Men's Chukka Boots – heel boy

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Vagabond Women's 5002 Hedda in Black

Vagabond Women's 5002 Hedda in Black

Vagabond Women's 5002 Hedda in Black

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black leather block heel pump with bow detail on a white background

heel boy Women's Paloma in Black

heel boy Women's Paloma in Black

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Camper Women's Casi Myra K201253-057 in Brown

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FLOOF Gingham Frill Sock in Black and White

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Sam Edelman Women's Magnolia in Java Brown

Sam Edelman Women's Magnolia in Java Brown

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Miz Mooz Women's Vayda in Cognac

Miz Mooz Women's Vayda in Cognac

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Floof Unisex Spooky Season Cap in Black

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Back 70 Women's Cloud UK04 in Loden Olive/Olive

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Back 70 Women's Cloud UK04 in Loden Olive/Olive

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Floof Gingham Frill Sock in Navy
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Camper Women's Louise Sandal K201915-002 In White
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Women
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  Boots
  
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  Heels
  
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  Sneakers
  
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  Winter Boots
  
  All Gendered
  
  Shop All Women's Shoes
- Shop by Occasion
  
  Back to School
  
  Rain
  
  Weddings & Events
  
  Gardening
  
  Hiking Sandals
  
  Office & Workwear
  
  Vacation & Resort
  
  Snow & Winter
  
  Shop All Women's Shoes
- Shop by Trend
  
  Bestsellers
  
  Spring New Arrivals
  
  Currently Loving
  
  Jelly Flats & Sandals
  
  Mesh Footwear
  
  Woven Detail
  
  Sneaker Mules
  
  Sneakerinas
  
  Slogan Hats
  
  Shop All Women's Shoes
- Shop by Brand
  
  Badgley Mischka
  
  Camper
  
  G.H. Bass
  
  Hanky Panky
  
  Miz Mooz
  
  New Balance
  
  Sam Edelman
  
  UGG
  
  Vagabond Shoemakers
  
  Shop All Brands
- Accessories
  
  Jackets & Coats
  
  All Bags
  
  Baseball Hats
  
  Clutches
  
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  Umbrellas
  
  Mittens & Gloves
  
  Scarves & Hats
  
  Travel Accessories
  
  Shop All Accessories
- Shop by Feature
  
  Arch Support
  
  Extended Width
  
  Lightweight
  
  Removable Insole
  
  Podiatrist Recommended
  
  Recycled Materials
  
  Slip Resistant
  
  Waterproof
  
  Vegan
  
  Shop All Women's Shoes
- Shop by Weather
  
  Rain Ready
  
  Snow Ready
  
  Ice Gripper Outsole
  
  Weatherproof Leather
  
  Weatherproof Suede
- Deals
  
  Under $100
  
  Shop All Sale
Men
- Shop by Type
  
  Sneakers
  
  Boots
  
  Loafers
  
  Dress Shoes
  
  Sandals
  
  Chukka Boots
  
  Oxford Shoes
  
  Slippers
  
  All Gendered
  
  Shop All Men's Shoes
- Shop by Occasion
  
  Events & Weddings
  
  Work Boots
  
  Running Shoes
  
  Snow & Winter
  
  Hiking
  
  Gift Guide
  
  House Shoes
  
  Father's Day Shop
  
  Shop All Men's Shoes
- Shop by Trend
  
  Bestsellers
  
  New In
  
  Combat Boots
  
  Shop All Men's Shoes
- Shop by Brand
  
  Cole Haan
  
  G.H. Bass
  
  Johnston & Murphy
  
  New Balance
  
  On Running
  
  Palladium
  
  Pajar
  
  Xtratuf
  
  Shop All Brands
- Accessories
  
  Belts
  
  Umbrellas
  
  Travel Bags & Accessories
  
  Mittens & Gloves
  
  Socks & Boxers
  
  Jackets & Coats
  
  Hats & Scarves
  
  Groom Care
  
  Shop All Accessories
- Shop by Feature
  
  Cushioned Shoes
  
  Breathable Upper
  
  Extended Width
  
  Removable Insole
  
  Lightweight Shoes
  
  Slip Resistant
  
  Steel Toe
  
  Waterproof
  
  Vegan
  
  Shop All Men's Shoes
- Shop by Weather
  
  Rain Ready
  
  Snow Ready
  
  Weatherproof Leather
  
  Weatherproof Suede
  
  Ice Gripper Outsole
- Deals
  
  Under $100
  
  Shop All Men's Sale
Kids'
- Shop by Type
  
  New Arrivals
  Boots
  Flats
  Rain Boots
  Sneakers
  Sandals
  Winter Boots
  Shop All
- Shop by Brand
  
  Badgley Mishcka Kids
  Cougar Kids
  Camper Kids
  Joybees Kids
  Merrell Kids'
  Saucony Kids'
Accessories
- Bags
- Mittens & Gloves
- Hats & Scarves
- Jackets & Coats
- Socks & Intimates
- Hair Accessories
- Sunglasses
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- Shop All Accessories
Shop By Brand
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Home Collection Men's Chukka Boots

Styles & sizes will vary in-stores

Collection: Men's Chukka Boots

Weather-ready and effortlessly stylish—find men’s boots for every occasion

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Camper Men's Norman in Black

Camper Men's Norman in Black

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Camper Men's Norman in Black

Regular price $235.00 CAD

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Camper Men's Dean K300493-001 in Black

Camper Men's Dean K300493-001 in Black

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Camper Men's Dean K300493-001 in Black

Regular price $265.00 CAD

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Rockport Men's Caspe In British W

Rockport Men's Caspe In British W

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Rockport Men's Caspe In British W

Regular price $250.00 CAD

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Rockport Men's Caspe In Black/Black W

Rockport Men's Caspe In Black/Black W

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Rockport Men's Caspe In Black/Black W

Regular price $250.00 CAD

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Astorflex Men's Bootflex Boot in Gunmetal

Astorflex Men's Bootflex Boot in Gunmetal

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Astorflex Men's Bootflex Boot in Gunmetal

Regular price $389.00 CAD

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Sorel Men's Madson II Chukka WP in Tobacco

Sorel Men's Madson II Chukka WP in Tobacco

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Sorel Men's Madson II Chukka WP in Tobacco

Regular price $210.00 CAD

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Sorel Men's Madson II Chukka WP in Major

Sorel Men's Madson II Chukka WP in Major

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Sorel Men's Madson II Chukka WP in Major

Regular price $210.00 CAD

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Vince. Men's Jerome in Birchwood

Vince. Men's Jerome in Birchwood

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Vince. Men's Jerome in Birchwood

Regular price $450.00 CAD

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Vince. Men's Jerome in Cocoa Brown

Vince. Men's Jerome in Cocoa Brown

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Vince. Men's Jerome in Cocoa Brown

Regular price $450.00 CAD

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Men's Chukka Boots

Chukka boots strike the balance between rugged and refined, giving you comfort, versatility, and a look that works anywhere.

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