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 …

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Styled to reflect the legendary bold look of our iconic Timberland® boot, the Arbor Road chukka features with a ReBOTL™ lining containing at least 50% recycled plastic. Plus, you’ll enjoy the natural comfort of our GreenStride™ insole with foam made using an EVA blend including 75% biobased materials derived from sugar cane and ...

Whether you’re looking for men’s work boots or men’s boots, Timberland has all sorts of men’s footwear for your personal style. Our Men’s Arbor Road Waterproof Chukka is the go-to choice for a relaxed yet elevated look you can dress up or down with a range of work and casual outfits.

Feel the freedom that comes when you're ready for any adventure! You'll find everything you need in our waterproof Chukka boot. Styled to reflect the legendary bold look of our iconic Timberland® boot, this one also features a ReBOTL™ fabric lining containing at least 50% recycled plastic.

Hit the trails with the exceptional traction of the Redwood Falls Chukka boot. All-weather uppers made with waterproof Premium Timberland® Leather surround a ReBOTL™ fabric lining containing at least 50% recycled plastic.

Timberland's boots, clothing and outerwear feature iconic style, outdoor performance and eco-conscious innovation - built for bold adventures and hard work. New & Featured Footwear

Made to be super comfortable with our HoverLite™ comfort soles, these men's chukka boots feature the Defender Repellent Systems® treatment to help keep them looking like new. They also feature quality materials, like premium Timberland® leather uppers.

Take on the outdoors with Men's Westmore Boot featuring a Premium Timberland® leather upper. With 100% organically grown cotton laces, a comfy EVA footbed, and a rubber outsole, it’s as functional as it is stylish.The SensorFlex™ comfort system helps offer a three-layer comfort system built into the outsole that helps deliver support ...

This seam-sealed, durable, waterproof chukka features a padded collar, a fiberglass shank for arch support, and rubber lug outsoles for traction. By purchasing this product, you are supporting responsible manufacturing of leather through the Leather Working Group.