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| Best Seller  | Men's Timberland Davis Square Chukka Boot - Brown - Casual boots Elevate your casual wardrobe with the Davis Square chukka boot from Timberland. The plush trim on the collar lend a cozy touch, while the Defender Repellent Systems treatment deters... more | $84.99 $67.98 go to store |
 | Timberland Davis Square Leather/Fabric Boot - Mens 8 Black Boot Medium *This boot is ready to treat your feet to comfort and style! *Better Leather/ReBOTL™ fabric upper *Padded collar for added comfort *Breathable mesh lining *OrthoLite® cushioned footbed *Rubber sole more | $104.95 $41.97 FREE shipping go to store |
| Best Seller  | Timberland Davis Square Leather/Fabric Boot - Mens 7 Tan Boot Medium *This boot is ready to treat your feet to comfort and style! *Better Leather/ReBOTL™ fabric upper *Padded collar for added comfort *Breathable mesh lining *OrthoLite® cushioned footbed *Rubber sole more | $104.95 $41.97 FREE shipping go to store |
 | Timberland Davis Square Leather/Fabric Boot - Mens 9 Black Boot Medium *This boot is ready to treat your feet to comfort and style! *Better Leather/ReBOTL™ fabric upper *Padded collar for added comfort *Breathable mesh lining *OrthoLite® cushioned footbed *Rubber sole more | $104.95 $41.97 FREE shipping go to store |
 | Men's Timberland Maple Grove Chukka Boot - White - Casual boots Sporty yet refined, this leather chukka boot is one you can feel good about, with a lining made partially from post-consumer plastic bottles. more | FREE shipping go to store |
 | Men's Timberland Maple Grove Chukka Boot - Black - Casual boots Sporty yet refined, this leather chukka sneaker is one you can feel good about, with a lining made partially from post-consumer plastic bottles. more | FREE shipping go to store |
 | Killington Chukka Boots - Black - Timberland Boots Men's Timberland Killington Chukka Boots - Black - Casual boots Men's Timberland boots with premium full-grain leather uppers from a Leather Working Group Silver-rated sustainable tannery. Showcasing an iconic, chukka boot silhouette, the lightweight,... more | $170.00 $86.00 go to store |
 | Timberland Davis Square Leather/Fabric Boot - Mens 8 Brown Boot Medium *This boot is ready to treat your feet to comfort and style! *Better Leather/ReBOTL™ fabric upper *Padded collar for added comfort *Breathable mesh lining *OrthoLite® cushioned footbed *Rubber sole more | $104.95 $49.97 FREE shipping go to store |
 | Timberland Davis Square Leather/Fabric Boot - Mens 8.5 Tan Boot Medium *This boot is ready to treat your feet to comfort and style! *Better Leather/ReBOTL™ fabric upper *Padded collar for added comfort *Breathable mesh lining *OrthoLite® cushioned footbed *Rubber sole more | $104.95 $41.97 FREE shipping go to store |
 | Timberland Davis Square Leather/Fabric Boot - Mens 8 Tan Boot Medium *This boot is ready to treat your feet to comfort and style! *Better Leather/ReBOTL™ fabric upper *Padded collar for added comfort *Breathable mesh lining *OrthoLite® cushioned footbed *Rubber sole more | $104.95 $41.97 FREE shipping go to store |
 | Timberland Davis Square Leather/Fabric Boot - Mens 7.5 Brown Boot Medium *This boot is ready to treat your feet to comfort and style! *Better Leather/ReBOTL™ fabric upper *Padded collar for added comfort *Breathable mesh lining *OrthoLite® cushioned footbed *Rubber sole more | $104.95 $49.97 FREE shipping go to store |
 | Timberland Davis Square Leather/Fabric Boot - Mens 9 Tan Boot Medium *This boot is ready to treat your feet to comfort and style! *Better Leather/ReBOTL™ fabric upper *Padded collar for added comfort *Breathable mesh lining *OrthoLite® cushioned footbed *Rubber sole more | $104.95 $41.97 FREE shipping go to store |
 | Timberland Davis Square Leather/Fabric Boot - Mens 9 Brown Boot Medium *This boot is ready to treat your feet to comfort and style! *Better Leather/ReBOTL™ fabric upper *Padded collar for added comfort *Breathable mesh lining *OrthoLite® cushioned footbed *Rubber sole more | $104.95 $49.97 FREE shipping go to store |
 | Timberland Davis Square Leather/Fabric Boot - Mens 7 Black Boot Medium *This boot is ready to treat your feet to comfort and style! *Better Leather/ReBOTL™ fabric upper *Padded collar for added comfort *Breathable mesh lining *OrthoLite® cushioned footbed *Rubber sole more | $104.95 $41.97 FREE shipping go to store |
 | Timberland Davis Square Leather/Fabric Boot - Mens 7.5 Black Boot Medium *This boot is ready to treat your feet to comfort and style! *Better Leather/ReBOTL™ fabric upper *Padded collar for added comfort *Breathable mesh lining *OrthoLite® cushioned footbed *Rubber sole more | $104.95 $41.97 FREE shipping go to store |
 | Timberland Davis Square Leather/Fabric Boot - Mens 8.5 Black Boot Medium *This boot is ready to treat your feet to comfort and style! *Better Leather/ReBOTL™ fabric upper *Padded collar for added comfort *Breathable mesh lining *OrthoLite® cushioned footbed *Rubber sole more | $104.95 $41.97 FREE shipping go to store |
 | Timberland Davis Square Leather/Fabric Boot - Mens 8.5 Brown Boot Medium *This boot is ready to treat your feet to comfort and style! *Better Leather/ReBOTL™ fabric upper *Padded collar for added comfort *Breathable mesh lining *OrthoLite® cushioned footbed *Rubber sole more | $104.95 $49.97 FREE shipping go to store |
 | Timberland Maple Grove Fabric/Leather Chukka - Mens 8 Tan Boot Medium *Fabric/leather chukka from Timberland *Upper is made with leather sourced from farms that use regenerative agriculture practices *ReBOTL fabric lining *Lightly cushioned footbed *Rubber midsole *Rubber outsoles from farms committed to regenerative... more | $129.95 $116.97 FREE shipping go to store |
 | Tbl® 1973 Newman Waterproof Chukka Boot Men's Timberland Tbl® 1973 Newman Waterproof Chukka Boot - Black - Casual boots Inspired by the original iconic boot, this durable chukka boasts seam-sealed waterproof protection, a padded collar, arch-supporting shank and grippy lug sole. The leather... more | FREE shipping go to store |
 | 1973 Newman Premium Mid Chukka Boot Men's Timberland 1973 Newman Premium Mid Chukka Boot - Black - Casual boots Get impressive style and protection in the Timberland 1973 Newman Premium Mid chukka boot. Crafted with waterproof Premium Timberland leather upper and seam-sealed design, this... more | FREE shipping go to store |
 | Timberland Atwells Ave WP Chukka - Mens 10 Tan Boot Medium *Chukka boot from Timberland *Waterproof Better Leather upper *Seam-sealed construction *Lace-up front closure *EVA comfort footbed *Compression-molded EVA outsole more | $144.95 $130.97 FREE shipping go to store |
 | Timberland Ashwood Park Warm Lined Chukka - Mens 11.5 Black Boot Medium *Chukka boot from Timberland *Better Leather upper *Teddy fleece lining in collar and tongue *Lace-up front closure *OrthoLite comfort footbed *Rubber lug outsole more | $99.95 $88.97 FREE shipping go to store |
 | Timberland Atwells Ave WP Chukka - Mens 7.5 Tan Boot Medium *Chukka boot from Timberland *Waterproof Better Leather upper *Seam-sealed construction *Lace-up front closure *EVA comfort footbed *Compression-molded EVA outsole more | $144.95 $130.97 FREE shipping go to store |
 | Timberland Men's Premium Chukka - 8.5 Black Boot Medium *Whatever the weather outside, the forecast inside this boot is dry and comfortable *Seam-sealed waterproof nubuck leather upper *Cambrelle® fabric lining wicks away foot moisture *Collar, tongue, and insole are cushioned to soften every step *Durable... more | FREE shipping go to store |
 | Timberland Maple Grove Chukka - Mens 9.5 Tan Boot Medium *Take on your day with this eco-friendly chukka boot! *Upper made with Better Leather from an LWG Silver-rated tannery *Lace-up closure *ReBOTL fabric lining *Rubber midsole *55% rubber outsole from farms committed to regenerative agriculture more | FREE shipping go to store |
 | Timberland Maple Grove Chukka - Mens 11 Tan Boot Medium *Take on your day with this eco-friendly chukka boot! *Upper made with Better Leather from an LWG Silver-rated tannery *Lace-up closure *ReBOTL fabric lining *Rubber midsole *55% rubber outsole from farms committed to regenerative agriculture more | FREE shipping go to store |
 | Timberland Redwood Falls Waterproof Chukka - Mens 8 Brown Boot Medium *Premium leather upper with TimberDry waterproof membrane *Rustproof speedlace hardware with lace hooks at top *Ankle-high shaft *Tie closure *ReBOTL fabric lining *Ortholite footbed *EVA midsole *Griptstick rubber outsole with patented L7 lug design more | FREE shipping go to store |
 | Timberland Atwells Ave WP Chukka - Mens 11 Black Boot Medium *Chukka boot from Timberland *Waterproof Better Leather upper *Seam-sealed construction *Lace-up front closure *EVA comfort footbed *Compression-molded EVA outsole more | FREE shipping go to store |
 | Timberland Atwells Ave WP Chukka - Mens 10 Black Boot Medium *Chukka boot from Timberland *Waterproof Better Leather upper *Seam-sealed construction *Lace-up front closure *EVA comfort footbed *Compression-molded EVA outsole more | FREE shipping go to store |
 | Timberland Atwells Ave WP Chukka - Mens 9.5 Tan Boot Medium *Chukka boot from Timberland *Waterproof Better Leather upper *Seam-sealed construction *Lace-up front closure *EVA comfort footbed *Compression-molded EVA outsole more | $144.95 $130.97 FREE shipping go to store |
 | Timberland Arbor Road Waterproof Chukka - Mens 7 Black Boot Medium *Chukka boot from Timberland *Premium Timberland leather upper *Lace-up front closure *ReBOTL fabric lining *OrthoLite® footbed *Compression-molded EVA midsole *Seam-sealed construction *GreenStride sole *Rubber outsole more | $169.95 $152.97 FREE shipping go to store |
 | Timberland Arbor Road Waterproof Chukka - Mens 7.5 Black Boot Medium *Chukka boot from Timberland *Premium Timberland leather upper *Lace-up front closure *ReBOTL fabric lining *OrthoLite® footbed *Compression-molded EVA midsole *Seam-sealed construction *GreenStride sole *Rubber outsole more | $169.95 $152.97 FREE shipping go to store |
 | Timberland Men's Premium Chukka - 7.5 Black Boot Medium *Whatever the weather outside, the forecast inside this boot is dry and comfortable *Seam-sealed waterproof nubuck leather upper *Cambrelle® fabric lining wicks away foot moisture *Collar, tongue, and insole are cushioned to soften every step *Durable... more | FREE shipping go to store |
 | Timberland Maple Grove Chukka - Mens 7 Black Boot Medium *Take on your day with this eco-friendly chukka boot! *Upper made with Better Leather from an LWG Silver-rated tannery *Lace-up closure *ReBOTL fabric lining *Rubber midsole *55% rubber outsole from farms committed to regenerative agriculture more | FREE shipping go to store |
 | Timberland Arbor Road Waterproof Chukka - Mens 9 Black Boot Medium *Chukka boot from Timberland *Premium Timberland leather upper *Lace-up front closure *ReBOTL fabric lining *OrthoLite® footbed *Compression-molded EVA midsole *Seam-sealed construction *GreenStride sole *Rubber outsole more | $169.95 $152.97 FREE shipping go to store |
 | Timberland Redwood Falls Waterproof Chukka - Mens 10 Brown Boot Medium *Premium leather upper with TimberDry waterproof membrane *Rustproof speedlace hardware with lace hooks at top *Ankle-high shaft *Tie closure *ReBOTL fabric lining *Ortholite footbed *EVA midsole *Griptstick rubber outsole with patented L7 lug design more | FREE shipping go to store |
 | Timberland Arbor Road Waterproof Chukka - Mens 11.5 Brown Boot Medium *Chukka boot from Timberland *Premium Timberland leather upper *Lace-up front closure *ReBOTL fabric lining *OrthoLite® footbed *Compression-molded EVA midsole *Seam-sealed construction *GreenStride sole *Rubber outsole more | $169.95 $135.97 FREE shipping go to store |
 | Timberland Maple Grove Chukka - Mens 12 Tan Boot Medium *Take on your day with this eco-friendly chukka boot! *Upper made with Better Leather from an LWG Silver-rated tannery *Lace-up closure *ReBOTL fabric lining *Rubber midsole *55% rubber outsole from farms committed to regenerative agriculture more | FREE shipping go to store |
 | Timberland Maple Grove Chukka - Mens 9.5 Black Boot Medium *Take on your day with this eco-friendly chukka boot! *Upper made with Better Leather from an LWG Silver-rated tannery *Lace-up closure *ReBOTL fabric lining *Rubber midsole *55% rubber outsole from farms committed to regenerative agriculture more | FREE shipping go to store |
 | Timberland Redwood Falls Waterproof Chukka - Mens 8.5 Brown Boot Medium *Premium leather upper with TimberDry waterproof membrane *Rustproof speedlace hardware with lace hooks at top *Ankle-high shaft *Tie closure *ReBOTL fabric lining *Ortholite footbed *EVA midsole *Griptstick rubber outsole with patented L7 lug design more | FREE shipping go to store |
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