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| Best Seller  | Kezar Waterproof Suede Chukka Boots Men's Sorel Kezar Waterproof Suede Chukka Boots - Brown - Casual boots Sorel "Kezar" waterproof suede boots. Round moccasin toe. Laceup vamp. Logo at tongue. Wool/polyester lining. EVA footbed. Sawtooth rubber sole. Imported. more | FREE shipping go to store |
 | Chandler Weatherproof Leather Chukka Boots Men's Allen Edmonds Chandler Weatherproof Leather Chukka Boots - Brown - Casual boots Allen Edmonds "Chandler" chukka boots in waterproof leather 360o bench welt construction for durability and stability 0.75 in / 20 mm stacked heel Round toe Lace-up... more | FREE shipping go to store |
| Best Seller  | Men's Nunn Bush Otto Plain Toe Chukka Boot - Brown - Casual boots The classic design of the Otto plain toe chukka boot from Nunn Bush brings versatile stylings to your wardrobe. The Defender Repellant upper offers a waterproof finish, while the Memory... more | FREE shipping go to store |
 | Columbia Techlite Comfort Leather Men's Waterproof Chukka Boots In A Size 10.5. Color Is Mountain Red. Do Have Some Marks But Not Bad. Nice Pair Of Boots. Thanks For Shopping With Us! more | go to store |
 | Columbia Mens 10 Irvington Ii Chukka Leather Waterproof Boots Winter Brown Lace Rubber Sole Lace Up Ankle Boots Solid Non-Marking Rubber Outsole Techlite Lightweight Cushioned Midsole Waterproof Leather Boot With An Ultra-Cushioned Midsole Is Made For... more | go to store |
 | Reposhing This Item I Purchased From @Vanlifepickers. Loved It, But Ready To Rotate For Something New. Questions? Leave A Comment Below! more | go to store |
 | Timberland Arbor Road Waterproof Chukka - Mens 10.5 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 $101.97 FREE shipping go to store |
 | Timberland Redwood Falls Waterproof Chukka - Mens 10.5 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 |
 | Timberland Redwood Falls Waterproof Chukka - Mens 11 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 |
 | ® Neumel Weather Hybrid Suede/waterproof Classic Boots - Black - Ugg Boots Men's Ugg ® Neumel Weather Hybrid Suede/waterproof Classic Boots - Black - Casual boots Our iconic heritage chukka gets a weatherized upgrade. A timeless boot made of rich, waterproof suede, it's lined in our UGG®plush upcycled wool blend and finished... more | $180.00 $126.00 go to store |
 | Neumel Weather Ii Boot - Black - Ugg Boots Men's Ugg Neumel Weather Ii Boot - Black - Casual boots Your favorite chukka boot now incorporates waterproof features to help keep you looking better for longer. Crafted with seam-sealed construction and waterproof leather lined in our ultra-soft... more | $160.00 $112.00 go to store |
 | Sorel Men's Madson Ii Chukka Boot - Brown Features a waterproof leather and suede upper with waterproof membrane construction. Removable molded EVA footbed, synthetic topcover. Full length molded EVA midsole. Molded rubber outsole. Measurements based on size 9 - Heel Height: 1 in. Platform... more | $216.00 $130.00 go to store |
 | Sorel Men's Madson Ii Chukka Boot - Green Features a waterproof leather and suede upper with waterproof membrane construction. Removable molded EVA footbed, synthetic topcover. Full length molded EVA midsole. Molded rubber outsole. Measurements based on size 9 - Heel Height: 1 in. Platform... more | $216.00 $130.00 go to store |
 | Sorel Men's Madson Ii Chukka Boot - Brown Features a waterproof leather and suede upper with waterproof membrane construction. Removable molded EVA footbed, synthetic topcover. Full length molded EVA midsole. Molded rubber outsole. Measurements based on size 9 - Heel Height: 1 in. Platform... more | $216.00 $130.00 go to store |
 | Men's Chaco Paonia Desert Chukka Boot - Brown - Desert boots Elegant and casual in equal parts, the Paonia Desert chukka boot from Chaco makes a versatile addition to your shoe collection. This lace-up boot flaunts a waterproof, Gold-rated waxy suede... more | FREE shipping go to store |
 | Men's Nunn Bush Otto Plain Toe Chukka Boot - Blue - Casual boots The classic design of the Otto plain toe chukka boot from Nunn Bush brings versatile stylings to your wardrobe. The Defender Repellant upper offers a waterproof finish, while the Memory... more | FREE shipping go to store |
 | Men's Nunn Bush Otto Plain Toe Chukka Boot - Black - Casual boots The classic design of the Otto plain toe chukka boot from Nunn Bush brings versatile stylings to your wardrobe. The Defender Repellant upper offers a waterproof finish, while the Memory... more | FREE shipping go to store |
 | Men's Nunn Bush Otto Plain Toe Chukka Boot - Black - Casual boots The classic design of the Otto plain toe chukka boot from Nunn Bush brings versatile stylings to your wardrobe. The Defender Repellant upper offers a waterproof finish, while the Memory... more | FREE shipping go to store |
 | Chandler Weatherproof Leather Chukka Boots Men's Allen Edmonds Chandler Weatherproof Leather Chukka Boots - Brown - Casual boots Allen Edmonds "Chandler" chukka boots in waterproof leather 360º bench welt construction for durability and stability 0.50 in / 15 mm stacked heel Round toe Laceup... more | FREE shipping go to store |
 | Men's Chaco Paonia Desert Chukka Boot - Green - Desert boots Elegant and casual in equal parts, the Paonia Desert chukka boot from Chaco makes a versatile addition to your shoe collection. This lace-up boot flaunts a waterproof, Gold-rated waxy suede... more | FREE shipping go to store |
 | Columbia Men’s Chinook Chukka Waterproof Boot - Maroon/Red - Size 11 Sb4 more | 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 Redwood Falls Waterproof Chukka - Mens 11.5 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 |
 | Timberland Arbor Road Waterproof Chukka - Mens 11 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 $101.97 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 | $169.95 $118.97 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 |
 | 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 $101.97 FREE shipping go to store |
 | Nunn Bush Denali Plain Toe Waterproof Chukka - Mens 8 Black Boot W *Seam-sealed waterproof leather upper *Breathable Suedetec lining engineered for moisture management *Fully-cushioned Comfort Gel Memory Foam footbed with Softgel heel pod *Lightweight, durable EVA and rubber outsole more | FREE shipping 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 | $169.95 $118.97 FREE shipping go to store |
 | Timberland Arbor Road Waterproof Chukka - Mens 7 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 $101.97 FREE shipping go to store |
 | Nunn Bush Denali Plain Toe Waterproof Chukka - Mens 10.5 Black Boot W *Seam-sealed waterproof leather upper *Breathable Suedetec lining engineered for moisture management *Fully-cushioned Comfort Gel Memory Foam footbed with Softgel heel pod *Lightweight, durable EVA and rubber outsole more | FREE shipping go to store |
 | Timberland Arbor Road Waterproof Chukka - Mens 8 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 $101.97 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 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 $118.97 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 $118.97 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 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 | $169.95 $118.97 FREE shipping go to store |
 | Timberland Redwood Falls Waterproof Chukka - Mens 9 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 10 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 $101.97 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 | $169.95 $101.97 FREE shipping go to store |
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