- Men
- Chukka Boots
$378.99Paul Smith
Cleon Shoes – Chocolate
UK 7 UK 8 UK 9 UK 10 UK 11More details
$480.49Loake
Pimlico Chukka Boot - Dark
7 8 9 10 11More details
$290.49Yogi Footwear
Torres Tumbled & Reverse Leather Crepe Sole Chukka Boot - Olive
UK 7 UK 8 UK 9 UK 10 UK 11More details
$688.49JOSEPH CHEANEY & SONS
Jackie Iii R Chukka Boot Mahogany Country Calf Leather
UK7 UK8 UK9 UK10 UK11More details
$226.99Timberland
Bradstreet Chukka Boot Leather
UK 7 UK 8 UK 9 UK 10 UK 11More details
$157.99Vans
Ua Chukka 49 Dx Dark Brown
41 42 43 44 45More details
$398.99Loake
Mayers Chukka Boot - Tan
7 8 9 10 11More details
$161.99Front
Logan Leather Chukka Boots - Navy
7 8 9 10 11More details
$226.99Timberland
Bradstreet Chukka Boot Nubuck
UK 7 UK 8 UK 9 UK 10 UK 11More details
$271.99Loake
Nubuck Gilbert Chukka Shoes
41 42 43 44 45More details
$226.99Timberland
Wheat Nubuck Bradstreet Chukka Boot
UK 7 UK 8 UK 9 UK 10 UK 11More details
$444.49Sanders & Sanders
Hi Top Suede Polo Snuff Chukka Boot
UK7 UK7.5 UK8 UK9 UK9.5 UK10 UK12More details
$444.49Sanders & Sanders
Indiana Tan Suede Hi Top Chukka Boots
UK7 UK8 UK9 UK10 UK11 UK12More details
$161.99Front
Logan Leather Chukka Boots - Tan
7 8 10 11More details
$105.00The North Face
Black NSE Chukka Boots
7 9 10 11 12 13More details- SALE
$149.99$298.99Padmore & Barnes
Chukka Boot Suede
6 UK 7 UK 8 UK 9 UKMore details 
$239.99Ecco
Men's ST. 1 Hybrid GTX Boot Size 5 Gore-tex
5 6 7 8 12 13More details- SALE
$164.99$175.00Ecco
Men's S. lite Hybrid Chukka Boot Size 5 Gore-tex
5 6 7 8 9 10 12More details 
$172.49John White
Alfie Chukka Boots - Tan
7 8 11More details
$444.49Sanders & Sanders
Hi-top Suede Chukka Boot - Pinner Suede
UK7 UK8 UK9More details- SALE
$129.99$140.00Ecco
Jamestown Men's Ankle Boot Size 7 Leather
7 8 9 10 11 12 13More details - SALE
$139.99$150.00Ecco
Men's Street Lite Chukka Shoe Size 6 Leather
6 7 8 9 10 12 13More details - SALE
$179.99$200.00Ecco
Men's Citytray Chukka Boot Size 5 Leather
5 6 7 8 9 10 11 12 13More details - SALE
$139.99$175.00Ecco
Men's S. lite Hybrid Chukka Boot Size 5 Gore-tex
5 6 7 9 10 11 12More details - $161.49
Vans
Ua Chukka 49 Dx Dark Brown
41 42 43 44 45More details - SALE
$139.99$150.00Ecco
Men's Street Lite Chukka Shoe Size 7 Leather
7 8 9 11 12More details - $449.49
Sanders & Sanders
Hi Top Suede Polo Snuff Chukka Boot
UK7 UK8 UK9 UK9.5 UK10More details 
$1,695.00Kiton
Men's Suede Chukka Boots - Brown - Size 8 - Brown - Size 8
8 9 10 11 12More details- SALE
$280.00$325.00Bruno Magli
Men's Alto Lace Up Chukka Boots
8.5 9 9.5 10 10.5 11 11.5 12 13More details - SALE
$280.00$325.00Bruno Magli
Men's Alto Lace Up Chukka Boots
8.5 9 9.5 10 10.5 11 11.5 12 13More details 
$225.00GreatShirts
Men's Henry Lace Up Chukka Boots
7 8 9 9.5 10 10.5 11 11.5 12 13More details
$225.00GreatShirts
Men's Henry Lace Up Chukka Boots
8 9 9.5 10 10.5 11 11.5 12 13More details- $275.49
Loake
Nubuck Gilbert Chukka Shoes
41 43 44More details 
$1,695.00Kiton
Men's Suede Chukka Boots - Military Green - Size 8 - Military Green - Size 8
8 9 10 11 12More details- SALE
$89.99$109.95Hush Puppies
Men's Detroit Chukka Boots, Size 13 Wide Width, Black Leather
7.5 8 9.5 10 13More details - $449.49
Sanders & Sanders
Hi-top Suede Chukka Boot - Pinner Suede
UK7 UK8 UK9 UK10More details - $449.49
Sanders & Sanders
Indiana Tan Suede Hi Top Chukka Boots
UK9 UK10 UK11 UK12More details 
$414.99Red Wing
3322 Weekender Chukka Boot Copper Rough Tough
UK 8 UK 10More details
$199.95Anthony Veer
Men's Arthur Suede Leather Chukka Boots Men's Shoes
8D 10.5D 11.5D 11D 12D 13DMore details
$145.95Anthony Veer
Men's Bushwick Lace-Up Suede Chukka Boots Men's Shoes
US 7 D US 7.5 D US 8 D US 8.5 D US 9 D US 9.5 D US 10 D US 10.5 D US 11 D US 11.5 D US 12 D US 13 DMore details
$451.49Red Wing
3140 Classic Leather Chukka Boot Oro Iginal Tan
UK 7 UK 8More details
$605.99Barker
Cherry Grain Orkney
UK7/EU41 UK12/EU46More details
$414.99Red Wing
Red Wing Chukka in Copper Rough and Tough Leather 03322D
leather | | 9 leather | | 10More details
$1,550.00Stefano Ricci
Men's Suede Chukka Boots - Dark Brown - Size 8 - Dark Brown - Size 8
8 9 10 11 12More details
$453.00Crockett & Jones
Molton Nubuck Chukka Boots - Mens - Dark Brown
6 UK 7 UK 8 UK 9 UK 10 UK 11 UKMore details
$453.00Crockett & Jones
Chiltern Suede Chukka Boots - Mens - Dark Brown
6 UK 7 UK 8 UK 8.5 UK 9 UK 9.5 UK 10 UK 11 UK 12 UKMore details- SALE
$139.00$164.00Timberland
Newmarket II Chukka boots - Neutrals
8 9 9.5 10 10.5More details 
$620.00Onitsuka Tiger
X Nick Wooster Chukka boots - White
26 26.5 27 27.5 28 29More details- SALE
$83.00$116.00Vans
X Aries OG Chukka Boot LX sneakers - Pink
7 7.5 8 9 9.5 10 11.5 12More details - SALE
$319.00$425.00Scarosso
Suede chukka boots - Neutrals
39 40 40.5 41 41.5 42 43 44 45 46More details - $163.49
Front
Logan Leather Chukka Boots - Tan
7 8 9More details - $174.49
John White
Alfie Chukka Boots - Tan
7 8 11More details - $229.49
Timberland
Bradstreet Chukka Boot Leather
UK 7 UK 9 UK 11More details 
$790.00santoni
Men's Detroit Laceless Chukka Boots
7.5 8 8.5 9 9.5 10 10.5 11 11.5 12More details
$450.00Bruno Magli
Men's Vicolo Lace Up Chukka Boots
8 8.5 9 9.5 10 10.5 11 11.5 12 13More details
$265.00Gordon Rush
Men's Austin Lace Up Chukka Boots
8.5 9 9.5 10 10.5 11 11.5 12 13More details
$265.00Gordon Rush
Men's Austin Lace Up Chukka Boots
8 9 9.5 10 10.5 11 11.5 12 13More details- SALE
$285.00$475.00To Boot
Men's Major Chukka Boots
8 8.5 9 9.5 11 11.5More details 
$745.00Tod's
Men's Polacco Chukka Boots
7.5UK / 8.5US 8.5UK / 9.5US 8UK / 9US 9UK / 10US 10.5UK / 11.5US 10UK / 11US 11UK / 12US 12UK / 13USMore details
$220.00Geox
Men's Brayden 2Fit Abx Waterproof Lace Up Chukka Boots
7US / 40EU 8US / 41EU 10US / 43EU 12.5US / 46EU 12US / 45EUMore details
$780.00santoni
Men's Detroit Laceless Chukka Boots
8 8.5 9 9.5 10 10.5 11 12 13More details
$720.00santoni
Men's Detroit Laceless Chukka Boots
7 8 8.5 9 9.5 11 12More details
$780.00santoni
Men's Detroit Laceless Chukka Boots
8 8.5 9 9.5 10 10.5 11 11.5More details- SALE
$472.50$675.00Tod's
Men's Polacco Chukka Boots
6UK / 7US 7.5UK / 8.5US 7UK / 8US 8.5UK / 9.5US 8UK / 9US 9.5UK / 10.5US 9UK / 10US 10.5UK / 11.5US 10UK / 11US 11UK / 12US 12UK / 13USMore details 
$450.00Bruno Magli
Men's Vicolo Lace Up Chukka Boots
8 9 9.5 10 11 11.5 12More details
$265.00Gordon Rush
Men's Austin Lace Up Chukka Boots
7 7.5 8 8.5 9 9.5 10 10.5 11 11.5 12 13More details- SALE
$90.00$180.00Bloomingdale's
Men's Suede Chukka Boots
7.5 8 8.5 9 9.5 10 11 12 13More details 
$140.00UGG
Men's Neumel Suede Chukka Boots
9 10 11 12 13More details
$140.00UGG
Men's Neumel Suede Chukka Boots
7 8 9 10 11 12 13More details
$140.00UGG
Men's Neumel Suede Chukka Boots
7 8 9 10 11 12 13More details
$115.00Nunn Bush
Men's Ozark Plain Chukka Boots Men's Shoes
7 7.5 8 8.5 8.5XW 8W 9 9.5 9.5XW 9W 10 10.5 10.5W 11 11.5 11W 12 12W 13 13W 15More details
$189.99Thomas & Vine
Men's Banks Moc Toe Chukka Boots Men's Shoes
8.5M 8M 9.5M 9M 10.5M 10M 11.5M 11M 12M 13MMore details
$189.99Thomas & Vine
Men's Banks Moc Toe Chukka Boots Men's Shoes
8.5M 8M 9.5M 9M 10.5M 10M 11.5M 11M 12M 13MMore details- SALE$152.99
$305.99Padmore & Barnes
Chukka Boot Suede
7 UK 8 UK 9 UKMore details - $293.99
Yogi Footwear
Torres Tumbled & Reverse Leather Crepe Sole Chukka Boot - Olive
UK 7 UK 8 UK 9More details - $229.49
Timberland
Bradstreet Chukka Boot Nubuck
UK 8 UK 9 UK 11More details 
$65.00New York And Company
Men's Hurley Chukka Boots Men's Shoes
7.5M 8M 9.5M 9M 10.5M 10M 11M 12MMore details
$220.00ASPORTUGUESAS BY FLY LONDON
Cody Wool Chukka Boot in 004 Black Tweed/Felt at Nordstrom
6 7 8 9 10More details
$269.95Ecco
ST.1 Hybrid Gore-Tex® Boot in Nutmeg Brown at Nordstrom
6 7 8 9 10 11 12 13More details
$269.95Ecco
ST.1 Hybrid Gore-Tex® Boot in Black at Nordstrom
5 6 7 8 9 10 11 12 13 14More details- SALE
$87.50$125.00Timberland
Men's Maple Grove Lace-Up Chukka Boots Men's Shoes
7.5M 8.5M 8M 9.5M 9M 10.5M 10M 11.5M 11M 12M 13MMore details - SALE
$87.50$125.00Timberland
Men's Maple Grove Lace-Up Chukka Boots Men's Shoes
7.5M 8.5M 8M 9.5M 9M 10.5M 10M 11.5M 11M 12M 13MMore details 
$90.00Eastland Shoe
Men's Finn Chukka Boots Men's Shoes
8 8.5 9 9.5 10 10.5 11 11.5 12 13More details
$90.00Eastland Shoe
Men's Finn Chukka Boots Men's Shoes
8 8.5 9 9.5 10 10.5 11 11.5 12 13More details
$120.00Stacy Adams
Men's Tilden Plain Toe Chukka Boots Men's Shoes
7.5M 7M 8.5M 8M 9.5M 9M 10.5M 10M 11.5M 11M 12M 13M 14MMore details
$375.00Bruno Magli
Men's Orlando Chukka Boots Men's Shoes
7M 8.5M 9.5M 9M 10.5M 10M 11M 12MMore details
$109.00The North Face
Men's Nse Chukka Boots Men's Shoes
7.5M 7M 8.5M 8M 9.5M 9M 10.5M 10M 11.5M 11M 12.5M 12M 13M 14MMore details
$159.99Territory
Men's Redwoods Chukka Boots Men's Shoes
8.5M 8M 9.5M 9M 10.5M 10M 11.5M 11M 12M 13MMore details
$159.99Territory
Men's Redwoods Chukka Boots Men's Shoes
8.5M 8M 9.5M 9M 10.5M 10M 11.5M 11M 12M 13MMore details
$169.00Vince Camuto
Men's Stuwert Casual Chukka Boot Men's Shoes
8 8.5 9 9.5 10 10.5 11 11.5 12 13More details
$169.00Vince Camuto
Men's Saveli Casual Chukka Boot Men's Shoes
8 8.5 9 9.5 10 10.5 11 11.5 12 13More details
$125.00Timberland
Davis Square Chukka boots - Brown
8 8.5 9 9.5More details
$109.99Vance Co.
Men's Jimmy Plain Toe Chukka Boots Men's Shoes
8 8.5 9 9.5 10 10.5 11 11.5 12 13More details
$109.99Vance Co.
Men's Barett Knit Chukka Boots Men's Shoes
8 8.5 9 9.5 10 10.5 11 11.5 12 13 14More details
$115.00Nunn Bush
Men's Odell Wingtip Chukka Boots Men's Shoes
8.5 8.5XW 8XW 9W 9XW 10 10.5 10.5W 10XW 11 12XWMore details
$169.00Vince Camuto
Men's Saveli Casual Chukka Boot Men's Shoes
8 9 9.5 10 11 13More details- SALE
$158.90$265.00Gordon Rush
Men's Austin Lace Up Chukka Boots
10 11 12 13More details 
$269.00Karl Lagerfeld
Urano Iv Chukka Lace Boots, Man, , Size: 40
40 41 42 43 44 45 46More details