Chukka Boots

Showing 1–20 of 431 results

BrandAllJohnston & MurphyRedSteve Madden
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CategoryAllBootsShoes

Cole Haan Men’s Grand Tour Chukka Boots Men’s Shoes
A lightweight, sneaker-like design and fashion-forward lines on the Grand Tour Chukka Boots by Cole Haan offer to elevate your casual look with fresh style and a supremely cushioned feel ...
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$180.00Buy

Cole Haan Men’s ZERØGRAND Stitchlite Wool Chukka Boots Men’s Shoes
Run, do not walk to the head of the pack in both style and comfort with Cole Haan's revolutionary sneaker-meets-dress boot ZERØGRAND chukka boots. Grand.ØS technology delivers a cushioned feel ...
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$200.00Buy

Deer Stags Men’s Walkmaster Classic Comfort Chukka Boot Men’s Shoes
You don't have to compromise comfort to look great. The Deer Stags Walkmaster series shoes will be your secret weapon, letting you feel and look like a million bucks ...
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$90.00Buy

Deer Stags Men’s James 2 Dress Comfort Classic Chukka Boot Men’s Shoes
A classic chukka redefined, the Deer Stags James 2 is sure to be your favorite pair of boots this season. The contrasting blonde sole makes just the right amount of ...
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$70.00Buy

Deer Stags Men’s Irvine Lightweight Dress Comfort Casual Fashion Chukka Boot Men’s Shoes
Style and comfort. Who knew they could coexist The Deer Stags Irvine will elevate your outfit without hurting your feet. A styling mixing of materials meets a classic cap toe ...
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$80.00Buy

Deer Stags Men’s Jayden Lightweight Memory Foam Dress Comfort Classic Cap Toe Chukka Boot Men’s Shoes
A classic chukka redefined, the Deer Stags Jayden is sure to be your favorite pair of boots this season. The contrasting blonde sole makes just the right amount of fashion ...
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$70.00Buy

Deer Stags Men’s Freeport Dress Casual Comfort Chukka Boot Men’s Shoes
A new classic. The Freeport will be your go-to for showing the world you know how to dress well. The classic chukka style gets an update with contrast stitching and ...
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$80.00Buy

Frye Men’s Murray Chukka Boots Men’s Shoes
The Murray chukkas from Frye elevate your cool-casual look with their ankle-high silhouette and smooth nubuck styling ...
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$298.00Buy

Frye Men’s Explorer Leather Chukka Boots Men’s Shoes
Evocatively named 'Explorer', these Chukka boots from Frye are perfect for wearing on adventurous days that require substantial footwear. This pair has been constructed with protective yet extremely lightweight leather ...
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$298.00Buy

Polo Ralph Lauren Men’s Talan Chukka Boots Men’s Shoes
The Talan pairs the classic chukka silhouette with a durable performance rubber outsole. A refined suede upper adds a dapper aesthetic to Polo Ralph Lauren's casual boot ...
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$125.00Buy