This site has limited support for your browser. We recommend switching to Edge, Chrome, Safari, or Firefox.

Complimentary FREE SHIPPING on most Canadian orders over $150* full details (416) 367-4335

Men's Winter Looks Feature

winter boots men

As we enter another snowy week, it’s hard to get motivated to leave the house – or even our beds for that matter. The same old snow gear gets old, and it’s always helpful to get a fashionable nudge to see that style is still possible even in the slush! We’ve put together a few winter looks for our men, that will highlight some of our best boots that can complement almost any look. Read on!

The One That Walks to Work

Looking for a stylish, yet waterproof pair of soles that you don’t have to take on and off after your commute? Look to anything like the Cougar Crowley-L Winter Boot, a 7 inch-tall rugged leather chelsea boot, complete with a rubber outsoled anti-slip mud guard, waterproof exterior, and a -30C temperature rated fleece lining. Perfect to pair with your business-casual get up and walk you right into work.

The Errand Buddy

Taking the kids to hockey practice? Grabbing groceries? We understand – no one wants to run errands in a bulky pair of snow boots. Slip on a pair of Cole Haan Wagner Chelsea Boots. Flawlessly crafted in sleek waterproof leather, the Wagner Grand Chelsea will make a suave addition to your boot arsenal. This boot is chock full of proprietary elements that include Grand.OS chassis shank and Grand.OS energy foam for comfort. No one likes opening up their car door to a deep puddle, pull on Swim’s Galoshes to add some extra protection to your favourite pair of shoes. Rain, snow, or sleet is simply no match for this pair.

The Slope-mate

Headed to the mountain this weekend? Invest in a pair of heavy-duty boots like the Cougar Serge 2 Winter Boot to walk you through that powder effortlessly. With a molded base, this mid-calf boot complete with front lacing and a bellows tongue promises to keep you warm and dry through harsh climates. The always waterproof shoe is temperature rated for as low as -30C with its polar plush lining and memory molded Insole. Its rugged outsole tread is guaranteed anti-slip.

The One You Can Dress Up

Looking for a dress shoe that provides you with all day comfort? Look to Cole Haan’s Washington Whole Cut shoe, perfect to take you from the office, to out on the town. This dress shoe unites traditional craft with modern engineering. Each innovation works harmoniously with the next uniting lightweight and cushioned energy foam a precision-engineered footbed and full-motion outsole for flexibility and comfort. It’s debossed leather outsole supplies its wearer with a unique look, as no two shoes are the same. The running shoe-inspired energy foam responsively cushions and aids each step while its torsional arch supports and steadies every movement.

The One to Tide You Over

As the weather is flip flopping, it’s good to have a shoe for the in-between season, something for milder days that may not be as light as a loafer, but not heavy enough to be a boot. Turn to Swims’ Breeze Knit Tennis shoe, a look that reimagines the classic tennis shoe for the man on the go. Lightweight, flexible, and breathable, it features a rubber cup-sole for durability and traction plus an EVA midsole for extra cushioning. A versatile standby for active days that allows for ventilation and promotes dryness, employing a breathable fabric designed specifically to transmit sweat and moisture from the inside to the outside.  The outer-sole’s specially designed and fabricated treads provide better grip and safer mobility, allowing wearers to step safely, free from the risk of slips or falls.

Which one will you be trying out first? Check out other waterproof, or winter boots in our online collection, or visit us in store to find your next pair. Stay warm Ontario! 

Leave a comment

Please note, comments must be approved before they are published

Download our app for 15% OFF your first mobile order >
*If applicable, the customer is responsible for all taxes, duties and brokerage fees upon import


Congratulations! Your order qualifies for free shipping You are €150,00 EUR away from free shipping. Canadian orders only. Exceptions apply*
No more products available for purchase