Canada EN
Timberland Canada Home
Timberland Canada Home
Cart - 0 items

Chukkas & Chelseas

18 Products

18 Products

Mens Redwood Falls Waterproof Chukka Boot TBL Wheat HERO
Mens Redwood Falls Waterproof Chukka Boot TBL Wheat HERO
Mens Redwood Falls Waterproof Chukka Boot TBL Wheat ALT2
Mens Redwood Falls Waterproof Chukka Boot TBL Wheat ALT3
Mens Redwood Falls Waterproof Chukka Boot TBL Wheat ALT4
Mens Redwood Falls Waterproof Chukka Boot TBL Wheat ALT5
Mens Redwood Falls Waterproof Chukka Boot TBL Wheat ALT6
Mens Redwood Falls Waterproof Chukka Boot TBL Wheat ALT7
Slide 1 of 0
Extra 30% Off In Cart!
Men's Redwood Falls Waterproof Chukka Boot2 colours
CAD 155.00
Mens Redwood Falls Waterproof Chukka Boot TBL Soil Brushed FullGrain HERO
Mens Redwood Falls Waterproof Chukka Boot TBL Soil Brushed FullGrain HERO
Mens Redwood Falls Waterproof Chukka Boot TBL Soil Brushed FullGrain ALT2
Mens Redwood Falls Waterproof Chukka Boot TBL Soil Brushed FullGrain ALT3
Mens Redwood Falls Waterproof Chukka Boot TBL Soil Brushed FullGrain ALT4
Mens Redwood Falls Waterproof Chukka Boot TBL Soil Brushed FullGrain ALT5
Mens Redwood Falls Waterproof Chukka Boot TBL Soil Brushed FullGrain ALT6
Mens Redwood Falls Waterproof Chukka Boot TBL Soil Brushed FullGrain ALT7
Slide 1 of 0
Extra 30% Off In Cart!
Men's Redwood Falls Waterproof Chukka Boot2 colours
CAD 155.00
Mens Britton Road Waterproof Chukka Boot TBL Black FullGrain HERO
Mens Britton Road Waterproof Chukka Boot TBL Black FullGrain HERO
Mens Britton Road Waterproof Chukka Boot TBL Black FullGrain ALT2
Mens Britton Road Waterproof Chukka Boot TBL Black FullGrain ALT3
Mens Britton Road Waterproof Chukka Boot TBL Black FullGrain ALT4
Mens Britton Road Waterproof Chukka Boot TBL Black FullGrain ALT5
Mens Britton Road Waterproof Chukka Boot TBL Black FullGrain ALT6
Mens Britton Road Waterproof Chukka Boot TBL Black FullGrain ALT7
Slide 1 of 0
Extended Sizes
Men's Britton Road Waterproof Chukka Boot3 colours
CAD 170.00
Mens Redwood Falls Chelsea Boot TBL Black Brushed FullGrain HERO
Mens Redwood Falls Chelsea Boot TBL Black Brushed FullGrain HERO
Mens Redwood Falls Chelsea Boot TBL Black Brushed FullGrain ALT2
Mens Redwood Falls Chelsea Boot TBL Black Brushed FullGrain ALT3
Mens Redwood Falls Chelsea Boot TBL Black Brushed FullGrain ALT4
Mens Redwood Falls Chelsea Boot TBL Black Brushed FullGrain ALT5
Mens Redwood Falls Chelsea Boot TBL Black Brushed FullGrain ALT6
Mens Redwood Falls Chelsea Boot TBL Black Brushed FullGrain ALT7
Slide 1 of 0
Extra 30% Off In Cart!
Men's Redwood Falls Chelsea Boot2 colours
CAD 180.00
Mens Timberland Redwood Edge Essential Chukka Boot TBL Brown FullGrain HERO
Mens Timberland Redwood Edge Essential Chukka Boot TBL Brown FullGrain HERO
Mens Timberland Redwood Edge Essential Chukka Boot TBL Brown FullGrain ALTA
Mens Timberland Redwood Edge Essential Chukka Boot TBL Brown FullGrain ALT2
Mens Timberland Redwood Edge Essential Chukka Boot TBL Brown FullGrain ALT3
Mens Timberland Redwood Edge Essential Chukka Boot TBL Brown FullGrain ALT4
Mens Timberland Redwood Edge Essential Chukka Boot TBL Brown FullGrain ALT5
Mens Timberland Redwood Edge Essential Chukka Boot TBL Brown FullGrain ALT6
Mens Timberland Redwood Edge Essential Chukka Boot TBL Brown FullGrain ALTC
Mens Timberland Redwood Edge Essential Chukka Boot TBL Brown FullGrain ALT7
Mens Timberland Redwood Edge Essential Chukka Boot TBL Brown FullGrain ALTB
Slide 1 of 0
Extra 30% Off In Cart!
Men's Timberland® Redwood Edge Essential Chukka Boot2 colours
CAD 175.00
Mens Britton Road Chelsea Boot TBL Rust FullGrain HERO
Mens Britton Road Chelsea Boot TBL Rust FullGrain HERO
Mens Britton Road Chelsea Boot TBL Rust FullGrain ALT2
Mens Britton Road Chelsea Boot TBL Rust FullGrain ALT3
Mens Britton Road Chelsea Boot TBL Rust FullGrain ALT4
Mens Britton Road Chelsea Boot TBL Rust FullGrain ALT5
Mens Britton Road Chelsea Boot TBL Rust FullGrain ALT6
Mens Britton Road Chelsea Boot TBL Rust FullGrain ALT7
Slide 1 of 0
Men's Britton Road Chelsea Boot2 colours
CAD 170.00
Mens Britton Road Mid Waterproof Chukka Boot TBL Rust FullGrain HERO
Mens Britton Road Mid Waterproof Chukka Boot TBL Rust FullGrain HERO
Mens Britton Road Mid Waterproof Chukka Boot TBL Rust FullGrain ALT2
Mens Britton Road Mid Waterproof Chukka Boot TBL Rust FullGrain ALT3
Mens Britton Road Mid Waterproof Chukka Boot TBL Rust FullGrain ALT4
Mens Britton Road Mid Waterproof Chukka Boot TBL Rust FullGrain ALT5
Mens Britton Road Mid Waterproof Chukka Boot TBL Rust FullGrain ALT6
Mens Britton Road Mid Waterproof Chukka Boot TBL Rust FullGrain ALT7
Slide 1 of 0
Extended Sizes
Men's Britton Road Mid Waterproof Chukka Boot3 colours
CAD 170.00
Mens Timberland Redwood Edge Essential Chukka Boot TBL Dark Brown FullGrain HERO
Mens Timberland Redwood Edge Essential Chukka Boot TBL Dark Brown FullGrain HERO
Mens Timberland Redwood Edge Essential Chukka Boot TBL Dark Brown FullGrain ALT2
Mens Timberland Redwood Edge Essential Chukka Boot TBL Dark Brown FullGrain ALT3
Mens Timberland Redwood Edge Essential Chukka Boot TBL Dark Brown FullGrain ALT4
Mens Timberland Redwood Edge Essential Chukka Boot TBL Dark Brown FullGrain ALT5
Mens Timberland Redwood Edge Essential Chukka Boot TBL Dark Brown FullGrain ALT6
Mens Timberland Redwood Edge Essential Chukka Boot TBL Dark Brown FullGrain ALT7
Slide 1 of 0
Extra 30% Off In Cart!
Men's Timberland® Redwood Edge Essential Chukka Boot2 colours
CAD 175.00
Mens Timberland Road Trip Premium Mid Waterproof Chukka Boot TBL Rust FullGrainDark Grey HERO
Mens Timberland Road Trip Premium Mid Waterproof Chukka Boot TBL Rust FullGrainDark Grey HERO
Mens Timberland Road Trip Premium Mid Waterproof Chukka Boot TBL Rust FullGrainDark Grey ALT2
Mens Timberland Road Trip Premium Mid Waterproof Chukka Boot TBL Rust FullGrainDark Grey ALT3
Mens Timberland Road Trip Premium Mid Waterproof Chukka Boot TBL Rust FullGrainDark Grey ALT4
Mens Timberland Road Trip Premium Mid Waterproof Chukka Boot TBL Rust FullGrainDark Grey ALT5
Mens Timberland Road Trip Premium Mid Waterproof Chukka Boot TBL Rust FullGrainDark Grey ALT6
Mens Timberland Road Trip Premium Mid Waterproof Chukka Boot TBL Rust FullGrainDark Grey ALT7
Mens Timberland Road Trip Premium Mid Waterproof Chukka Boot TBL Rust FullGrainDark Grey ALT10
Mens Timberland Road Trip Premium Mid Waterproof Chukka Boot TBL Rust FullGrainDark Grey ALT11
Slide 1 of 0
Extra 30% Off In Cart!
Men's Timberland® Road Trip Premium Mid Waterproof Chukka Boot1 colour
CAD 180.00
Mens Redwood Edge Chelsea Boot TBL Black FullGrain HERO
Mens Redwood Edge Chelsea Boot TBL Black FullGrain HERO
Mens Redwood Edge Chelsea Boot TBL Black FullGrain ALT2
Mens Redwood Edge Chelsea Boot TBL Black FullGrain ALT3
Mens Redwood Edge Chelsea Boot TBL Black FullGrain ALT4
Mens Redwood Edge Chelsea Boot TBL Black FullGrain ALT5
Mens Redwood Edge Chelsea Boot TBL Black FullGrain ALT6
Mens Redwood Edge Chelsea Boot TBL Black FullGrain ALT7
Slide 1 of 0
Extra 30% Off In Cart!
Men's Redwood Edge Chelsea Boot2 colours
CAD 175.00
Mens Redwood Edge Chelsea Boot TBL Brown FullGrain HERO
Mens Redwood Edge Chelsea Boot TBL Brown FullGrain HERO
Mens Redwood Edge Chelsea Boot TBL Brown FullGrain ALT2
Mens Redwood Edge Chelsea Boot TBL Brown FullGrain ALT3
Mens Redwood Edge Chelsea Boot TBL Brown FullGrain ALT4
Mens Redwood Edge Chelsea Boot TBL Brown FullGrain ALT5
Mens Redwood Edge Chelsea Boot TBL Brown FullGrain ALT6
Mens Redwood Edge Chelsea Boot TBL Brown FullGrain ALT7
Slide 1 of 0
Extra 30% Off In Cart!
Men's Redwood Edge Chelsea Boot2 colours
CAD 175.00
Mens Britton Road Waterproof Chukka Boot TBL Brown Nubuck HERO
Mens Britton Road Waterproof Chukka Boot TBL Brown Nubuck HERO
Mens Britton Road Waterproof Chukka Boot TBL Brown Nubuck ALT2
Mens Britton Road Waterproof Chukka Boot TBL Brown Nubuck ALT3
Mens Britton Road Waterproof Chukka Boot TBL Brown Nubuck ALT4
Mens Britton Road Waterproof Chukka Boot TBL Brown Nubuck ALT5
Mens Britton Road Waterproof Chukka Boot TBL Brown Nubuck ALT6
Mens Britton Road Waterproof Chukka Boot TBL Brown Nubuck ALT7
Slide 1 of 0
Men's Britton Road Waterproof Chukka Boot3 colours
CAD 170.00

Viewing 18 of 18 Products