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| Best Seller  | Timberland Ashwood Park Warm Lined Chukka - Mens 12 Tan 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
Timberland Ashwood Park Warm Lined Chukka - Mens 12 Tan 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 | $99.95 $89.97 FREE shipping go to store |
 | Timberland Ashwood Park Warm Lined Chukka - Mens 11.5 Tan 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
Timberland Ashwood Park Warm Lined Chukka - Mens 11.5 Tan 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 | $99.95 $89.97 FREE shipping go to store |
| Best Seller  | Blair Men's Totes® Insulated Side-Zip Boots - Black - 9 - Medium It's all here: every detail to keep your feet warm and your steps sure, all winter long. Totes items are not eligible for additional discounts or special promotions. • Water-repellent synthetic upper • Fully lined in polyester faux fur • Thermolite®... ... more | go to store |
 | Winsor Park Chukka - Black - Timberland Boots Men's Timberland Winsor Park Chukka - Black - Casual boots By purchasing this product, you are supporting the responsible manufacturing of leather through the Leather Working Group. ... more | $190.00 $95.00 go to store |
 | Blair Men's Totes® Insulated Side-Zip Boots - Black - 10 - Medium It's all here: every detail to keep your feet warm and your steps sure, all winter long. Totes items are not eligible for additional discounts or special promotions. • Water-repellent synthetic upper • Fully lined in polyester faux fur • Thermolite®... ... more | go to store |
 | Blair Men's Totes® Insulated Side-Zip Boots - Black - 13 - Medium It's all here: every detail to keep your feet warm and your steps sure, all winter long. Totes items are not eligible for additional discounts or special promotions. • Water-repellent synthetic upper • Fully lined in polyester faux fur • Thermolite®... ... more | go to store |
 | Condition: New With Box Color: Coyote Material: Lightweight Canvas Width: Medium Features: Lightweight Canvas Upper Breathable Fastdry Lining Insite Technology Footbed Ensures Lasting Comfort Carhartt Lwd Midsole Delivers Elevated Lightweight Comfort... ... more | 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
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 | $99.95 $88.97 FREE shipping go to store |
 | Timberland Men's Premium Chukka - 10.5 Tan 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
Timberland Men's Premium Chukka - 10.5 Tan 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... | FREE shipping go to store |
 | Timberland Maple Grove Chukka - Mens 10 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
Timberland Maple Grove Chukka - Mens 10 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 | FREE shipping go to store |
 | Timberland Maple Grove Chukka - Mens 13 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
Timberland Maple Grove Chukka - Mens 13 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 | 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
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 | $144.95 $130.97 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
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 | FREE shipping go to store |
 | Timberland Maple Grove Chukka - Mens 7.5 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
Timberland Maple Grove Chukka - Mens 7.5 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 | FREE shipping go to store |
 | Timberland Men's Premium Chukka - 10 Tan 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
Timberland Men's Premium Chukka - 10 Tan 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... | 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
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 | $144.95 $130.97 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
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 | FREE shipping go to store |
 | Timberland Men's Premium Chukka - 7.5 Tan 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
Timberland Men's Premium Chukka - 7.5 Tan 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... | FREE shipping go to store |
 | Timberland Maple Grove Chukka - Mens 9 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
Timberland Maple Grove Chukka - Mens 9 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 | FREE shipping go to store |
 | Timberland Atwells Ave WP Chukka - Mens 8 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
Timberland Atwells Ave WP Chukka - Mens 8 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 | $144.95 $130.97 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
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 | $144.95 $130.97 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
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 | FREE shipping go to store |
 | Timberland Atwells Ave WP Chukka - Mens 11.5 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
Timberland Atwells Ave WP Chukka - Mens 11.5 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 | $144.95 $130.97 FREE shipping go to store |
 | Timberland Atwells Ave WP Chukka - Mens 8.5 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
Timberland Atwells Ave WP Chukka - Mens 8.5 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 | $144.95 $130.97 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
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... | $129.95 $116.97 FREE shipping go to store |
 | Timberland Maple Grove Chukka - Mens 11.5 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
Timberland Maple Grove Chukka - Mens 11.5 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 | FREE shipping go to store |
 | Timberland Maple Grove Chukka - Mens 8.5 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
Timberland Maple Grove Chukka - Mens 8.5 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 | FREE shipping go to store |
 | Timberland Maple Grove Chukka - Mens 8 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
Timberland Maple Grove Chukka - Mens 8 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 | FREE shipping go to store |
 | Timberland Maple Grove Chukka - Mens 7 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
Timberland Maple Grove Chukka - Mens 7 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 | FREE shipping go to store |
 | Timberland Maple Grove Chukka - Mens 10.5 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
Timberland Maple Grove Chukka - Mens 10.5 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 | FREE shipping go to store |
 | Timberland Atwells Ave WP Chukka - Mens 11 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
Timberland Atwells Ave WP Chukka - Mens 11 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 | $144.95 $130.97 FREE shipping go to store |
 | Timberland TBL Originals Ultra Waterproof Mid - Mens 7.5 Tan Boot Medium *Outdoor boot from Timberland *Waterproof premium Timberland leather upper *Padded collar *Lace-up front *TimberDry waterproof membrane *ReBOTL fabric lining *OrthoLite® footbed *Compression molded EVA midsole *GreenStride sole *Rubber lug outsole ... more
Timberland TBL Originals Ultra Waterproof Mid - Mens 7.5 Tan Boot Medium *Outdoor boot from Timberland *Waterproof premium Timberland leather upper *Padded collar *Lace-up front *TimberDry waterproof membrane *ReBOTL fabric lining *OrthoLite® footbed *Compression molded EVA midsole *GreenStride sole *Rubber lug outsole | $164.95 $148.97 FREE shipping go to store |
 | Timberland Arbor Road Waterproof Chukka - Mens 10.5 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
Timberland Arbor Road Waterproof Chukka - Mens 10.5 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 | $169.95 $152.97 FREE shipping go to store |
 | Timberland Men's Premium Chukka - 7 Brown 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
Timberland Men's Premium Chukka - 7 Brown 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... | FREE shipping go to store |
 | Timberland Maple Grove Chukka - Mens 8 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
Timberland Maple Grove Chukka - Mens 8 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 | FREE shipping go to store |
 | Timberland Arbor Road Waterproof Chukka - Mens 8.5 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
Timberland Arbor Road Waterproof Chukka - Mens 8.5 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 | $169.95 $135.97 FREE shipping go to store |
 | Timberland Arbor Road Waterproof Chukka - Mens 9.5 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
Timberland Arbor Road Waterproof Chukka - Mens 9.5 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 | $169.95 $135.97 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
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... | FREE shipping go to store |
 | Timberland Maple Grove Chukka - Mens 9 Brown 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
Timberland Maple Grove Chukka - Mens 9 Brown 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 | $124.95 $111.97 FREE shipping go to store |
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