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Shoes - Men's shoes


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Leather military boots Can$195.00 Can$99.95
Editor's pick
Absolute boots Can$150.00 Can$99.95
Steve Madden
Felderr chelsea boots Can$135.00 Can$99.95
Steve Madden
Felderr chelsea boots Can$135.00 Can$99.95
Steve Madden
Originals 1460 boots
Dr. Martens
Military boots Can$745.00
Combat boots Can$600.00
Sneaker boots Can$195.00
Le 31
Chelsea zip boots Can$325.00
Suede zipped boots Can$550.00
The Kooples
Smooth leather zipped boots Can$550.00
The Kooples
Repel shoe protector Can$24.00
Jason Markk
Biodegradable shoe cleaner Can$24.00
Jason Markk

Men's boots from Simons

As the cold weather rolls in, your footwear needs could change on a dime. That’s why every man should have a quality pair of boots in his closet. Luckily, Simons stocks a range of men’s boots that are both stylish and functional. Not only will they keep your feet warm and dry through the rain, slush and snow, but they’ll look great on the hiking trail or paired with jeans when you head out for Sunday brunch. Browse through our selection and pick out a pair or two that reflects your style and guarantees you’ll make it through the winter with as few soakers as possible.  

Stay warm and on-trend

Depending on where you live, the winter months might call for a pair of rubber, waterproof boots. Autumn, on the other hand, is the perfect time for a stylish pair of suede chelsea boots. Wear them to work, out on a date, or to a farmer’s market to make a strong statement with your low-key, timeless sense of style. Don’t forget to stock up on shoe protector and shoe cleaner to make sure your boots make it through the season sans salt stains and continue to be that wardrobe staple you need them to be for years to come. 

Brands you love

With a range of styles from different brands available, Simons has something for everyone. Prevent slips on icy sidewalks with a pair of lace up Timberlands or SORELs, or for a classic look opt for Dr. Martens Original 1460 boots. For a quality pair of chelsea boots to polish off your look, you can’t go wrong with Hudson, Steve Madden, or Hugo. If you’re looking for a pair of unique designer boots to invest in, Emporio Armani, DSquared2, and Paul Smith make footwear with high-end materials, expert construction, and finishing touches that will make sure your boots make a statement.  


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