Men’s Winter Boots From Cole Haan, Tecovas, and More Are on Sale up to 65% Off

3 min read

• As we head into Presidents’ Day weekend, brands are starting to mark down some of their best winter boots and gear.
• Take up to 65% off editor-approved styles from Cole Haan, L.L. Bean, Johnston & Murphy, and more.
• We’ve hand-tested the majority of the boots on this list, and they’re now cheaper than ever.

IN THE BRUTAL cold, the first thing to freeze is your extremities. And while hopefully your situation isn’t that dire, cold feet are not fun. You’re going to need those dogs in tip top shape to work off this year’s hibernation weight (perfect for retaining muscle, if nothing else), so it’s imperative to keep them as healthy as possible. That’s why we’re always testing and recommending the best boots for loyal readers.

Luckily, a bunch of our favorites are on sale, as we approach the home stretch of one of the worst winters here on the East Coast in recent memory. The glass-half-full approach here is knowing you can still get plenty of use out of your brand-new boots for a fraction of the price. From style-forward dress boots to rugged outdoor options, we scoured the web and found savings up to 65 percent off. If you waited all year for a discount on winter weather gear (and probably regret it), it’s not too late to enjoy some worthy deals.

Best Sales on Winter Boots

Warmest Winter Boot

L.L.Bean Shearling Lined Bean Boots

Now 33% Off

Best for Everyday Wear

Cole Haan Originalgrand Remastered Waterproof Chukka Boots

Now 30% Off

Best Hybrid Boot

Cole Haan ØriginalGrand CitySpectre Chelsea Boots

Now 57% Off

Best for Hiking

Merrell Coldpack 3 Thermo Mid Waterproof

Now 25% Off

Top Budget Pick

NORTIV 8 Ankle High Waterproof Hiking Boots

Rugged Style

Dr. Martens Waxy Commander 1460

Now 30% Off

Best Cowboy Winter Boot

Tecovas The Rugged Roper

Now 41% Off

Best All-Season

Clarks Bushacre 2 Chukka Boot

Now 48% Off

Comfiest Chelsea Boot

Amberjack The Chelsea

Now 15% Off

Best Stylish Work Boot

Danner Douglas GTX

Now 65% Off

Best Leather

Beckett Simonon Bolton Chelsea Boots

Now 36% Off

Best for Outdoor Work

Timberland PRO MaxTRAX Slip-Resistant Work Boot

Now 23% Off

Our editors are huge fans of Cole Haan’s ultra-comfortable hybrid dress shoes, both in and out of the office. There are a couple of notable styles on sale: the versatile, all-season ØriginalGrand Remastered Waterproof Chukka Boots are 30 percent off on Zappos (the lowest price we’ve seen all winter), and the editor-tested ØriginalGrand CitySpectre Chelsea Boots are 57 percent off on Cole Haan’s site. You can’t go wrong with either one.

I’ve been wearing my Bean Boots almost every day since the weather took a turn for the worse, and they’re probably the best blend of comfort, insulation, and durability. I usually rock the unlined version, but if you want to take it up a notch, the Shearling Lined Bean Boots are currently 33 percent off on the L.L. Bean site. You’re going to want to act fast, though, because they’re already sold out in quite a few sizes and styles. L.L. Bean’s greatest winter sale is also happening now, so there might be some other options that catch your eye.

Huckberry has some residual savings from its own winter sale. For example, the ultra-rugged Dr. Martens Waxy Commander 1460 is still 30 percent off. This pair is a little more heavy-duty, but perfect for cold weather and built to last for years.

I’ve only recently become a Chelsea boot fan, and Amberjack makes some of the most comfortable ones on the market. They’re 15 percent off on Amberjack’s site, bringing the price under $200. I love my Danner Boots when I want to find the perfect balance of style and functionality. Now’s as good a time as any to buy, as the Douglas GTX is a whopping 65 percent off for a limited time.

Other standout deals include almost 40 percent off the similarly editor-tested Beckett Simonon Bolton Chelsea Boots, 25 percent off a pair of our favorite hiking boots, the NORTIV 8 Ankle High Waterproof Hiking Boots, and 45 percent off the stylish Clarks Bushacre 2 Chukka Boot.

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Tim Kohut is the Deals and Trends Editor for Popular Mechanics, Men’s Health, Best Products, and Runner’s World. He has extensive product review and gear coverage expertise, particularly in tech, home, auto, and health. Tim was previously the Deputy Commerce Editor of The Drive and a Commerce Editor at BGR. He’s also overseen gear coverage and strategy at Popular Science, Bob Vila, Outdoor Life, and Field and Stream. He has a strong affinity for cats, Batman, and early 90’s Nicolas Cage films, in that order.

As the Style and Commerce Editor for Men’s Health, Joseph covers all-things fashion and grooming. Previously, Cheatham was a commerce editor for Spy, and he has written for Travel + Leisure.