Red Wing Shoes Classic Moc

#585 Chelsea Boot

Blundstone #585 Chelsea Boot

Mountain Light

For Everyday, In-Between Days

Most winter days fall somewhere in the middle, which is where lace-up casual boots and moc-toe styles come in. For everyday wear, I like medium to dark brown, rich cognac, or even a muted burgundy. These colors add warmth and depth to an outfit without being loud. Think Red Wing moc toes or a Timberland-style silhouette. They sit comfortably between rugged and refined—sturdy enough for long walks and commutes, but not so bulky that they feel overbuilt. These are my go-to boots for errands, casual meetings, and days that start early and end late.

8847 Classic Moc Leather Boots

Red Wing 8847 Classic Moc Leather Boots

Roundhill Grand Waterproof Chelsea Boots

Cole Haan Roundhill Grand Waterproof Chelsea Boots

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For Casual Plans and Light Wear

When I know I won’t be dealing with bad weather, I lean into boots that are more about style than protection. Suede or smooth leather in lighter brown, tan, or taupe works well here, especially when treated with a weatherproofing spray. I stick to a round or slightly tapered toe, which keeps the relaxed look and doesn’t look overly formal. They’re my go-to for dinners, casual hangs, or quick walks around the neighborhood.

Nomad Boot

Chandler Chukka Boot

Allen Edmonds Chandler Chukka Boot

Style-First Boots

Style-first boots—like cowboy or Western-inspired styles—are more about personality than practicality in winter. When I wear them, I stick to black, dark brown, or deep burgundy, which feel elevated and seasonal. A pointed or squared toe is part of the look here, and it’s what gives these boots their edge. They pair best with straight-leg or relaxed jeans and simple layers up top, letting the boots do the talking.

The Cartwright