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Men's Winter Chukka Boots

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  • Ariat
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  • 29 Items
Men's Chukka Lug Suede BootsMen's Chukka Lug Suede Boots
Quick View

UGGMen's Chukka Lug Suede Boots

Permanently Reduced
Orig. $150.00
Now $75.00
Men's Lug Chukka BootsMen's Lug Chukka Boots
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UGGMen's Lug Chukka Boots

Permanently Reduced
Orig. $130.00
Now $65.00
Full StarFull StarFull StarFull StarFull Star(1)
Men's Chukka Hiker Waterproof BootsMen's Chukka Hiker Waterproof Boots
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Twisted XMen's Chukka Hiker Waterproof Boots

$174.95
Full StarFull StarFull StarFull StarFull Star(1)
Men's Harrison Leather Chukka BootsMen's Harrison Leather Chukka Boots
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BornMen's Harrison Leather Chukka Boots

$145.00
Full StarFull StarFull StarFull StarHalf Star(33)
Men's Morse Leather Chukka BootsMen's Morse Leather Chukka Boots
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Cole HaanMen's Morse Leather Chukka Boots

$148.00
Men's Upton Leather Chukka BootsMen's Upton Leather Chukka Boots
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Johnston & MurphyMen's Upton Leather Chukka Boots

Permanently Reduced
Orig. $179.00
Now $119.99
Men's Driving Leather Moc Toe Chukka BootsMen's Driving Leather Moc Toe Chukka Boots
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Twisted XMen's Driving Leather Moc Toe Chukka Boots

$139.95
Men's Calder Leather Chukka Lace Up BootsMen's Calder Leather Chukka Lace Up Boots
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Johnston & MurphyMen's Calder Leather Chukka Lace Up Boots

$179.00
Full StarFull StarFull StarFull StarHalf Star(53)
Men's Newmarket Chukka Leather BootsMen's Newmarket Chukka Leather Boots
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TimberlandMen's Newmarket Chukka Leather Boots

$140.00
Full StarFull StarFull StarFull StarHalf Star(15)
Men's Illiad Leather Chukka BootsMen's Illiad Leather Chukka Boots
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Bed StuMen's Illiad Leather Chukka Boots

$209.00
Men's Asher Suede Chukka BootsMen's Asher Suede Chukka Boots
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Polo Ralph LaurenMen's Asher Suede Chukka Boots

Permanently Reduced
Orig. $198.00
Now $132.66
Men's Madson II Waterproof Leather Chukka BootsMen's Madson II Waterproof Leather Chukka Boots
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SorelMen's Madson II Waterproof Leather Chukka Boots

$190.00
Full StarFull StarFull StarFull StarEmpty Star(88)
Men's Waterproof Driving Moccasins Chukka BootsMen's Waterproof Driving Moccasins Chukka Boots
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Twisted XMen's Waterproof Driving Moccasins Chukka Boots

$159.95
Internet Exclusive
Full StarFull StarFull StarFull StarHalf Star(3)
Men's Neumel Classic Fur Lined Suede Lace Up Chukka BootsMen's Neumel Classic Fur Lined Suede Lace Up Chukka Boots
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UGGMen's Neumel Classic Fur Lined Suede Lace Up Chukka Boots

$150.00
Full StarFull StarFull StarFull StarHalf Star(354)
Men's Redwood Falls Waterproof Leather Chukka BootsMen's Redwood Falls Waterproof Leather Chukka Boots
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TimberlandMen's Redwood Falls Waterproof Leather Chukka Boots

Permanently Reduced
Orig. $135.00
Now $90.45
Internet Exclusive
Full StarFull StarFull StarFull StarEmpty Star(67)
Men's Braxton Oiled Leather Chukka BootsMen's Braxton Oiled Leather Chukka Boots
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Johnston & MurphyMen's Braxton Oiled Leather Chukka Boots

Permanently Reduced
Orig. $159.00
Now $119.99
Full StarFull StarFull StarFull StarFull Star(1)
Men's Chamberlin Water Resistant Nubuck Chukka BootsMen's Chamberlin Water Resistant Nubuck Chukka Boots
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Cole HaanMen's Chamberlin Water Resistant Nubuck Chukka Boots

$150.00
Internet Exclusive
Men's Larkin Leather Plain Toe Chukka BootsMen's Larkin Leather Plain Toe Chukka Boots
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Johnston & MurphyMen's Larkin Leather Plain Toe Chukka Boots

Permanently Reduced
Orig. $159.00
Now $99.99
Full StarFull StarFull StarFull StarEmpty Star(10)
Men's XC+Parker Waterproof Leather Chukka BootsMen's XC+Parker Waterproof Leather Chukka Boots
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Johnston & MurphyMen's XC+Parker Waterproof Leather Chukka Boots

Permanently Reduced
Orig. $189.00
Now $129.99
Full StarFull StarFull StarFull StarHalf Star(7)
Men's Metropole Milan Suede Chukka BootsMen's Metropole Milan Suede Chukka Boots
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ECCOMen's Metropole Milan Suede Chukka Boots

$195.00
Men's Slabtown 62' Stoic Suede Chukka BootsMen's Slabtown 62' Stoic Suede Chukka Boots
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SorelMen's Slabtown 62' Stoic Suede Chukka Boots

$160.00
Internet Exclusive
Full StarFull StarFull StarFull StarFull Star(1)
Men's Split Rock Leather Moc Toe Chukka BootsMen's Split Rock Leather Moc Toe Chukka Boots
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AriatMen's Split Rock Leather Moc Toe Chukka Boots

$189.95
Full StarFull StarFull StarFull StarFull Star(2)
Men's Calder 175th Anniversary Leather Chukka BootsMen's Calder 175th Anniversary Leather Chukka Boots
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Johnston & MurphyMen's Calder 175th Anniversary Leather Chukka Boots

Permanently Reduced
Orig. $179.00
Now $119.99
Full StarFull StarFull StarFull StarEmpty Star(3)
Men's Tabriz Lace Up Leather Chukka BootsMen's Tabriz Lace Up Leather Chukka Boots
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Steve MaddenMen's Tabriz Lace Up Leather Chukka Boots

Permanently Reduced
Orig. $140.00
Now $89.99
Men's Allagash Handsewn Leather Chukka BootsMen's Allagash Handsewn Leather Chukka Boots
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L.L.BeanMen's Allagash Handsewn Leather Chukka Boots

Permanently Reduced
Orig. $180.00
Now $120.60
Full StarFull StarFull StarHalf StarEmpty Star(37)
Men's Ayden Moc Toe Waterproof Leather Lace Up Chukka BootsMen's Ayden Moc Toe Waterproof Leather Lace Up Chukka Boots
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Flag LTD.Men's Ayden Moc Toe Waterproof Leather Lace Up Chukka Boots

Permanently Reduced
Orig. $175.00
Now $87.50
Dillard´s Exclusive
Men's Eco Bay Nubuck Chukka BootsMen's Eco Bay Nubuck Chukka Boots
Quick View

L.L.BeanMen's Eco Bay Nubuck Chukka Boots

Permanently Reduced
Orig. $130.00
Now $87.10
Full StarFull StarFull StarFull StarHalf Star(4)
Men's Driving CellStretch Leather Moc Toe Chukka BootsMen's Driving CellStretch Leather Moc Toe Chukka Boots
Quick View

Twisted XMen's Driving CellStretch Leather Moc Toe Chukka Boots

$159.95
Full StarFull StarEmpty StarEmpty StarEmpty Star(1)
Men's Earl 04 Leather Lace Up Chukka BootsMen's Earl 04 Leather Lace Up Chukka Boots
Quick View

Josef SeibelMen's Earl 04 Leather Lace Up Chukka Boots

$180.00
Full StarFull StarFull StarFull StarFull Star(6)
  • 29 Items

About Men's Winter Chukka Boots

Discover the perfect blend of style and functionality with our collection of men's winter chukka boots. Designed to provide warmth and comfort, these boots feature durable materials and weather-resistant properties, making them ideal for cold, wet conditions. With a variety of styles, including lace-up and slip-on options, you can find the perfect fit for any occasion.

Our men's winter chukka boots are crafted with supportive soles and cushioned insoles, ensuring all-day comfort whether you're navigating city streets or enjoying outdoor adventures. The versatile designs easily pair with casual or smart-casual outfits, making them a must-have addition to your winter wardrobe.

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