 $110.49
was $129.99, save $19.50
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Black
Saddle Tan Smooth
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 $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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 $87.99
was $109.99, save $22.00
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Flexible midsole, traction patterned outsole. Two eyelet lace up front with logo embossed tongue flap, padded collar and tongue, smooth lining, cushioned comfort insole. More details...
Tan Tumbled
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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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 $67.99
was $79.99, save $12.00
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Built to handle the tides in stride, this 2-eye boat oxford combines sporty styling and signature Timberland quality and comfort. Flexible sporty midsole and a nonmarking deck style traction... More details...
Rootbeer Leather
Brown Oiled Leather
Navy
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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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 $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, suede and canvas moccasin-style upper with contrast stitching, metal eyelets and... More details...
Lt. 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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 $59.49
was $69.99, save $10.50
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Contrasting or coordinating stitched topsole, flexible, cushioning midsole and lug traction patterned outsole. Soft fabric lining, cushioned removable insole. More details...
Wheat
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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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 $93.49
was $109.99, save $16.50
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Traction patterned outsole, with a 1 inch heel. Three eyelet lace up front, flexible tongue. More details...
Brown
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 $110.49
was $129.99, save $19.50
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Polyurethane cushioning midsole. Traction patterned non-marking rubber outsole. More details...
Brown Burnished
Tan Burnished
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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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 $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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 $103.99
was $129.99, save $26.00
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Timberland's Oppland oxford will get you through the week in great comfort and styleWaterproof leather upperPadded collar and tongueSeam-sealed constructionAirport-friendly nylon support... More details...
Black Printed
Red/Brown Printed
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 $79.99
was $99.99, save $20.00
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Flexible traction patterned outsole, built in 3/4 inch heel. Smooth leather upper in a handsome casual dress slip on style, with a rounded toe, stitched center seam detail and wing tip style side... More details...
Black Smooth
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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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 $103.99
was $129.99, save $26.00
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Smooth full grain leather upper in a sporty casual driving style oxford, with a rounded toe, stitched seam accents dual side bicycle style seam detailing. Flexible midsole, traction patterned... More details...
Dark Brown Plush
Black
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 $103.99
was $129.99, save $26.00
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Flexible midsole, traction patterned outsole. Smooth full grain leather upper in a sporty casual driving style loafer, with a rounded toe, stitched seam accents and apron style overlay toe. More details...
Black
Saddle Tan
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 $69.99
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From yacht decks to patio decks, the Timberland Kia Wah Bay boat shoe is always in style. Padded collar, smooth lining, cushioned comfort insole. More details...
Light Brown
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 $79.99
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Smooth nubuck leather upper in a slip on boat style casual moc, with a stitched seam moc style toe, side stitching, seam and overlay detail, Timberland logo accents and side elastic panels for... More details...
Brown Nubuck
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 $99.99
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The classic penny loafer gets a laid back upgrade in these perfect Palladian Penny loafers by Timberland. Contrast stitching details, flared tongue and a penny loafer style instep strap cutout... More details...
Red Brown
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 $99.99
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These sturdy Luke Street Heavy Ox casuals will take you from casual day all the way through the weekend. Waterproof smooth leather upper in a casual oxford style with a round plain toe. More details...
Red Brown
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 $139.99
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Smooth full grain leather upper in a casual slip on style, with a rounded toe featuring rolled moc style seam detail, side stitching and seam accents, and dual side elastic panels for easy slip on... More details...
Brown Printed
Black Printed
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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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 $84.99
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Cinchable elastic instep cord with sliding lock. Cushioned comfort insole, flexible traction patterned outsole. More details...
Dark Brown
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 $129.99
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Smooth pig skin leather lining. Stitched topsole, lightweight, shock absorbing EVA midsole. More details...
Black
Tan
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 $104.99
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Dark Brown
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