No Way! Free Next Day Shipping On Clothing M-F. Order Today, Wear It Tomorrow! Plus Free Returns. Learn More

“chukka and Shoes” we found 589 items!

Choose a
  • Product Type
to sort results

We adjusted your search results to be more relevant. Not what you were looking for? Click here.

Sperry Top-Sider - Striper CVO Chukka Sperry Top-Sider Striper CVO Chukka $70.00 NEW! Sperry Top-Sider - Striper CVO Chukka Sperry Top-Sider Striper CVO Chukka $70.00 NEW! Sperry Top-Sider - Striper CVO Chukka Sperry Top-Sider Striper CVO Chukka $70.00 NEW! The North Face - Base Camp Leather Chukka The North Face Base Camp Leather Chukka $100.00 NEW!
The North Face - Base Camp Leather Chukka The North Face Base Camp Leather Chukka $100.00 NEW! The North Face - Base Camp Leather Chukka The North Face Base Camp Leather Chukka $100.00 NEW! FootMates - Todd 3 (Infant/Toddler) FootMates Todd 3 (Infant/Toddler) $54.95 NEW! FootMates - Tina 2 (Infant/Toddler) FootMates Tina 2 (Infant/Toddler) $54.95 Rated: 5 stars! NEW!
ECCO - Camilla Wedge Ankle Boot ECCO Camilla Wedge Ankle Boot $170.00 NEW! Jambu - Madison Jambu Madison $149.00 NEW! Jambu - Madison Jambu Madison $149.00 NEW! UGG - Lyle UGG Lyle $150.00 Rated: 5 stars! NEW!
Jambu - Madison Jambu Madison $139.00 NEW! Fratelli Rossetti - Chukka Boot Fratelli Rossetti Chukka Boot $482.00 NEW! Marc New York by Andrew Marc - Lexington Marc New York by Andrew Marc Lexington $148.00 NEW! ALDO - Windsor ALDO Windsor $140.00 NEW!
ALDO - Windsor ALDO Windsor $140.00 NEW! SeaVees - 12/67 3 Eye Chukka SeaVees 12/67 3 Eye Chukka $178.00 Rated: 5 stars! NEW! SeaVees - 12/67 3 Eye Chukka SeaVees 12/67 3 Eye Chukka $178.00 Rated: 5 stars! NEW! SeaVees - 12/67 3 Eye Chukka SeaVees 12/67 3 Eye Chukka $178.00 Rated: 5 stars! NEW!
SeaVees - 12/67 3 Eye Chukka SeaVees 12/67 3 Eye Chukka $178.00 Rated: 5 stars! NEW! Patagonia - Japhy Patagonia Japhy $120.00 NEW! Patagonia - Japhy Patagonia Japhy $102.00 NEW! UGG - Lyle UGG Lyle $150.00 Rated: 5 stars! NEW!
Camper - Motel-18911 Camper Motel-18911 $145.00 NEW! Salvatore Ferragamo - Parker Boot Salvatore Ferragamo Parker Boot $560.00 NEW! Salvatore Ferragamo - Parker Boot Salvatore Ferragamo Parker Boot $560.00 NEW! Wolky - Impact II Wolky Impact II $164.00 NEW!
Florsheim - Rockit Chukka Florsheim Rockit Chukka $130.00 NEW! Fratelli Rossetti - ONE Chukka Boot Fratelli Rossetti ONE Chukka Boot $375.00 NEW! Tommy Hilfiger - Barnet2 Tommy Hilfiger Barnet2 $120.00 NEW! El Naturalista - Stella N034 El Naturalista Stella N034 $199.90 NEW!
Fratelli Rossetti - Ultra Light Color Sole Chukka Boot Fratelli Rossetti Ultra Light Color Sole Chukka Boot $440.00 NEW! ASH - Klap ASH Klap $215.00 NEW! SKECHERS - Bruiser SKECHERS Bruiser $69.00 NEW! UGG - Brompton Tweed UGG Brompton Tweed $195.00 NEW!
UGG - Lyle UGG Lyle $150.00 Rated: 5 stars! NEW! UGG - Lyle UGG Lyle $150.00 Rated: 5 stars! NEW! UGG - Brompton UGG Brompton $195.00 NEW! UGG Kids - Orin (Toddler/Little Kid) UGG Kids Orin (Toddler/Little Kid) $65.00 NEW!
UGG - Scottie UGG Scottie $150.00 NEW! Camper - Peu Cami - 36660 Camper Peu Cami - 36660 $185.00 Rated: 5 stars! NEW! Kenneth Cole Reaction Kids - Ticks N Stones (Little Kid/Big Kid) Kenneth Cole Reaction Kids Ticks N Stones (Little Kid/Big Kid) $60.00 NEW! Kenneth Cole Reaction Kids - Ticks N Stones (Little Kid/Big Kid) Kenneth Cole Reaction Kids Ticks N Stones (Little Kid/Big Kid) $60.00 NEW!
Cole Haan - Copley Chukka Boot Cole Haan Copley Chukka Boot $168.00 NEW! Cole Haan - Copley Chukka Boot Cole Haan Copley Chukka Boot $168.00 NEW! Red Wing Heritage - Work Chukka Red Wing Heritage Work Chukka $260.00 Rated: 5 stars! NEW! Kenneth Cole Reaction Kids - Ticks N Stones (Little Kid/Big Kid) Kenneth Cole Reaction Kids Ticks N Stones (Little Kid/Big Kid) $60.00 NEW!
GUESS - Tiverton GUESS Tiverton $120.00 NEW! GUESS - Tiverton GUESS Tiverton $120.00 NEW! Steve Madden - Wiley Steve Madden Wiley $65.00 NEW! Umi Kids - Riker (Toddler/Little Kid) Umi Kids Riker (Toddler/Little Kid) $64.95 NEW!
Umi Kids - Riker II (Little Kid/Big Kid) Umi Kids Riker II (Little Kid/Big Kid) $69.95 NEW! Umi Kids - Riker (Toddler/Little Kid) Umi Kids Riker (Toddler/Little Kid) $64.95 NEW! Umi Kids - Riker II (Little Kid/Big Kid) Umi Kids Riker II (Little Kid/Big Kid) $69.95 NEW! UGG Kids - Orin (Toddler/Little Kid) UGG Kids Orin (Toddler/Little Kid) $65.00 NEW!
UGG - Scottie UGG Scottie $150.00 NEW! Primigi Kids - Ground (Toddler/Little Kid) Primigi Kids Ground (Toddler/Little Kid) $83.00 NEW! Johnston & Murphy - Hartley Chukka Johnston & Murphy Hartley Chukka $195.00 NEW! Steve Madden - Handler Steve Madden Handler $90.00 NEW!
Steve Madden - Handler Steve Madden Handler $90.00 NEW! Steve Madden - Handler Steve Madden Handler $90.00 NEW! Florsheim - Rockit Chukka Florsheim Rockit Chukka $130.00 NEW! Florsheim - Vantage Chukka Florsheim Vantage Chukka $135.00 NEW!
Florsheim - Vantage Chukka Florsheim Vantage Chukka $135.00 NEW! El Naturalista - Stella N034 El Naturalista Stella N034 $199.90 NEW! Kenneth Cole Reaction - Had 2 B U Kenneth Cole Reaction Had 2 B U $138.00 NEW! Florsheim Kids - Flites Chukka Jr. (Toddler/Little Kid/Big Kid) Florsheim Kids Flites Chukka Jr. (Toddler/Little Kid/Big Kid) $69.95 NEW!
Rockport - Eastern Empire Chukka - Plain Toe - 2 Eye Rockport Eastern Empire Chukka - Plain Toe - 2 Eye $170.00 NEW! Rockport - Eastern Empire Chukka - Plain Toe - 2 Eye Rockport Eastern Empire Chukka - Plain Toe - 2 Eye $170.00 NEW! Original Penguin - Birdie Original Penguin Birdie $180.00 NEW! Original Penguin - Birdie Lite Original Penguin Birdie Lite $155.00 NEW!
Original Penguin - Birdie Original Penguin Birdie $180.00 NEW! Primigi Kids - Delfi (Infant/Toddler) Primigi Kids Delfi (Infant/Toddler) $62.80 NEW! Primigi Kids - Erwan-E (Infant/Toddler) Primigi Kids Erwan-E (Infant/Toddler) $70.60 NEW! Primigi Kids - Erwan-E (Infant/Toddler) Primigi Kids Erwan-E (Infant/Toddler) $70.60 NEW!
Primigi Kids - Ground (Toddler) Primigi Kids Ground (Toddler) $76.80 NEW! Primigi Kids - Ground (Little Kid/Big Kid) Primigi Kids Ground (Little Kid/Big Kid) $90.80 NEW! Oliberte - Adibo Oliberte Adibo $150.00 Rated: 5 stars! NEW! Wolverine - Orville Desert Boot Wolverine Orville Desert Boot $155.00 NEW!
Wolverine - Francisco Chukka Wolverine Francisco Chukka $175.00 NEW! Wolverine - Orville Desert Boot Wolverine Orville Desert Boot $155.00 NEW! Wolverine - Francisco Chukka Wolverine Francisco Chukka $175.00 NEW! Wolverine - Orville Desert Boot Wolverine Orville Desert Boot $155.00 NEW!
Camper - Beetle Hi-36530 Camper Beetle Hi-36530 $190.00 Rated: 5 stars! NEW! Steve Madden - Lefir Steve Madden Lefir $75.00 NEW! Oliberte - Adibo Oliberte Adibo $150.00 Rated: 5 stars! NEW! Steve Madden - Gungho Steve Madden Gungho $60.00 NEW!
Steve Madden - Gizmo Steve Madden Gizmo $65.00 NEW! Steve Madden - Gizmo Steve Madden Gizmo $65.00 NEW! Tommy Hilfiger - Kenne Tommy Hilfiger Kenne $90.00 NEW! ECCO - Ethan Retro Boot ECCO Ethan Retro Boot $170.00 NEW!
David Tate - Jersey David Tate Jersey $99.95 NEW! David Tate - Jersey David Tate Jersey $99.95 NEW! Steve Madden - Lefir Steve Madden Lefir $75.00 NEW! Rockport - Eastern Empire Chukka - Plain Toe - 2 Eye Rockport Eastern Empire Chukka - Plain Toe - 2 Eye $170.00 NEW!
Tommy Hilfiger - Kenne Tommy Hilfiger Kenne $90.00 NEW! Polo Ralph Lauren - Barrott Polo Ralph Lauren Barrott $125.00 NEW! Polo Ralph Lauren - Barrott Polo Ralph Lauren Barrott $125.00 NEW! Polo Ralph Lauren - Barrott Polo Ralph Lauren Barrott $125.00 NEW!
Zappos Family Core Value:

10. Be Humble