Chukkas & Chelseas

Our men's chukka boots combine the sturdy resilience of a classic Timberland shoe with versatile designs that suit a wide range of occasions. 

From premium Timberland® leather to EVA footbeds and tough rubber lug outsoles, our men's chukka boots are constructed with durability and comfort in mind. 

If you're looking for a smart-casual shoe for work or a go-to boot for daily wear, rest assured that our chukka boots will keep you comfortable and protected no matter what the elements throw your way.

For a relaxed and casual look, take a look at our Men's Maple Grove Leather Chukka. Available in seven different colours and designs, these sporty chukka boots for men are built for everyday wear. With a classic yet versatile sneaker boot aesthetic, you can pair these boots with a wide range of men's pants to create a timeless, casual, and effortlessly cool look.

Opt for the Men's Arbor Road Waterproof Chukka for a sleeker design with equal durability and practicality. Robust, rugged, and waterproof, these chukka boots will keep you comfortable and protected in all kinds of weather. You can find these chukka boots in brown, black, and wheat full-grain. They come with seam-sealed construction that makes them extra water-resistant.

Are you looking for something more sophisticated for smart-casual events and social occasions? Take a look at our Men's Redwood Falls Waterproof Chukka Boot. Designed with Gripstick™ rubber outsoles, OrthoLite® footbeds, and EVA midsoles, these men's chukka boots are as durable as they are stylish. You can dress these versatile chukkas up or down as needed. With a choice of three colours, you can find this elegant boot in a shade that works for your style and wardrobe.

For a pair of waterproof boots that function as work boots and as dress boots, try the Men's GreenStride™ Atwells Ave Waterproof Chukka Boot. Made with waterproof leather, EVA compression-moulded outsoles and footbeds, and a GreenStride™ responsibly sourced rubber sole, these tough, lace-up ankle boots will keep you comfy and stylish in a variety of settings.

Browse our wide range of men's chukka boots online now to find the perfect pair for your needs. For more style inspiration, check out our new arrivals.

For discounted prices and exclusive offers, take a look at our sale selection before you checkout. 

Buy your new favourite boots online today. Or, if you prefer to try before you buy, use our store locator to find your nearest retailer selling men’s, women’s and kids’ winter boots, hiking boots, dress shoes, loafers, and slip-ons.