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What is better than cool and casual kicks Just your little tot when they're wearing this Oshima chukka boot from Timberland! Perfect for every day wear, this little sneak has a soft leather upper with breathable mesh panels, an easy hook and loop clo

These rugged chukkas are durable and stylish. High quality leather holds up to wear and tear, and a rubber lug outsole keeps your feet steady over varied terrain.

Timberland's Baxby Chukka is one smart shoe. Featuring Smart Comfort technology with supreme shock absorption, you'll make the most out of every step. Full traction allows you to get a grip on any surface, but the leather overlays and sleek fabric up

Over twenty five years ago, with the finest leathers and genuine New England craftsmanship, Timberland introduced its first waterproof leather boot. Rugged and dependable, it's the inspiration for our entire Classic series. Premium full grain waterpr

Timberland's Earthkeepers™ range features tough, rugged footwear made with the environment in mind. Thanks to moisture wicking linings made from recycled materials, organic cotton content, rugged outsoles made with Green Rubber™ material and the

This smart casual chukka has a stylish, confident look that's perfect for days at the office and nights on the town. The sleek silhouette and smooth leather uppers give it that premium look, while the subtle sporty influence keeps it fresh and modern

The Timberland Barentsburg Chukka tackles rugged comfort in style. This waterproof chukka is ready for you next great adventure. Features Premium waterproof leather for comfort and durability Smart ComfortR Biorhythmic chassis for comfort and durabi

The ultimate in easy going comfort with a conscience. Our EarthkeepersTM boots are original, rugged boots with a smaller environmental footprint than other shoes have. Timberland durability combined with lightweight versatility, outsoles made with re

This handsome boot from Timberland will lend a preppy step to his stride with its slotted cording design and intricate details. While this shoe is definitely all about keeping him in a casual cool style, its rubber sole will give him all the sure foo