An Authoritative Guide to Choosing the Right Pair of Winter Boots

Sharp Staff December 6, 2018

Boots are like cats — there are many ways to skin them. And by skin, we mean wear. This wonky analogy aside, what we’re trying to say is there is no singular, perfect winter boot. Different occasions (and climates) call for different styles. From a short, laidback chukka for the office to an elegant, pull-up dress boot for a night on the town, there’s a great variety of pairs for a great variety of tastes and needs. We took it upon ourselves to break it all down for you, using the robust boot collection from Kenneth Cole Reaction.

Jace Lace-Up Boot

A synthetic upper with a perforated design and contrasting panel gives this pair the rugged aesthetic of a combat boot. Ideal for a concert and/or motorcycle ride. (Okay, even if you don’t ride motorcycles, you can at least look like you do.)

$122, THEBAY.COM

Daxten Leather Boot

These on-trend boots, crafted from leather, are tough and versatile enough to rock on the 9-to-5 and wicked weekend alike.

$136, THEBAY.COM

Klay Lace-Up Boot

With their leather and wool uppers, and wing-tip and broguing detail, these boots were made for walking…into the boardroom.

$122, THEBAY.COM

Uptown Chukka Boot

Who doesn’t like a good chukka? This classic nubuck pair is dressy without being too dressy. Good for the weekday and the weekend. Virtually indestructible, too. Finally, a desert boot you can wear all winter.

$95, THEBAY.COM

Casino Chukka Boot

Another iteration of the desert boot. And, like the OG chukkas worn by British soldiers during World War II, this tough-as-nails pair straddles the line between formal and fight-ready.