10 Best Boots for Men for Every Occassion This Winter: Chukka, Chelsea, Hiking and More

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cole haan boots
Cole Haan

Whether you prioritize fashion or function, save on durable, stylish Cole Haan boots to wear all season long.

Now that the winter chill is starting to set in, weather-proof attire is a necessity. Before the temperatures really start to drop and snow hits the streets, it's time to stock up on cold-weather essentials: warm jackets, hats, gloves, and, of course, a really good pair of boots.

Whether you purchase them for fashion or function, a proper pair of winter boots should feature waterproofed outers, slip-resistant soles, and plenty of arch support. Cole Haan, an American authority in footwear and accessories, has a wide selection of boots for men — and right now, they're on sale for up to 60% off. You can save on elegant chukka boots, durable hiking boots, versatile Chelsea boots, and so much more for braving the incoming weather in style.

Shop Cole Haan Men's Boots

Whether you're the outdoorsy type looking for some weatherproof hiking shoes, want to make a fashion statement despite the cold or need a warmer pair of office shoes, Cole Haan has your winter boot needs covered — at a discount for a limited time. Below, check out ten of our favorite Cole Haan boots to shop this season.

American Classics Kiltie Chukka Boot

American Classics Kiltie Chukka Boot
Cole Haan

American Classics Kiltie Chukka Boot

These gorgeous chukka boots feature hand-sewn moccasin construction, arch cushions, and a lightweight EVA footbed.

$180 $80

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ZERØGRAND Chukka Boot

ZERØGRAND Chukka Boot
Cole Haan

ZERØGRAND Chukka Boot

Elevated elements such as chunky lug soles and welt detailing take these simple boots up a notch.

$238 $90

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The Go-To Lace Chukka Boot

The Go-To Lace Chukka Boot
Cole Haan

The Go-To Lace Chukka Boot

Sleek and elegant, these boots can easily be worn to work, fancy dinners and walking around town.

$250 $80

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5.ZERØGRAND Explore Chelsea Boot

5.ZERØGRAND Explore Chelsea Boot
Cole Haan

5.ZERØGRAND Explore Chelsea Boot

Non-slip rubber soles, waterproof materials, and thermal insulation allow these boots to withstand the winter weather.

$220 $80

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ZERØGRAND Hiker Boot

ZERØGRAND Hiker Boot
Cole Haan

ZERØGRAND Hiker Boot

Take 60% off these buttery cognac brown leather boots, complete with a cushioned footbed and collar detail.

$330 $100

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Wagner Grand Apron Chukka Boot

Wagner Grand Apron Chukka Boot
Cole Haan

Wagner Grand Apron Chukka Boot

Another understated black pick, these chukka boots are crafted with waterproof leather and rubber outsole to withstand winter weather.

$300 $130

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5.ZERØGRAND Explore Hiker Boot

5.ZERØGRAND Explore Hiker Boot
Cole Haan

5.ZERØGRAND Explore Hiker Boot

Don't let snow and ice stop you from enjoying the great outdoors. These hiking boots are fully equipped with a durable non-slip sole, thermal insulation and a flexible, cushioned midsole.

$220 $120

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Wagner Grand Chelsea Boot

Wagner Grand Chelsea Boot
Cole Haan

Wagner Grand Chelsea Boot

"These are my favorite pair of boots!" wrote one happy reviewer about these elegant Chelsea boots. "I can wear them with a variety of outfits and they are comfortable. These boots are the best footwear purchase that I have made in recent times."

$300 $150

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4.ZERØGRAND City Trekker Boot

4.ZERØGRAND City Trekker Boot
Cole Haan

4.ZERØGRAND City Trekker Boot

Make a statement in Cole Haan's City Trekker boot, available in black, olive, and this oatmeal beige.

$238 $120

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American Classics Plain Toe Boot

American Classics Plain Toe Boot
Cole Haan

American Classics Plain Toe Boot

Complete with a rugged tread pattern, leather arch support and lace-up closure, these boots are a balance of fashion and function.

$200 $140

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