Every product was carefully curated by an Esquire editor. We may earn a commission from these links.
Rain and snow have nothing on these styles. Winter Fashion Casual Boots
Boots are an obvious winter footwear choice. They're warm, they're sturdy, they're protective. But they're not all waterproof.
If you're going to step outside even once this winter—and I'm willing to bet a lot of money that you are—you need a staple waterproof boot on your side. When it snows or rains, they're the only thing standing between you and a damp, cold, squelching sock. In the aftermath of snow and rain, too, they're your first line of defense against puddles and mud.
Whether you're a city guy or you're out in the suburbs or great outdoors, there's a waterproof boot for you, and trust me, no matter where you are, you're going to need one. If you want to keep things sleek and classy, you can snag a brogue boot from Allen Edmonds, or opt for a classic Chelsea boot from brands like Ugg and Chaco. If you're braving the winter weather outdoors, get a functional, protective style equipped to take you anywhere—On, Carhartt, Arc'teryx, Columbia, and Timberland have great picks. And if you just want to keep things simple and suave, well, there are styles from Canada Goose, Clarks, and Hunter that are certifiable staples. Whatever suits your fancy is right here—and it'll keep you toasty and dry.
Simple, cool, and casual. When you see a puddle, feel free to jump in it, as long as you have these on.
A timeless moc toe style, with traction and a waterproof fabric that doesn't sacrifice style for functionality.
For a heavy-duty option, Columbia's waterproof boots will keep your feet more dry than if you held them under a hand dryer.
With a thick rubber sole, tons of traction, secure lacing, and a leather exterior, these boots really do have it all.
In case the waterproof upper wasn't enough for you, the toe of these boots is extra-equipped for wet weather, with a hard shell encasing the lower half.
Not all waterproof boots have the be chunky and heavy, though. Allen Edmonds proves it, with these chukka boots that have a gorgeous brogue detail.
Uggs are certifiable winter boot specialists, and their all-black, sleek Chelsea boots depart from the classic cozy and fuzzy look.
The quintessential "I'm going to go splash in that puddle" boot. Tried and true, baby.
The Chelsea boot is a timelessly classy style, and thank goodness for brands like Chaco, who are here to offer waterproof renditions.
These might not look waterproof, which heightens their versatile appeal. Wear 'em when it's dry, wear 'em when it's wet—your feet will feel the same either way.
Your favorite sneaker maker has a gore-tex hiking boot that'll keep your feet nice and dry during a winter stroll.
A cool hybrid between a high-top sneaker and a mesh hiking shoe, these waterproof boots from On add two things to your outfit: style and safety (from water, that is).
A go-to, no-nonsense Chelsea boot that's—you guessed it—100 percent waterproof.
For an option that basically contours to your foot, try Arc'teryx's sock-like waterproof boot; it's lightweight, comfy AF, and looks damn cool.
If you want some extra warmth and protection, Carhartt has a knee-high, waterproof boot with a thick sole that's durable and cushiony.
If anyone knows winter, it's TNF. Their mid-top waterproof boots have the casual appeal of a sneaker.
For something that truly says "I'm ready for winter," Canada Goose's puffer boots are a solid choice (that pair very well with a puffer jacket, BTW).
Trishna Rikhy is the Associate Style Commerce Editor at Esquire. Previously, her writing has appeared in Vogue Runway, PAPER Magazine, V Magazine, V MAN, and more. She is based in NYC, but can probably be found wherever the strongest cup of coffee is.
The Best Items from New Balance's November Sale
There Really Is a Flannel Shirt For Everyone
Banana Republic's Suede Jacket Is a Scene-Stealer
The 22 Best Cashmere Sweaters For Men
The Best J.Crew Sale Items to Shop Right Now
What's Next for C.P. Company?
The 20 Best Boxer Shorts to Wear Every Day
The 23 Best Rain Boots to Keep Your Feet Dry
Jalen Brunson on Tunnel Fits and NBA Fashion
The 14 Best Ski Jackets For a Day on the Slopes
This Week's Best Menswear Releases
Thermal Shirts are the Solution to Weird Weather
A Part of Hearst Digital Media
We may earn commission from links on this page, but we only recommend products we back.
Winter Lace-Up Work Boots ©2023 Hearst Magazine Media, Inc. All Rights Reserved.