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Through biting cold, slush, sleet and ice, a guy has to have a reliable pair of boots to get through winter. Vibrant suede chukkas add a pop to your wardrobe while wingtip boots keep things classy. From total utility to flashy style, this collection of boots and chukkas will have your feet winterized and ready for the day.
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The Generic Man Men’s Chuckman Suede Chukka (Green/Brown)$310$119.00 -
The Generic Man Men’s Chuckman Suede Chukka (Indigo/Brown)$310$119.00 -
The Generic Man Men’s Chuckman Suede Chukka (Red City/Brown)$310$119.00 -
The Generic Man Men’s Florentine Suede Chukka (Black)$355$129.00 -
The Generic Man Men’s Florentine Suede Chukka (Indigo)$355$129.00 -
Rogue Men’s Keith Chukka (Ghurka)$195$89.00 -
Rogue Men’s Rycroft Chukka Boot (Red)$350$99.00 -
Rogue Men’s Huntington Chukka (Black)$175$70.00 -
Rogue Men’s Huntington Chukka (Taupe)$175$70.00 -
Gordon Rush Collection Men’s Taylor Chukka Boot (Brown Suede)$420$159.00 -
Tod’s Men’s Chukka (Blue)$467$349.00 -
Tod’s Men’s Moc-Toe Chukka (Taupe)$457$339.00 -
Tod’s Men’s Chukka (Beige)$467$349.00 -
Andrew Marc Men’s Dorchester Chukka (Med Blue)$178$89.00 -
Andrew Marc Men’s Dorchester Chukka (Oxblood)$178$89.00 -
Andrew Marc Men’s Dorchester Chukka (Veridian)$178$89.00 -
Florsheim Men’s Tienomite Mid Boat Shoe (Brown)$145$69.00 -
Florsheim Men’s Tienomite Mid Boat Shoe (Navy)$145$69.00 -
The Generic Man Men’s Chuckman Leather Chukka (Black)$310$119.00 -
The Generic Man Men’s Bouncer Leather Lace-Up (Black)$360$162.00 -
The Generic Man Men’s Bouncer Leather Lace-Up (Grey)$360$162.00 -
Tretorn Men’s Otto Mid Canvas Sneaker (Safari Beige)$75$26.00 -
Swear London Men’s Monkstrap Chukka (Black)$270$109.00 -
Swear London Men’s Monkstrap Chukka (Brown)$270$109.00 -
Swear London Men’s Chukka (Black)$210$89.00 -
Swear London Men’s Chukka (Sand)$210$89.00 -
Swear London Men’s Chukka (Black)$260$109.00 -
Swear London Men’s Chukka (Grey)$260$109.00 -
Swear London Men’s Chukka (Black)$260$109.00 -
Dino Bigioni Men’s Chukka Boot (Brown Lama)$475$199.00 -
Tod’s Men’s Chukka (Dark Beige)$632$469.00 -
Tod’s Men’s Ankle Boot (Brown)$478$359.00 -
Tod’s Men’s Lace-Up Boot (Taupe)$522$389.00 -
Bruno Magli Men’s Malcolm Chukka (Black)$450$189.00 -
Andrew Marc Men’s Hudson Chukka (Castor/Antilope)$118$54.00 -
Andrew Marc Men’s Hudson Chukka (Coal/Black)$118$54.00 -
Andrew Marc Men’s Hudson Chukka (Olive/Gum)$118$54.00 -
John Varvatos Men’s NYC Vintage Chukka (Mineral Black)$298$129.00 -
John Varvatos Men’s NYC Vintage Chukka (Whiskey)$298$129.00 -
Rockport Men’s Toloni Boot (Brown)$136$69.00 -
Oliberte Men’s Zimbo Chukka Boot (Antique Brown)$170$89.00 -
Oliberte Men’s Zimbo Chukka Boot (Black/Grey)$170$89.00 -
Oliberte Men’s Zimbo Chukka Boot (Black/Grey Pullup)$170$89.00 -
Oliberte Men’s Zimbo Chukka Boot (Camel)$170$89.00 -
Oliberte Men’s Zimbo Chukka Boot (Dark Grey)$170$89.00 -
Ben Sherman Men’s Aberdeen Leather Chukka (Black)$140$52.00 -
Ben Sherman Men’s Abe Chukka Boot (Blue)$155$64.00 -
Eastland Men’s Daily Double Boot (Black)$110$49.00 -
Eastland Men’s Uptown Boot (Dark Brown)$135$79.00 -
Eastland Men’s Stonington 1955 Camp Moc Boot (Black)$215$79.00 -
Wolverine No. 1883 Men’s Seger Engineer Boot (Brown)$200$79.00 -
Oliberté Men’s Kuko Boots (Olive/Tan)$174$59.00 -
Andrew Marc Men’s Roxbury Boot (Asphalt/Deep Natural/Black)$268$109.00 -
Andrew Marc Men’s Roxbury Boot (Wood Black/Deep Natural/Black)$268$109.00 -
Dr. Martens Unisex Isaac Boot (Brown Oil Tan)$230$79.00 -
Dr. Martens Unisex Wallis Boot (Black Berkshire)$200$69.00 -
Eastland Men’s Belgrade 1955 Kiltie Boot (Black)$225$79.00 -
Eastland Men’s Belgrade 1955 Kiltie Boot (British Tan)$225$79.00 -
Eastland Men’s Belgrade 1955 Kiltie Boot (Chestnut)$225$79.00 -
Rockport Men’s Castleton Boot (Black)$160$79.00 -
Rockport Men’s Castleton Boot (Tan)$160$79.00 -
Rockport Men’s Union Street Wingtip Boot (Black)$200$79.00 -
Generic Surplus Men’s Mojave Boot (Military Green/Monk’s Robe)$125$24.00 -
Generic Surplus Men’s Mojave Boot (Mood Indigo/Earth)$125$24.00 -
Calvin Klein Men’s Gale Boot (Black/Charcoal)$190$79.00 -
Florsheim By Duckie Brown Men’s Military Boot (Black Patent)$475$199.00 -
Florsheim By Duckie Brown Men’s Military Boot (Cognac)$475$199.00 -
Florsheim By Duckie Brown Men’s Military Boot (Olive)$475$199.00 -
The Generic Man Men’s Wingman Boot (Black/Blue)$395$139.00 -
The Generic Man Men’s Wingman Boot (Grey)$395$139.00 -
John Varvatos Men’s Driggs Hidden Lace Boot (Brownstone)$298$129.00 -
John Varvatos Men’s Driggs Hidden Lace Boot (Coal)$298$129.00 -
Antonio Maurizi Men’s Burnished Medallion Wingtip Boot (Black)$695$249.00 -
Antonio Maurizi Men’s Burnished Medallion Wingtip Boot (T.moro)$695$249.00 -
Generic Surplus Men’s Ledger Crepe Boot (Black)$150$59.00 -
Generic Surplus Men’s Ledger Crepe Boot (Monks Robe)$150$59.00 -
Dr. Martens Men’s Beckett Lace Up Boot (Stone)$290$79.00 -
Dr. Martens Men’s Beckett Lace Up Boot (Taupe)$290$159.00 -
Dr. Martens Unisex Beckett Beckett (Black)$200$79.00
