 $49.99
was $69.99, save $20.00
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You'll love the comfort and styleLeather upperPadded and comfortableLightweight and flexible. Timberland saddle oxford with perforation details and ultra comfortable styling. More details...
Black
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 $58.49
was $89.99, save $31.50
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Smooth, soft nubuck and suede combine in a lightweight approach inspired sporty casual oxford look, with colorful contrast stitching, multi overlay accents, and contrast web fabric strap detail.... More details...
Grey W/ Blue
Rust W/ Orange
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 $58.49
was $89.99, save $31.50
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Traction patterned outsole. When the classic boat shoe just isn't your style, you will love these sporty alternatives from Timberland. More details...
Red
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 $71.99
was $89.99, save $18.00
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Burn no calories tying on these clever Timberland Caliburn Laceless sneakers. Low profile midsole, flexible traction outsole. More details...
Grey Burnished
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 $63.99
was $79.99, save $16.00
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Full lace up front with metal eyelets, embossed Timberland logo detail. Padded collar and tongue, smooth lining, cushioned comfort insole. More details...
Brown Burnished
Black Burnished
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 $71.99
was $89.99, save $18.00
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Smooth leather upper in a low profile sporty casual sneaker style, with a rounded toe, stitching and overlay accents, and Timberland logo detail. Hiking inspired design, full lace up front,... More details...
Black
Cognac Smooth
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 $76.49
was $89.99, save $13.50
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Matte leather and breathable fabric upper in an adventure casual style, with stitching and perforation accents, abrasion-resistant toe and heel caps, daisy-chain lace up front, padded tongue with... More details...
Greige
Rust
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 $87.99
was $109.99, save $22.00
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Full lace up front, padded collar and tongue, smooth lining, cushioned comfort insole. Speak softly and walk comfortably wearing the Timberland Speke Oxford. More details...
Tan Tumbled
Taupe Oiled
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 $69.99
was $79.99, save $10.00
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The low-profile rubber sole is long-lasting, flexible and lightweight, and provides good tractionPremium leather upper, stretchy fabric inlays, contrast stitching, rugged leather toe bumperSmart... More details...
Brown
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 $69.99
was $79.99, save $10.00
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You’ll like the Annapolis so much you’ll consider wearing it even when no water is in sightLeather moccasin-style upper with contrast stitching, metal eyelets and leather lacing... More details...
Brown
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 $110.49
was $129.99, save $19.50
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Stitched topsole, lightweight, shock absorbing EVA midsole. Timberland makes this rugged casual easy to wear in wet weather. More details...
Brown
Tan
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 $69.99
was $89.99, save $20.00
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The Alpine Oxford is durable, stylish, cushioned and comfortable. This light hiker by Timberland will be there for you when your route entails city streets as well as hiking trails. More details...
Brown
Black
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 $58.49
was $89.99, save $31.50
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Smooth full grain leather upper in a sporty casual oxford look, with contrast colored scratch distressed suede wraparound mudguard overlays, contrast colored stitching accents, and a full lace up... More details...
Brown
Tan
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 $76.49
was $89.99, save $13.50
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Distressed textured and scratched leather combine in a stylish sporty casual oxford, with contrast colored stitching accents, overlays, perforated synthetic panels, and Timberland logo detail.... More details...
Taupe
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 $103.99
was $129.99, save $26.00
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Experience the rugged good looks of this airport-friendly casual from Timberland. Breathable leather lining. More details...
Tan
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 $84.99
was $99.99, save $15.00
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Envelop your feet in comfort with this rugged casual from Timberland. Smooth pig skin lining, cushioned Smart Comfort(R) supportive insole. More details...
Dark Brown Textured
Dark Green Textured
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 $84.99
was $99.99, save $15.00
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Four eyelet lace up front, flexible leather tongue, lightly padded collar. Uncover the brilliant comfort of this rugged casual from Timberland. More details...
Tan Tumbled
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 $76.49
was $89.99, save $13.50
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Smooth suede upper in a casual athletic oxford style, with a square toe, side and heel overlay accents, sporty side striping, and stitching and Timberland logo details. Cushioning Smart Comfort(R)... More details...
Brown On White
Green On White
Tan/Navy On White
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 $80.74
was $94.99, save $14.25
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Freedom and protection combine in this tough shoe from Timberland.Waterproof nubuck or leather upper in a technical hiking sandal style, with a closed toe, rubberized overlay, sueded fabric panels,... More details...
Dark Brown
Greige
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 $103.99
was $129.99, save $26.00
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PreciseFit(R) removable cushioned insole system adjusts for a perfect size and width. Comfort, fit and style come together in the Timberland Outlier City Oxford casual. More details...
Tan Smooth
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 $71.99
was $89.99, save $18.00
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Padded collar and tongue, smooth lining, cushioned insole. The new casual is sport infused, comfortable and relaxed, like the Timberland Scroll Sport sneaker. More details...
Dark Brown Suede
Black Suede
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 $71.99
was $89.99, save $18.00
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Smooth lining, cushioned comfort insole. Low slung midsole and a traction patterned outsole. More details...
Brown Burnished
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 $75.99
was $94.99, save $19.00
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Heel features a hint of Smartwool, fully lined in soft, moisture-wicking Smartwood fabric. Cushioned comfort insole, shock absorbing midsole. More details...
Dark Brown
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 $79.99
was $99.99, save $20.00
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Timberland offers sporty casual style and optimum comfort in its Bolden Oxford shoe. Soft dual toned leather upper with round toe, contrast double-stitching and freeform detailing, embroidered... More details...
Dark Brown
Tan Oiled
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 $99.99
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Because gym shoes should stay at the gym, the Timberland Palladian casual sneaker is ready to refine your style. Flexible traction outsole. More details...
Black Smooth
Dark Brown Smooth
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