3 Warm Winter Boots Chicagoans Are Wearing This Season

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Preparing for a brutally frigid winter means knowing the right cold weather clothing staples to look for. And who better to advise on the pieces that’ll get you through the coldest months than someone from a city where staying warm in the winter is truly a feat. Yes, we’re talking about Chicago, where a typical winter brings an average of 37 inches of snow with temps hovering around 30 degrees Fahrenheit (not to mention the relentless, bone-chilling breeze brought to you by the gorgeous Lake Michigan). Whether you’re from the great state of Illinois or just looking to Chi-Town locals for cold weather fashion advice, here are three winter boot styles that will keep you dry and warm no matter the forecast.

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1 sorel leather

1. sorel Brex Boots

Best Waterproof Boots

If you’re in the market of a pair of sensible winter boots that you don’t need to change out of when you get to the office, we recommend a pair like these Sorel Brex Boots. Avoid the extra step of throwing another pair of shoes in your bag and just get a pair that can withstand the snowy conditions. You can usually find a solid pair of leather booties or knee-high boots that boast a waterproof upper, so your feet don’t get wet from melting snow and slushy crosswalks. One reviewer raves, “I LOVE THIS BOOT. Everything I've been looking for in a daily-wear boot: comfort, support, weather-safe and heavily industrial style.” Customers say they run a bit tight—and you’ll want to wear some thick socks to lock in the warmth—so consider sizing up for plenty of room.

north face chilkat
The North Face

2. the North Face Chilkat 400 Boots

Best Insulated Boots

This style of boot is crafted to sustain bitter cold winter weather conditions. The insulation will offer deluxe warmth and protection to your feet and legs from the chilly air. Insulated boots trap the feet-generated warmth inside the shoe and doesn’t allow the outside cold in making these the best option if you are outside for long periods of time. This pair from North Face has an EVA midsole for ultimate comfort while walking, a waterproof outer layer and are made of recycled contents. One New York-based customer writes, “Love these boots! Everyone keeps saying how cute they are. The best part is my feet are usually freezing every year. Now my toes are nice and toasty. It seemed like no matter what kind of boots I would wear they would never keep my feet warm and dry. These boots do both and look cute doing it. Buy these boots you won't be disappointed!”

madewell sneaker

3. madewell The Sneaker Boot

Best Boots for Walking

Whether you love taking your dog on long walks or just don’t like taking the crowded Red Line to River North, boots that sit lower on your shins are fabulous for walking a lot, since they allow more movement while still keeping your feet warm. If you’re grabbing a pair because you’re always out and about on foot, be sure they have cushioned insoles for comfort and performative traction on the soles to avoid sliding on slick surfaces like this pair from Madewell. This bestselling hybrid shoe combines the comfort and mobility of a sneaker and the warmth of a winter boot—what more could you ask for while you holiday shop?

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Olivia Dubyak

Commerce Editor

Olivia Dubyak is PureWow's Commerce Editor and textbook Capricorn. She studied journalism at Duquesne University in Pittsburgh, Pennsylvania, but has gone from New York City to...
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