- Chukka Boots
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Macy's$110.00ClarksMen's Bushacre 2 Chukka Boots Men's Shoes
8 8.5 9 9.5 9.5W 10 10.5 10.5W 10W 11 11.5 12 13More details
Macy's$110.00ClarksMen's Bushacre 2 Chukka Boots Men's Shoes
8 8W 9 9W 11.5W 13More details
Macy's$115.00Nunn BushMen's Luxor Water-Resistant Plain Toe Chukka Boots Men's Shoes
8.5M 8XW 9.5XW 9M 9XW 10.5M 10.5XW 10M 11XW 12XWMore details
Macy's$79.99NauticaMen's Largo Chukka Boots Men's Shoes
7.5M 8.5M 8M 9.5M 9M 10.5M 10M 11M 12M 13MMore details
Macy's$90.00Steve MaddenMen's Hestonn Chukka Boots Men's Shoes
7.5M 7M 8.5M 8M 9.5M 9M 10.5M 10M 11.5M 11M 12M 13MMore details
Macy's$104.95PropetMen's Finn Oxfords Boots Men's Shoes
10.5 5E 10.5M 13W 13XWMore details- OUTLET
Macy's$74.99$149.99Thomas & VineMen's Keegan Wide Width Plain Toe Chukka Boot Men's Shoes
8.5W 8W 9.5W 9W 10.5W 10W 11.5W 11W 12W 13W 14WMore details - OUTLET
Macy's$59.99$119.99Vance Co.Men's Redford Tru Comfort Foam Lace-Up Cap Toe Chukka Boot Men's Shoes
8.5M 8M 9.5M 9M 10.5M 10M 11.5M 11M 12M 13MMore details 
Macy's$200.00BarbourMen's Readhead Two-Eyelet Chukka Boot Men's Shoes
8 10 12More details- OUTLET
Macy's$78.00$130.00ReservedMen's Keon Chukka Boots Men's Shoes
8.5M 8M 9.5M 9M 10.5M 10M 11M 12M 13MMore details - OUTLET
Macy's$42.50$85.00Vance Co.Austin Men's Cap Toe Chukka Boot Men's Shoes
8M 9.5M 9M 10.5M 11M 12MMore details - OUTLET
Macy's$74.99$149.99Thomas & VineMen's Keegan Plain Toe Chukka Boot Men's Shoes
8.5M 8M 9M 10.5M 10M 11.5M 11M 13MMore details 
Macy's$165.00Johnston & MurphyMen's Upton Chukka Boots Men's Shoes
9.5M 14MMore details
END$355.00GRENSONMen's Clement Chukka Boot in , Size | END. Clothing
UK 6 UK 7 UK 8 UK 9 UK 11More details
END$355.00Drake'sMen's Crosby Moc Toe Boot in , Size | END. Clothing
UK 6 UK 7 UK 8 UK 9 UK 11More details
Selfridges & Co$405.00Officine creativeMens Kent Suede Chukka Boots 7
7 8 9 10 11More details
END$189.00YogiMen's Hitch Suede Boot in , Size | END. Clothing
UK 6 UK 9More details- OUTLET
ASOS$49.50$90.00River IslandChukka boots in stone
7 8 9 10 11 13More details
Trouva$265.99LoakeNubuck Gilbert Chukka Shoes
41 42 43 44 45More 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
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
Saks Fifth Avenue$1,550.00Stefano RicciMen's Suede Chukka Boots - Black - Size 6 - Black - Size 6
6 7 8 9 10More 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- OUTLET
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$279.99Yogi FootwearWinstone Crepe Leather Handcrafted In Portugal
36 38 40 41More details
Trouva$295.49Yogi FootwearLucas Tumbled Leather Moccasin Vibram Boot Handcrafted In Portugal
40 41 42More 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
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$790.00santoniMen's Detroit Laceless Chukka Boots
8 8.5 10More details
Saks Fifth Avenue$220.00Cole HaanMen's x Pendleton American Classics Leather Chukka Boots - Chestnut Acadia Plaid Caviar - Size 11 - Chestnut Acadia Plaid Caviar - Size 11
7 8 9 9.5 11More 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 8.5 9 9.5 10 10.5 11 11.5 13More details- OUTLET
Saks Fifth Avenue$296.25$395.00To BootMen's Dickens Leather Chukka Boots - Softy Blue - Size 6 - Softy Blue - Size 6
6 6.5 7 7.5 8 8.5 9 9.5 10.5 11More details 
Saks Fifth Avenue$139.95UGGMen's Neumel Suede Chukka Boots - Chestnut - Size 7 - Chestnut - Size 7
7 8 10 11 12 13More details- OUTLET
Saks Fifth Avenue$51.71$68.95FlorsheimLittle Kid's & Kid's Navigator Jr. Leather Chukka Boots - Brown - Size 10 (Toddler) - Brown - Size 10 (Toddler)
3 (Child) 10 (Toddler) 11 (Child) 12 (Child) 13 (Child)More details 
Saks Fifth Avenue$139.95UGGMen's Neumel Suede Chukka Boots - Black - Size 7 - Black - Size 7
7 8 9 10 11 12 13More details- OUTLET
Bloomingdale's$332.50$475.00To BootMen's Major Chukka Boots
8 9.5 10.5 13More details 
Bloomingdale's$220.00NisoloMen's Everyday Chukka Boots
8.5 9.5 10 11.5More details
Bloomingdale's$220.00NisoloMen's Everyday Chukka Boots
8 9.5 10.5 13More details
Nordstrom$220.00ASPORTUGUESAS BY FLY LONDONCody Wool Chukka Boot in 004 Black Tweed/Felt at Nordstrom
6 7 8 9 10More details
Bloomingdale's$140.00UGGMen's Neumel Suede Chukka Boots
8 9 12 13More details
Nordstrom$160.00Josef SeibelEarl 04 Chukka Boot in Camel at Nordstrom
8 10 11 12 13More details- OUTLET
Bloomingdale's$243.75$325.00Kenneth ColeMen's Albert Lace Up Chukka Boots
8 9.5 11 12More 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) 10 (Toddler)More details- OUTLET
Saks Fifth Avenue$296.25$395.00To BootMen's Dickens Leather Chukka Boots - Windsor Moro - Size 7.5 - Windsor Moro - Size 7.5
7.5 8.5 9 10.5More details - OUTLET
Saks Fifth Avenue$104.96$139.95UGGMen's Neumel Suede Chukka Boots - Samba Red - Size 7 - Samba Red - Size 7
7 8 9 14More details 
Bloomingdale's$220.00GeoxMen's Brayden 2Fit Abx Waterproof Lace Up Chukka Boots
8US / 41EU 10US / 43EU 12US / 45EUMore details
Bloomingdale's$780.00santoniMen's Detroit Laceless Chukka Boots
9.5 10 11More details
Bloomingdale's$720.00santoniMen's Detroit Laceless Chukka Boots
8 9 12More details- OUTLET
Bloomingdale's$126.00$180.00Bloomingdale'sMen's Suede Chukka Boots
9 11.5 13More details 
Bloomingdale's$140.00UGGMen's Neumel Suede Chukka Boots
9 10 11More 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
Trouva$405.99Red WingRed Wing Chukka in Copper Rough and Tough Leather 03322D
leather | copper | 9 leather | copper | 10More details- OUTLET
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
Bloomingdale's$265.00Gordon RushMen's Austin Lace Up Chukka Boots
10 11More details
Bloomingdale's$675.00Tod'sMen's Polacco Chukka Boots
8UK / 9US 11UK / 12USMore details
Bloomingdale's$220.00NisoloMen's Everyday Chukka Boots
9.5 11More details
Bloomingdale's$780.00santoniMen's Detroit Laceless Chukka Boots
8.5 9.5More details
Bloomingdale's$675.00Tod'sMen's Polacco Chukka Boots
9UK / 10US 10.5UK / 11.5USMore details- OUTLET
Bloomingdale's$158.90$265.00Gordon RushMen's Austin Lace Up Chukka Boots
10 10.5More details - OUTLET
Bloomingdale's$276.50$395.00To BootMen's Dickens Chukka Boots
11 13More details 
Bloomingdale's$150.00ClarksMen's Wallabee Chukka Boots
7 11More details
Bloomingdale's$265.00Gordon RushMen's Austin Lace Up Chukka Boots
8 9.5More details
Bloomingdale's$170.00sorelMen's Caribou Mod Chukka Waterproof Boots
7 8More details
Bloomingdale's$170.00sorelMen's Caribou Mod Chukka Waterproof Boots
7 8More details
Bloomingdale's$140.00UGGMen's Neumel Suede Chukka Boots
7 12More details
Nordstrom$249.95EccoST.1 Hybrid Gore-Tex® Boot in Nutmeg Brown at Nordstrom
6 7 8 9 10 11 12 13 14More details
Nordstrom$249.95EccoST.1 Hybrid Gore-Tex® Boot in Black at Nordstrom
6 7 8 9 10 11 12 13 14More details
Saks Fifth Avenue$275.00VinceMen's Tacoma Leather Oxford Chukka Boots - Black - Size 11 - Black - Size 11
9 11More details
Saks Fifth Avenue$2,350.00CORTHAYMen's Chukka Pullman Suede Boots - Dark Brown - Size 10 - Dark Brown - Size 10
8.5 10More details- OUTLET
Saks Fifth Avenue$54.71$72.95FlorsheimLittle Boy's & Boy's Supacush Chukka Boots - Brown - Size 10 (Toddler) - Brown - Size 10 (Toddler)
10 (Toddler) 12 (Child)More details - OUTLET
Nordstrom$145.00$220.00ASPORTUGUESAS BY FLY LONDONCody Wool Chukka Boot in 005 Indigo Blue Tweed/Felt at Nordstrom
6 9More details - OUTLET
Nordstrom$145.00$220.00ASPORTUGUESAS BY FLY LONDONCody Wool Chukka Boot in 000 Concrete Tweed/Felt at Nordstrom
6 7More details 
Trouva$221.99TimberlandBradstreet Chukka Boot Olive Full Grain Leather
UK 10More details
Trouva$283.49Yogi FootwearHitch Tumbled Leather Boot Olive
40More details
Trouva$434.49Sanders & SandersDirty Buck Hi Top Suede Chukka Boots
UK7More details
Trouva$440.99Red Wing3141 Classic Leather Chukka Boot Briar Oil Slick Brown
UK 8More details
Trouva$434.49Sanders & SandersNavy Hi Top Suede Chukka Boots
UK8More details
Trouva$440.99Red WingBrown Wing Chukka Boot 3141
UK7More details
Bloomingdale's$185.00sorelMen's Kezar Waterproof Chukka Boots
13More details
Bloomingdale's$450.00Bruno MagliMen's Vicolo Lace Up Chukka Boots
11More details
Macy's$90.00Steve MaddenMen's Harken Chukka Boots Men's Shoes
7 7.5 8 8.5 9 9.5 10 10.5 11 11.5 12 13More details
Macy's$165.95Anthony VeerMen's George Suede Lace-Up Chukka Boots Men's Shoes
15D 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 D US 14 DMore details
Macy's$165.95Anthony VeerMen's George Suede Lace-Up Chukka Boots Men's Shoes
15D 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 D US 14 DMore details
Macy's$145.95Anthony VeerMen'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
Macy's$150.00UGGMen's Neumel Classic Chukka Boots Men's Shoes
7 8 9 10 11 12 13More details
Macy's$210.00Eastland ShoeMen's Oscar Chukka Boots Men's Shoes
8.5M 8M 9.5M 9M 10.5M 10M 11.5M 11M 12M 13MMore details
Macy's$169.00Vince CamutoMen's Saveli Casual Chukka Boot Men's Shoes
8 8.5 9 9.5 10 10.5 11 11.5 12 13More details
Bloomingdale's$265.00Gordon RushMen's Austin Lace Up Chukka Boots
11.5More details
Bloomingdale's$450.00Bruno MagliMen's Vicolo Lace Up Chukka Boots
11More details
Bloomingdale's$150.00ClarksMen's Wallabee Chukka Boots
8.5More details
Bloomingdale's$160.00sorelMen's Kezar Waterproof Lace Up Moc Toe Chukka Boots
7More details
Bloomingdale's$185.00sorelMen's Kezar Waterproof Chukka Boots
7More details- OUTLET
Bloomingdale's$243.75$325.00Kenneth ColeMen's Albert Lace Up Chukka Boots
9More details - OUTLET
Bloomingdale's$224.00$320.00Cole HaanMen's 2.ZERGRAND Lace Up Chukka Boots
10 MMore details - OUTLET
ECCO$164.99$175.00EccoMen's S. lite Hybrid Chukka Boot Size 5 Gore-tex
5 6 7 8 9 10 11 12More details 
ECCO$239.99EccoMen's ST. 1 Hybrid GTX Boot Size 5 Gore-tex
5 6 7 8 9More details- OUTLET
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 
FARFETCH$620.00Onitsuka TigerX Nick Wooster Chukka boots - White
26 26.5 27 27.5 28More details
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