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| Best Seller  | Timberland Ashwood Park Warm Lined Chukka - Mens 8.5 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 8.5 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 |
 | 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 |
| Best Seller  | Reebok Postal Express Chukka Boots - Men's Black 6 Medium 690774213616 Reebok Postal Express Chukka Boots - Men's Black 6 Medium 690774213616. Specifications for Reebok Postal Express Chukka Boots - Men's: Manufacturer: Reebok Gender: Male Footwear Type: Boots Toe Type: Soft Color: Black Footwear Upper Fabric/Material:... ... more | FREE shipping go to store |
 | Reebok Postal Express Chukka Boots - Men's Black 5 Medium 690774227453 Reebok Postal Express Chukka Boots - Men's Black 5 Medium 690774227453. Specifications for Reebok Postal Express Chukka Boots - Men's: Manufacturer: Reebok Gender: Male Footwear Type: Boots Toe Type: Soft Color: Black Footwear Upper Fabric/Material:... ... more | FREE shipping go to store |
 | Reebok Postal Express Chukka Boots - Men's Medium Black 16 690774475144 Reebok Postal Express Chukka Boots - Men's Medium Black 16 690774475144. Specifications for Reebok Postal Express Chukka Boots - Men's: Manufacturer: Reebok Gender: Male Footwear Type: Boots Toe Type: Soft Color: Black Footwear Upper Fabric/Material:... ... more | FREE shipping go to store |
 | 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 |
 | Blair Men's Totes® Insulated Side-Zip Boots - Black - 11 - 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 - 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 |
 | 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 |
 | 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 |
 | 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 |
 | DEMO Lowa Renegade Evo Ice GTX Winter Shoes - Men's Black 11 US Medium 4109500999-BLACK-11 US DEMO Lowa Renegade Evo Ice GTX Winter Shoes - Men's Black 11 US Medium 4109500999-BLACK-11 US. This boot is designed to keep feet warm comfortable and protected on snowy outings with a taller shaft for confident striding through snow drifts. It... ... more
DEMO Lowa Renegade Evo Ice GTX Winter Shoes - Men's Black 11 US Medium 4109500999-BLACK-11 US DEMO Lowa Renegade Evo Ice GTX Winter Shoes - Men's Black 11 US Medium 4109500999-BLACK-11 US. This boot is designed to keep feet warm comfortable and protected on snowy outings with a taller shaft for confident striding through snow drifts. It... | FREE shipping go to store |
 | Lowa Renegade Evo Ice GTX Winter Shoes - Men's Black 9 US Medium 4109500999-BLACK-9 US Lowa Renegade Evo Ice GTX Winter Shoes - Men's Black 9 US Medium 4109500999-BLACK-9 US. This boot is designed to keep feet warm comfortable and protected on snowy outings with a taller shaft for confident striding through snow drifts. It features a... ... more
Lowa Renegade Evo Ice GTX Winter Shoes - Men's Black 9 US Medium 4109500999-BLACK-9 US Lowa Renegade Evo Ice GTX Winter Shoes - Men's Black 9 US Medium 4109500999-BLACK-9 US. This boot is designed to keep feet warm comfortable and protected on snowy outings with a taller shaft for confident striding through snow drifts. It features a... | FREE shipping go to store |
 | Lowa Renegade Evo Ice GTX Winter Shoes - Men's Black 11.5 US Medium 4109500999-BLACK-11.5 US Lowa Renegade Evo Ice GTX Winter Shoes - Men's Black 11.5 US Medium 4109500999-BLACK-11.5 US. This boot is designed to keep feet warm comfortable and protected on snowy outings with a taller shaft for confident striding through snow drifts. It features... ... more
Lowa Renegade Evo Ice GTX Winter Shoes - Men's Black 11.5 US Medium 4109500999-BLACK-11.5 US Lowa Renegade Evo Ice GTX Winter Shoes - Men's Black 11.5 US Medium 4109500999-BLACK-11.5 US. This boot is designed to keep feet warm comfortable and protected on snowy outings with a taller shaft for confident striding through snow drifts. It features... | 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 |
 | Reebok Postal Express Chukka Boots - Men's Black 4 Medium 690774227439 Reebok Postal Express Chukka Boots - Men's Black 4 Medium 690774227439. Specifications for Reebok Postal Express Chukka Boots - Men's: Manufacturer: Reebok Gender: Male Footwear Type: Boots Toe Type: Soft Color: Black Footwear Upper Fabric/Material:... ... more | FREE shipping go to store |
 | Reebok Postal Express Chukka Boots - Men's Black 4.5 Medium 690774227446 Reebok Postal Express Chukka Boots - Men's Black 4.5 Medium 690774227446. Specifications for Reebok Postal Express Chukka Boots - Men's: Manufacturer: Reebok Gender: Male Footwear Type: Boots Toe Type: Soft Color: Black Footwear Upper Fabric/Material:... ... more | FREE shipping go to store |
 | Reebok Postal Express Chukka Boots - Men's Black 5.5 Medium 690774227460 Reebok Postal Express Chukka Boots - Men's Black 5.5 Medium 690774227460. Specifications for Reebok Postal Express Chukka Boots - Men's: Manufacturer: Reebok Gender: Male Footwear Type: Boots Toe Type: Soft Color: Black Footwear Upper Fabric/Material:... ... more | FREE shipping go to store |
 | Wolverine Durashocks SR Direct-Attach Lined 6in Work Boot - Men's Black 7.5 US Medium W03123-7.5M Wolverine Durashocks SR Direct-Attach Lined 6in Work Boot - Men's Black 7.5 US Medium W03123-7.5M. The boots Dri-lex-lined pigskin upper wicks for drier feet and seals out water. You'll feel light on your feet and stable with the tough polyurethane... ... more | 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 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 Men's Premium Chukka - 7 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 - 7 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 Men's Premium Chukka - 9 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 - 9 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 |
 | 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 |
 | Timberland Arbor Road Waterproof Chukka - Mens 13 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 13 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 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
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 | 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
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 | $169.95 $152.97 FREE shipping go to store |
 | Timberland Men's Premium Chukka - 9.5 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 - 9.5 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 Atwells Ave WP Chukka - Mens 11.5 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
Timberland Atwells Ave WP Chukka - Mens 11.5 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 | FREE shipping go to store |
 | Timberland Men's Premium Chukka - 8 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 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 9.5 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
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 | 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
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... | 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
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 | 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
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 | $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
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 | $169.95 $152.97 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
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 | FREE shipping go to store |
 | Timberland Arbor Road Waterproof Chukka - Mens 11 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 11 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 Arbor Road Waterproof Chukka - Mens 11.5 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 11.5 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 |
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