10 Chic City Winter Boots to Wear Now

Collection Style Life

When choosing boots that can withstand winter’s raging storms, it’s easy to get sucked into the classic debate of form versus function. Does one pick a sexy, chic boot and stay indoors when the winds howl? Or attempt to maneuver a sidewalk wearing something fashionable and fall flat on one’s ass. We’re about to end this conundrum for you! It’s actually possible to be fashionable and stay dry at the same time. Yaaass! Flirty footwear can be cozy and waterproof too. After checking out the shoes below, you’ll see the only decision you’ll have to make is which pair to bring home.

Read on for our favorite picks for the year’s cruelest and coldest months.


Bearpaw Joy, $89.99, Bearpaw 
Whether you’re tromping in the snow, navigating a slushy street or dealing with basic cold weather, Bearpaw’s Joy boots are incredibly warm. They feature a sheepskin-covered comfort footbed and convert quickly into a bootie, giving you two pairs of boots for the price of one. Go ahead and show off the knitted shaft. The suede exterior has been treated with Never Wet® by Rust-Oleum®, so rain and snow bounce off, never leaving a trace behind. More importantly, your feet never freeze. And yes, the sole has a rubber slim tread, which helps prevent sliding around the pavement. 


Aquatalia Viviana, $595, Aquatalia  The Duchess of Cambridge, Kate Middleton, is a big fan of this brand of Italian footwear — probably because all the boots they make are waterproof. Heel lovers won’t have to compromise style wearing the Viviana. Quilted suede uppers are lined with faux fur and the crepe wedge sole prevents slippage when it’s slick outside. They’ll keep you dry and warm even during the nastiest winter squall. 


Sporto Dena faux fur lined tall duck boot, $138.95, Nordstrom 
Do these boots bring back memories of college life or what? Duck boots were the only way you could walk across campus safely. They look just as awesome today paired with a denim mini, tights and a graphic print sweatshirt as they did when you were an undergrad (unless you are an undergrad, in which case you need to get your hands on these immediately). It’s the fortieth anniversary of the duck boot this year! To celebrate, Sporto gets all fashionista on us with a hand-lasted suede and leather upper. Inside there’s a warm faux fur and Thinsulate lining, and of course, it’s got that classic Vibram sole. The Dena boots may make you wish it would snow so you could kick off a snowball fight.


Sugar Raffle3 rain boots, $34.99, Belk 
Winter isn’t just about snowstorms, it’s also about miserable rain and freezing sleet, too. When it’s slushy, rainy or gray outside, add a spot of color with printed rain boots that will repel anything. Lined with fabric with a removable padded insole (a quick rinse stops that dreaded musky-foot smell), these durable rain boots might tempt you to stomp in a puddle or two like you did when you were a kid.


Khombu Alex quilted waterproof wedge boots, $95, Bloomingdale’s 
What’s so amazing about Khombu boots? They’ve sponsored the US Olympic ski team for years and with brand ambassadors like Abby Ghent and Erik Arvidsson, Khombu has learned, firsthand, what goes into creating excellent après ski boots. They’ve taken that knowledge and created smart streetwear for non-athletes like us. Waterproof Alex, made in America, has a slip-resistant K-guard sole, faux fur lining, faux suede shaft, memory foam insole and Thermolite insulation. The boot works well on city streets and on the trail to a toasty warm ski lodge.

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Lucky Brand Baselrain rain bootie, $78.95, Nordstrom 
Details like zippers on both sides and a stacked heel make Lucky Brand’s bootie look like it should never see bad weather. They actually resemble a smart leather bootie instead of good utilitarian footwear. Lined with fabric and a cushioned inner sole that make them even easier to wear, you might want to put them on when the sun’s out too.


Baretraps Hanelle bootie, $59.99, Footwear Unlimited 
Who isn’t obsessed with moto boots? From the moment Jennifer Aniston was spotted wearing moto boots back in 2011, they’ve become a fashion must-have. Baretraps make Hanelle, their winter version of a moto boot using a proprietary Stay Dry System. Every leather boot from Baretraps is outfitted with water-resistant tech, so water literally beads off the boot. They are also heavily insulated and the special rubber sole was designed with traction in mind. Hanelle not only has faux fur trim, the sole and lining are made with fleece.


Jack Rogers Chloe Classic all-weather boot, $118, Jack Rogers 
Chloe comes in every color of the rainbow, so if you’re not a fan of this shade, head on over to the site to find one that you like. Chloe’s like a Range Rover: a classic utilitarian object made chic by simply being what it is. The tough all-weather bootie silhouette had a makeover with a metallic shaft and Jack Rogers’ signature rondelles on the eyelets. Waterproof (of course), Chloe’s rubber sole provides traction and adds stability when walking on slippery, snowy surfaces.


Cole Haan Hastings waterproof bootie, $89.99, Saks Fifth Avenue Off Fifth
With its soft suede upper and brass buckle detail at the shaft of the boot, you’d be tempted to dismiss this Cole Haan bootie as just a fashionable item that can’t handle stormy climes. Not so! Completely waterproof with a rubber sole and lined to prevent soggy toes, this boot can be worn whether it’s sunny or not.


Baretraps Zeldie bootie, $59.99, Footwear Unlimited 
The Zeldie comes in three colors: black, brown and gray. In gray, the shaft of this suede/microfiber boot boasts a Nordic print, turning the silhouette from city chic to boho babe. Either way, it’s easy to get obsessed with the bootie. While made with Baretrap’s proprietary Stay Dry System tech, the stacked and lugged sole are on-point with winter trends. Lined with fleece and featuring a hidden stretch panel, these boots not only protect you from the elements, they keep your feet dry and warm.


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