Winter boots 2019

Global warming’s got the weather a little skitso. But it’s still winter, and as good as the weather feels today, it’ll probably be ugly tomorrow. When the weather turns, make sure you’re prepared with a good pair of boots.

Timberland GT Rally Mixed-Media Boot

Comfort is a major selling point for this retro-styled hiker. Features a leather and mesh upper, OrthoLite® footbeds, and Timberland’s SensorFlex™ technology for ultimate cushioning and shock absorption.

Timberland GT Rally Mixed-Media Boot

SOREL Madson Chukka Boots

SOREL calls their Madson chukka timeless, they’re not wrong. This boot will pull together almost any look, dressy or casual. Best of all, they’re waterproof, making them functional in the winter months.

$170
MADSON™ CHUKKA BOOT

Boulder Chukka by Lems

Unlike other chukkas, the Boulder Chukka by Lems packs air-injected rubber outsole under it’s suede upper, leaving it lightweight, and flexible, while maintaining lots of traction.

$120
Lems Boulder chukka boot

Quoddy Bowhunter Boot

There are better alternatives if you’re going to slog through snow banks and rain storms, but the handsome classic styling of the Quoddy Bowhunter boot is a great addition to a casual dress code.

$310
Quoddy Bowhunter boot

Squall Canyon D-Ring Chukka Boots

With premium materials including full-grain leather, OrthoLite® footbeds, Rubber outsoles, MirrorFit™ comfort system, and TimberDry™ waterproofing the Squall Canyon D-Ring Chukka is one of Timberland’s best boots.

$165
Squall Canyon Waterproof D-Ring Chukka Boots

Andreas Hiking boot by ROA

This Italian import’s 100% rubber sole will keep you sure footed. The outer portion is a combination of leather, and polyamide, with the collar and tongue wrapped in insulating metallic foil.

$414
ROA Andreas hiking boot

POLO Army Boot

It’s hard to argue against the timelessness of Ralph Lauren. The POLO Army boot is no exception. Like it’s cousin, the Ranger boot (or Cookie boot to Lo heads), the durable Army is a call back to early ’90s Ralph Lauren.

$165
Ralph Lauren POLO Army Boot

UGG® Zetik Waterproof Rain Boot

You know what’s worse than going to work on a rainy Monday morning? Going to work on a rainy Monday morning in wet socks. These duck boots keep the rain out, while adding style to your

$115
UGG® Zetik Waterproof Rain Boot

Columbia Newton Ridge Plus II

Leather, suede, and mesh upper combined with a lightweight, non-slip rubber outsole to make the Newton Ridge Plus II perfect for trekking through snowy, rainy sidewalks.

Columbia Newton Ridge Plus II

6-Inch Construction Tims

Every self-respecting New Yorker’s got a pair of construction Tims in their closet, B. The yellow 6-inch boot is a classic, and has been a mainstay of the urban wardrobe since 1989.

$198
6 inch Construction Tims

Colonial Plain Toe Boot

The Colonial Plain Toe boot is going to set up back a few pennies, but hear me out. Every guy needs a stylish go-to casual shoe. The Colonial fits the bill, and is super comfortable. There are cheaper alternatives, but if you can afford it, cop these.

$565
Colonial Plain Toe Boot
Daniel Cruz

With an interest in pop culture, Daniel Cruz's writing centers around the things he loves best: Music, Film, and Art.

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