Chukka Boots

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Mens Chukka Boots

Enjoy our unique selection of men's chukka boots and find the right footwear for your wardrobe. You should look good in your chukka boots and we want to help.

Il Gergo Boss Suede Chukka Boot Dark Brown
Il Gergo Boss Suede Chukka Boot Dark Brown
$638.00
10% Off, Use Code GOLD10
Spernanzoni Conte Leather Chukka Boot Antique Espresso
Spernanzoni Conte Leather Chukka Boot Antique Espresso
$971.00
10% Off, Use Code GOLD10
Bruno Magli Cat Walk Suede Chukka Boot Taupe
Bruno Magli Cat Walk Suede Chukka Boot Taupe
$350.00
Alan Payne Bravo II Suede Chukka Boot Truffle
Alan Payne Bravo II Suede Chukka Boot Truffle
$195.00
10% Off, Use Code GOLD10
Belvedere Studio Axel Genuine Italian Deerskin Chukka Boots Brown
Belvedere Studio Axel Genuine Italian Deerskin Chukka Boots Brown
$379.00
10% Off, Use Code GOLD10
Belvedere Studio Axel Genuine Italian Deerskin Chukka Boots Black
Belvedere Studio Axel Genuine Italian Deerskin Chukka Boots Black
$379.00
10% Off, Use Code GOLD10
Bruno Magli Mabelton Suede Chukka Boot Cognac
Bruno Magli Mabelton Suede Chukka Boot Cognac
$270.00
Zelli Campo High Italian Sueded Goatskin Chukka Boot Taupe
Zelli Campo High Italian Sueded Goatskin Chukka Boot Taupe (46-605-TPE)
$695.00
10% Off, Use Code GOLD10
Zelli Campo High Italian Sueded Goatskin Chukka Boot Nicotine
Zelli Campo High Italian Sueded Goatskin Chukka Boot Nicotine (46-605-NIC)
$695.00
10% Off, Use Code GOLD10
TB Phelps Woodson Leather Chukka Boot Old Briar
TB Phelps Woodson Leather Chukka Boot Old Briar
$300.00
10% Off, Use Code GOLD10
Mauri 4994/1 Alligator Chukka Boots Solid Gold
Mauri 4994/1 Alligator Chukka Boots Solid Gold
$870.00
10% Off, Use Code GOLD10
Corrente C0301-5786 Bit Buckle Ankle Boots Navy
Corrente C0301-5786 Bit Buckle Ankle Boots Navy
$369.00
10% Off, Use Code GOLD10
Corrente C030-5786 Bit Buckle Ankle Boots Tan
Corrente C030-5786 Bit Buckle Ankle Boots Tan
$369.00
10% Off, Use Code GOLD10
Paul Parkman Woven Leather Chukka Boots Green & Purple
Paul Parkman Woven Leather Chukka Boots Green & Purple
$771.00
10% Off, Use Code GOLD10
Marco Di Milano Pietro Alligator Chukka Boots Newspaper
Marco Di Milano Pietro Alligator Chukka Boots Newspaper
$850.00 $750.00
10% Off, Use Code GOLD10
Corrente C185-7520 Shearling Chukka Boot Black
Corrente C185-7520 Shearling Chukka Boot Black
$389.00
10% Off, Use Code GOLD10
Corrente C186-7520 Shearling Chukka Boot Brown
Corrente C186-7520 Shearling Chukka Boot Brown
$389.00
10% Off, Use Code GOLD10
Corrente C187-7520 Shearling Chukka Boot Navy
Corrente C187-7520 Shearling Chukka Boot Navy
$389.00
10% Off, Use Code GOLD10
Firmani Asher Leather Shoes Brandy
Firmani Asher Leather Shoes Brandy
$229.00 $180.00
10% Off, Use Code GOLD10
Firmani Asher Leather Shoes Black
Firmani Asher Leather Shoes Black
$229.00 $180.00
10% Off, Use Code GOLD10
Marco Di Milano Pietro Alligator Chukka Boots Honey
Marco Di Milano Pietro Alligator Chukka Boots Honey
$850.00 $750.00
10% Off, Use Code GOLD10
Marco Di Milano Pietro Alligator Chukka Boots Rustic Jean
Marco Di Milano Pietro Alligator Chukka Boots Blue Jean
$850.00 $750.00
10% Off, Use Code GOLD10
Marco Di Milano Martinelli Caiman Crocodile Chukka Boots Black
Marco Di Milano Martinelli Caiman Crocodile Chukka Boots Black
$720.00 $625.00
10% Off, Use Code GOLD10
Marco Di Milano Martinelli Caiman Crocodile Chukka Boots Navy
Marco Di Milano Martinelli Caiman Crocodile Chukka Boots Navy
$720.00 $625.00
10% Off, Use Code GOLD10
Mauri 2700 Alligator / Time Chukka Boots Sport Rust
Mauri 2700 Alligator / Time Chukka Boots Sport Rust
$556.00 $528.00
10% Off, Use Code GOLD10
Ugo Vasare David Lama & Leather Rugged Boots Brown
Ugo Vasare David Lama & Leather Rugged Boots Brown
$470.00
Calzoleria Toscana Croci Suede Ankle Demi Boot Brown
Calzoleria Toscana Croci Suede Ankle Demi Boot Dark Brown
From $498.00
Allen Edmonds Chandler Chukka Boot Antique Hickory (6035)
Allen Edmonds Chandler Chukka Boot Antique Hickory (6035)
$525.00
10% Off, Use Code GOLD10
Allen Edmonds Chandler Weatherproof Chukka Boot Pecan (6690)
Allen Edmonds Chandler Weatherproof Chukka Boot Pecan (6690)
$525.00
10% Off, Use Code GOLD10
Allen Edmonds Chandler Weatherproof Chukka Boot Teak (6693)
Allen Edmonds Chandler Weatherproof Chukka Boot Teak (6693)
$525.00
10% Off, Use Code GOLD10
Zelli Marco Italian Suede Chukka Boots Grey
Zelli Marco Italian Suede Chukka Boots Grey (46-592-GRY)
$695.00 $386.10
10% Off, Use Code GOLD10
Zelli Rezza Italian Suede Chukka Boot Black
Zelli Rezza Italian Suede Chukka Boot Black (46-602-BLK)
$695.00
10% Off, Use Code GOLD10
Vinci Leather The Kagan Navy Wingtip Chukka Sneaker Boot (3836.58)
Vinci Leather The Kagan Navy Wingtip Chukka Sneaker Boot (3836.58)
$650.00 $512.00
10% Off, Use Code GOLD10
Vinci Leather The Kagan Brown Wingtip Chukka Sneaker Boot (3836.58)
Vinci Leather The Kagan Brown Wingtip Chukka Sneaker Boot (3836.58)
$650.00 $512.00
10% Off, Use Code GOLD10
Vinci Leather The Kagan Black Wingtip Chukka Sneaker Boot (3836.58)
Vinci Leather The Kagan Black Wingtip Chukka Sneaker Boot (3836.58)
$650.00 $512.00
10% Off, Use Code GOLD10
Mauri 3216 Pyro Time/ Baby Croc/ Mauri Fabric/ Nappa Boots Red / Taupe
Mauri 3216 Pyro Time/ Baby Croc/ Mauri Fabric/ Nappa Boots Red / Taupe
$390.00 $366.60
10% Off, Use Code GOLD10

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