- Men
- Chukka Boots
- Wool
Bloomingdale's$140.00UGGMen's Neumel Suede Chukka Boots
9 10 11 12 13More details
Bloomingdale's$140.00UGGMen's Neumel Suede Chukka Boots
7 8 9 10 11 12 13More details
Bloomingdale's$140.00UGGMen's Neumel Suede Chukka Boots
7 8 9 10 11 12 13More details
Urban Outfitters$130.00UGGNeumel Chukka Boot
M 8More details
Selfridges & Co$152.00UGGMens Classic Ultra Mini Shearling-lined Suede Ankle Boots 8
8 10 11 12More details
Selfridges & Co$152.00UGGMens Classic Ultra Mini Sheepskin Boots 8
8 9 10 11 12More details
Saks Fifth Avenue$1,550.00Stefano RicciMen's Suede Chukka Boots - Black - Size 6 - Black - Size 6
6 7 8 9 10More details
Trouva$265.99LoakeNubuck Gilbert Chukka Shoes
41 42 43 44 45More details
Saks Fifth Avenue$1,300.00Stefano RicciMen's Calfskin Leather Chukka Boots - Black - Size 5 - Black - Size 5
5 6 8 9 10More details
Saks Fifth Avenue$1,550.00Stefano RicciMen's Suede Chukka Boots - Dark Brown - Size 6 - Dark Brown - Size 6
6 7 8 9 10More details
Bloomingdale's$225.00GreatShirtsMen's Henry Lace Up Chukka Boots
7 8 9 9.5 10 10.5 11 11.5 12 13More details
Bloomingdale's$225.00GreatShirtsMen's Henry Lace Up Chukka Boots
7 8 9 9.5 10 10.5 11 11.5 12 13More details
Trouva$279.99Yogi FootwearWinstone Crepe Leather - Handcrafted In Portugal
40 41 42 43More details
Saks Fifth Avenue$1,700.00Stefano RicciMen's Suede Chukka Boots - Dark Red - Size 6 - Dark Red - Size 6
6 7.5 10More details
Saks Fifth Avenue$200.00ClarksMen's Wallabee Chukka Boots - Navy Shashiko - Size 8 - Navy Shashiko - Size 8
8 9 10 11 12More details
Saks Fifth Avenue$265.00Gordon RushMen's Austin Chukka Boots - Espresso - Size 7 - Espresso - Size 7
7 7.5 8 9 9.5 10 10.5 11.5 13More details
Saks Fifth Avenue$139.95UGGMen's Neumel Suede Chukka Boots - Chestnut - Size 7 - Chestnut - Size 7
7 8 10 11 12 13More details
Saks Fifth Avenue$139.95UGGMen's Neumel Suede Chukka Boots - Black - Size 8 - Black - Size 8
8 9 10 11 12 13More details
Trouva$283.49Yogi FootwearTorres Tumbled & Reverse Leather Crepe Sole Chukka Boot - Olive
UK 7 UK 8 UK 9 UK 10 UK 11More details
Trouva$155.49VansUa Chukka 49 Dx Dark Brown
41 42 43 44 45More details
Trouva$469.99LoakePimlico Chukka Boot - Dark
7 8 9 10 11More details
Trouva$673.49JOSEPH CHEANEY & SONSJackie Iii R Chukka Boot Mahogany Country Calf Leather
UK7 UK8 UK9 UK10 UK11More details
Trouva$434.49Sanders & SandersIndiana Tan Suede Hi Top Chukka Boots
UK7 UK8 UK9 UK10 UK11 UK12More details
Trouva$221.99TimberlandBradstreet Chukka Boot Nubuck
UK 7 UK 8 UK 9 UK 10 UK 11More details
Trouva$221.99TimberlandBradstreet Chukka Boot Leather
UK 7 UK 8 UK 9 UK 10 UK 11More details
Trouva$221.99TimberlandWheat Nubuck Bradstreet Chukka Boot
UK 7 UK 8 UK 9 UK 10 UK 11More details
Trouva$434.49Sanders & SandersHi Top Suede Polo Snuff Chukka Boot
UK7 UK7.5 UK8 UK8.5 UK9 UK9.5 UK10 UK12More details
SSENSE$105.00The North FaceBlack NSE Chukka Boots
7 8 9 10 12 13More details
Trouva$249.49Yogi FootwearTorres Nubuck Chukka Boot On Crepe — Stone
40 41 42More details
Trouva$249.49Yogi FootwearHitch Rev Tumb Boot On Crepe Outsole — Chestnut
40 41 42More details
FARFETCH$620.00Onitsuka TigerX Nick Wooster Chukka boots - White
26 26.5 27 27.5 28 29More details- SALE
FARFETCH$81.00$116.00VansX Aries OG Chukka Boot LX sneakers - Pink
5.5 7 7.5 8 9 9.5 10 11.5 12More details 
FARFETCH$425.00ScarossoSuede chukka boots - Neutrals
39 40 40.5 41 41.5 42 43 43.5 44 45 46 47More details
Saks Fifth Avenue$95.00UGGLittle Kid's & Kid's Neumel II Chukka Boots - White - Size 6 (Child) - White - Size 6 (Child)
6 (Child) 7 (Child) 8 (Toddler) 12 (Child)More details- SALE
Saks Fifth Avenue$296.25$395.00To BootMen's Dickens Leather Chukka Boots - Softy Blue - Size 8 - Softy Blue - Size 8
8 9 9.5 11More details 
Trouva$158.49FrontLogan Leather Chukka Boots - Navy
7 9 10 11More details
Trouva$434.49Sanders & SandersHi-top Suede Chukka Boot - Pinner Suede
UK7 UK8 UK9 UK10More details
Trouva$158.49FrontLogan Leather Chukka Boots - Tan
7 9 10 11More details
Trouva$389.99LoakeMayers Chukka Boot - Tan
7 9 10 11More details- SALE
Trouva$147.99$295.49Padmore & BarnesChukka Boot Suede
6 UK 7 UK 8 UK 9 UKMore details 
Trouva$310.99YMCYogi Footwear Archer Leather Handcrafted In Portugal
37 39 41 43More details
Trouva$295.49Yogi FootwearLucas Tumbled Leather Moccasin Vibram Boot Handcrafted In Portugal
40 41 42More details
Trouva$279.99Yogi FootwearWinstone Crepe Leather Handcrafted In Portugal
36 38 40 41More details
Nordstrom$249.95EccoST.1 Hybrid Gore-Tex® Boot in Nutmeg Brown at Nordstrom
7 9 10 13 14More details
FARFETCH$125.00TimberlandDavis Square Chukka boots - Brown
8 8.5 9 9.5More details
Saks Fifth Avenue$1,300.00Stefano RicciMen's Calfskin Suede Chukka Boots - Blue - Size 8.5 - Blue - Size 8.5
8.5 10.5More details- SALE
Saks Fifth Avenue$104.96$139.95UGGMen's Neumel Suede Chukka Boots - Samba Red - Size 8 - Samba Red - Size 8
8 9 14More details 
Trouva$168.49John WhiteAlfie Chukka Boots - Tan
7 8 11More details
Trouva$405.99Red Wing3322 Weekender Chukka Boot Copper Rough Tough
UK 8 UK 9 UK 10More details
Bloomingdale's$450.00Bruno MagliMen's Vicolo Lace Up Chukka Boots
8 9.5 10 10.5 11 11.5More details
Bloomingdale's$265.00Gordon RushMen's Austin Lace Up Chukka Boots
9 9.5 10.5 11.5 12 13More details
Bloomingdale's$265.00Gordon RushMen's Austin Lace Up Chukka Boots
8 9 9.5 10 10.5 11.5 13More details- SALE
Bloomingdale's$243.75$325.00Kenneth ColeMen's Albert Lace Up Chukka Boots
7 7.5 8 9 10 10.5 11 12 13More details - SALE
Bloomingdale's$224.00$320.00Cole HaanMen's 2.ZERGRAND Lace Up Chukka Boots
8 M 8.5 9 M 10 M 11 M 11.5 12More details - SALE
Bloomingdale's$243.75$325.00Kenneth ColeMen's Albert Lace Up Chukka Boots
8 8.5 9 9.5 10 10.5 11 11.5 12 13More details - SALE
Bloomingdale's$332.50$475.00To BootMen's Major Chukka Boots
8 8.5 9 9.5 10.5 11 11.5 12 13More details 
Bloomingdale's$675.00Tod'sMen's Polacco Chukka Boots
7.5UK / 8.5US 8.5UK / 9.5US 8UK / 9US 9UK / 10US 10.5UK / 11.5US 10UK / 11US 11UK / 12USMore details
Bloomingdale's$220.00GeoxMen's Brayden 2Fit Abx Waterproof Lace Up Chukka Boots
7US / 40EU 8US / 41EU 10US / 43EU 12US / 45EU 13US / 46EUMore details
Bloomingdale's$220.00NisoloMen's Everyday Chukka Boots
8.5 9 9.5 10 10.5 11 11.5More details
Bloomingdale's$220.00NisoloMen's Everyday Chukka Boots
9 9.5 10.5 11 11.5 12.5More details
Bloomingdale's$675.00Tod'sMen'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- SALE
Bloomingdale's$158.90$265.00Gordon RushMen's Austin Lace Up Chukka Boots
10 10.5 11 12 13More details - SALE
Bloomingdale's$276.50$395.00To BootMen's Dickens Chukka Boots
8.5 9.5 10 10.5 11 11.5 12 13More details 
Bloomingdale's$265.00Gordon RushMen's Austin Lace Up Chukka Boots
7 7.5 8 8.5 9 9.5 10 10.5 11.5 13More details- SALE
Bloomingdale's$126.00$180.00Bloomingdale'sMen's Suede Chukka Boots
7 7.5 8 8.5 9 9.5 10 10.5 11 11.5 12 13More details 
FARFETCH$95.00TimberlandRichmond Ridge chukka boot - Brown
5 6.5 7More details
FARFETCH$105.00TimberlandNewmarket II Chukka boots - Green
7 7.5 8More details- SALE
FARFETCH$206.00$511.00HereuAielo Sport leather chukka boots - Red
42 43 44More details 
Nordstrom$249.95EccoST.1 Hybrid Gore-Tex® Boot in Black at Nordstrom
7 8 10More details
Bloomingdale's$220.00NisoloMen's Everyday Chukka Boots
8 9.5 10.5 13More details
Bloomingdale's$150.00ClarksMen's Wallabee Chukka Boots
7 11 11.5 12More details
Saks Fifth Avenue$220.00Cole HaanMen's x Pendleton American Classics Leather Chukka Boots - Chestnut Acadia Plaid Caviar - Size 10 - Chestnut Acadia Plaid Caviar - Size 10
9.5 10More details- SALE
Saks Fifth Avenue$206.25$275.00VinceMen's Tacoma Leather Oxford Chukka Boots - Black - Size 7 - Black - Size 7
7 9More details - SALE
Saks Fifth Avenue$296.25$395.00To BootMen's Dickens Leather Chukka Boots - Windsor Moro - Size 8 - Windsor Moro - Size 8
8 10.5More details - SALE
Saks Fifth Avenue$51.71$68.95FlorsheimLittle Kid's & Kid's Navigator Jr. Leather Chukka Boots - Brown - Size 10 (Toddler) - Brown - Size 10 (Toddler)
10 (Toddler) 13 (Child)More details 
Karl Lagerfeld$269.00Karl LagerfeldUrano Iv Chukka Lace Boots, Man, , Size:
40 41 42 43 44 45 46More details
Karl Lagerfeld$269.00Karl LagerfeldUrano Iv Chukka Lace Boots, Man, , Size:
40 41 42 43 44 45 46More details
Karl Lagerfeld$269.00Karl LagerfeldUrano Iv Chukka Lace Boots, Man, , Size:
40 41 42 43 44 45 46More details
Karl Lagerfeld$269.00Karl LagerfeldUrano Iv Chukka Lace Boots, Man, , Size:
40 41 42 43 44 45 46More details
Karl Lagerfeld$269.00Karl LagerfeldUrano Iv Chukka Lace Boots, Man, , Size:
40 41 42 43 44 45 46More details
Karl Lagerfeld$269.00Karl LagerfeldUrano Iv Chukka Lace Boots, Man, , Size:
40 41 42 43 44 45 46More details- SALE
ECCO$164.99$175.00EccoMen's S. lite Hybrid Chukka Boot Size 5 Gore-tex
5 6 7 8 9 10 12More details 
ECCO$239.99EccoMen's ST. 1 Hybrid GTX Boot Size 5 Gore-tex
5 6 7 8 9More details- SALE
Hush Puppies$89.99$109.95Hush PuppiesMen's Detroit Chukka Boots, Size 8.5 Medium Width, Wine Suede
8.5 9 9.5 10 11 12More details - SALE
Hush Puppies$89.99$109.95Hush PuppiesMen's Detroit Chukka Boots, Size 7 Medium Width, Cognac Leather
7 7.5 8 8.5 9 10More details - SALE
Hush Puppies$89.99$109.95Hush PuppiesMen's Detroit Chukka Boots, Size 11 Wide Width, Black Leather
7.5 8 9 9.5 10 10.5 11 12 13More details - SALE
Hush Puppies$89.99$109.95Hush PuppiesMen's Detroit Chukka Boots, Size 7 Medium Width, Dark Brown Suede
7 7.5 8 8.5 9 9.5 10 10.5 11 11.5 12 13More details 
CAT Footwear$100.00CaterpillarMen's Transform 2.0 Boot Dark Beige, Size 7M
7 7.5 8 8.5 9 9.5 10 10.5 11 11.5 12 13More details
CAT Footwear$100.00CaterpillarMen's Narrate Chukka Boot Dachshund, Size 8M
8 8.5 9 9.5 10 10.5 11 11.5 12 13More details
Trouva$405.99Red WingRed Wing Chukka in Copper Rough and Tough Leather 03322D
leather | copper | 9 leather | copper | 10More details- SALE
Trouva$139.99$279.99SOLOVAIRSand Suede Chukka Boot
UK 07.5 / EU 41.5 UK 10.5 / EU 45More details 
Trouva$310.99YMCYogi Footwear Archer Leather Handcrafted In Portugal
36 39More details
Trouva$310.99YMCOlive Yogi Footwear Archer Leather Handcrafted In Portugal
36 42More details
Trouva$598.99BarkerCherry Grain Orkney
UK7/EU41 UK12/EU46More details
Trouva$440.99Red Wing3140 Classic Leather Chukka Boot Oro Iginal Tan
UK 7 UK 8More details
HBX$370.00Takahiromiyashita The SoloistFive Finger Chukka Boots
EU 42 EU 43 EU 44More details
Bloomingdale's$150.00ClarksMen's Wallabee Chukka Boots
8.5 9 12More details- SALE
Macy's$76.99$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 
SSENSE$1,555.00Takahiromiyashita The SoloistChukka Boots
8 9 10More details- SALE
Macy's$118.30$169.00Vince CamutoMen's Stuwert Casual Chukka Boot Men's Shoes
8 9 10.5 13More details - SALE
ECCO$139.99$175.00EccoMen's S. lite Hybrid Chukka Boot Size 5 Gore-tex
5 6 7 8 9 10 11 12 13More details 
Bloomingdale's$185.00sorelMen's Kezar Waterproof Chukka Boots
10 13More details- SALE
Hush Puppies$89.99$109.95Hush PuppiesMen's Detroit Chukka Boots, Size 9 Medium Width, Camo
9 10 10.5 11More details 
Nordstrom$160.00Josef SeibelEarl 04 Chukka Boot in Camel at Nordstrom
10 13More details
Marks & Spencer$139.00Marks & SpencerLeather Chukka Boots
US 6.5 US 7.5 US 8.5 US 9.5 US 10.5 US 11.5 US 12.5More details
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