Mens Chukka Boots

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41% Off

Original Penguin LEX CHUKKA BOOTOriginal Penguin LEX ...
$170.00$100.00
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Original Penguin MONTY CHUKKA BOOTOriginal Penguin MONTY ...
$110.00
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11% Off

Original Penguin MYLES CHUKKA BOOTOriginal Penguin MYLES ...
$190.00$170.00
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11% Off

Original Penguin MYLES CHUKKA BOOTOriginal Penguin MYLES ...
$190.00$170.00
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36% Off

Sharp  Ready Charson ChukkaSharp Ready Charson Chukka
$110.00$69.99
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20% Off

Ledge Hill 2 Lace Up ChukkaLedge Hill 2 Lace Up Chukka
$150.00$119.99
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60% Off

AP Hydro Chukka Boots For MenAP Hydro Chukka Boots ...
$50.00$20.00
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60% Off

AP Hydro Chukka Boots For MenAP Hydro Chukka Boots ...
$50.00$20.00
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75% Off

Cayman Chukka Boots For MenCayman Chukka Boots For Men
$79.99$20.00
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75% Off

Leather Chukka Boots - Factory 2nds For MenLeather Chukka Boots - ...
$174.95$43.00
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75% Off

Leather Chukka Boots - Factory 2nds For MenLeather Chukka Boots - ...
$174.95$43.00
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52% Off

Hanlan Chukka Boots - Leather For MenHanlan Chukka Boots - ...
$90.00$43.00
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52% Off

Hanlan Chukka Boots - Leather For MenHanlan Chukka Boots - ...
$90.00$43.00
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54% Off

Drake Chukka Boots - Vegan Leather For MenDrake Chukka Boots - ...
$109.00$49.99
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54% Off

Drake Chukka Boots - Vegan Leather For MenDrake Chukka Boots - ...
$109.00$49.99
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29% Off

Doran Chukka Boots - Nubuck For MenDoran Chukka Boots - ...
$70.00$49.99
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29% Off

Doran Chukka Boots - Nubuck For MenDoran Chukka Boots - ...
$70.00$49.99
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50% Off

Downtown Chukka Boots - Nubuck For MenDowntown Chukka Boots - ...
$120.00$59.99
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40% Off

Tough Bucks Chukka Boots - Waterproof, Leather For MenTough Bucks Chukka ...
$99.99$59.99
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33% Off

Hanlan Chukka Boots - Leather For MenHanlan Chukka Boots - ...
$90.00$59.99
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33% Off

Hanlan Chukka Boots - Leather For MenHanlan Chukka Boots - ...
$90.00$59.99
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33% Off

Chukka Boots - Leather For MenChukka Boots - Leather ...
$89.95$59.99
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33% Off

Chukka Boots - Leather For MenChukka Boots - Leather ...
$89.95$59.99
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42% Off

Cove Chukka Boots - Waterproof, Leather For MenCove Chukka Boots - ...
$120.00$69.99
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42% Off

Cove Chukka Boots - Waterproof, Leather For MenCove Chukka Boots - ...
$120.00$69.99
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36% Off

Camden Oxford Chukka Boots - Leather For MenCamden Oxford Chukka ...
$110.00$69.99
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22% Off

Navigator Chukka Boots - Nubuck For MenNavigator Chukka Boots -...
$90.00$69.99
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70% Off

Work Chukka Boots - Leather, Factory 2nds For MenWork Chukka Boots - ...
$260.00$79.00
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33% Off

Breccan Hayes Chukka Boots - Leather For MenBreccan Hayes Chukka ...
$119.99$79.99
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33% Off

Breccan Hayes Chukka Boots - Leather For MenBreccan Hayes Chukka ...
$119.99$79.99
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47% Off

World Vue Chukka Boots - Waterproof For MenWorld Vue Chukka Boots -...
$150.00$79.99
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47% Off

World Vue Chukka Boots - Waterproof For MenWorld Vue Chukka Boots -...
$150.00$79.99
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36% Off

Jake Chukka Boots - Leather For MenJake Chukka Boots - ...
$125.00$79.99
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36% Off

Jake Chukka Boots - Leather For MenJake Chukka Boots - ...
$125.00$79.99
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36% Off

Jake Chukka Boots - Leather For MenJake Chukka Boots - ...
$125.00$79.99
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29% Off

Frye Gates Chukka Boots - Leather For MenFrye Gates Chukka Boots ...
$140.00$99.99
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44% Off

1955 Original Modern Suburban Chukka Boots - Leather, Factory 2nds For Men1955 Original Modern ...
$179.99$99.99
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44% Off

1955 Original Modern Suburban Chukka Boots - Leather, Factory 2nds For Men1955 Original Modern ...
$179.99$99.99
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44% Off

1955 Original Modern Suburban Chukka Boots - Leather, Factory 2nds For Men1955 Original Modern ...
$179.99$99.99
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43% Off

Gold Cup Crepe Chukka Boots - Leather For MenGold Cup Crepe Chukka ...
$175.00$99.99
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78% Off

Chukka Boots - Leather For MenChukka Boots - Leather ...
$495.00$109.00
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37% Off

Morrys Chukka Boots For MenMorrys Chukka Boots For Men
$190.00$119.99
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35% Off

Pilot Chukka Boots - Suede For MenPilot Chukka Boots - ...
$199.95$129.99
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35% Off

Pilot Chukka Boots - Suede For MenPilot Chukka Boots - ...
$199.95$129.99
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50% Off

Mens IZOD Incent Chukka Boots 105 M, Dark NaturalMens IZOD Incent Chukka ...
$69.99$34.99
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18% Off

Mens ClarksR Vargo Mid Chukka Boots 12 M, Dark BrownMens ClarksR Vargo Mid ...
$109.99$89.99
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Mens ClarksR Bushacre 2 Chukka Ankle Boots 13 M, Wheat SuedeMens ClarksR Bushacre 2 ...
$100.00
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Mens Bostonian Desmin Chukka Ankle Boots 13 M, Cola SuedeMens Bostonian Desmin ...
$120.00
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50% Off

Mens Deer Stags James Chukka Boots - Olive 95 M, OliveMens Deer Stags James ...
$59.99$29.99
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50% Off

Mens Deer Stags James Chukka Boots - Black 95 M, BlackMens Deer Stags James ...
$59.99$29.99
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Mens Deer Stags Bangor Chukka Boots 95 M, Redwood/Dark BrownMens Deer Stags Bangor ...
$75.00
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Mens Deer Stags Rhodes Chukka Boots 95 M, Brown/BlueMens Deer Stags Rhodes ...
$75.00
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36% Off

Mens Florsheim Fenway Chukka Boots 95 D, Brown ChestnutMens Florsheim Fenway ...
$124.99$79.99
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5% Off

Mens Florsheim Comfortech Edge Chukka Boots 95 M, Navy NubuckMens Florsheim ...
$110.00$105.00
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5% Off

Mens Florsheim Union Plain Toe Chukka Boots 13 D, Black Crazy HorseMens Florsheim Union ...
$110.00$105.00
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4% Off

Mens Florsheim Midtown Waterproof Chukka Boots 14 D, BlackMens Florsheim Midtown ...
$125.00$120.00
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4% Off

Mens Florsheim Blaze Plain Toe Chukka Boots 8 D, CognacMens Florsheim Blaze ...
$130.00$125.00
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50% Off

Mens Nunn Bush Ozark Chukka Boots 12 M, TanMens Nunn Bush Ozark ...
$94.99$47.49
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6% Off

Mens Nunn Bush Galloway Chukka Boots 11 W, NavyMens Nunn Bush Galloway ...
$80.00$75.00
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6% Off

Mens Nunn Bush Lancaster Chukka Boots 10 W, CamelMens Nunn Bush ...
$90.00$85.00
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50% Off

Mens Skechers Droven-Evado Chukkas 85 M, BeigeMens Skechers Droven-...
$74.99$37.49
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43% Off

Mens Skechers Ryler Mobert Chukka Boots 95 M, BlackMens Skechers Ryler ...
$69.99$39.99
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Mens Spring Step Men Mathias Chukka Boots - Black 45, BlackMens Spring Step Men ...
$99.99
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Mens Spring Step Mathias Chukka Boots - Brown 41, BrownMens Spring Step ...
$99.99
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50% Off

Mens Stacy Adams Ashby Chukka Boots 105 M, CognacMens Stacy Adams Ashby ...
$104.99$52.49
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6% Off

Mens Stacy Adams Buckley Chukka Boots 95 M, Yellow SuedeMens Stacy Adams ...
$85.00$80.00
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43% Off

Mens MRC Maurice Chukka Boots 13 D, BordeauxMens MRC Maurice Chukka ...
$69.99$39.99
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40% Off

Mens Marco Vitale Evan Chukka Boots 13 D, BrownMens Marco Vitale Evan ...
$49.99$29.99
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25% Off

SM Mens Sawyer Brown Chukka Boot, 11SM Mens Sawyer Brown ...
$39.99$29.99
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33% Off

Route 66 Mens Bonneville Suede Chukka Boot - Black, 8Route 66 Mens ...
$39.99$26.99
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33% Off

Route 66 Mens Bonneville Suede Chukka Boot - Tan, 8Route 66 Mens ...
$39.99$26.99
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25% Off

Route 66 Mens Bonneville Suede Chukka Boot - Gray, 95109710585137512118Route 66 Mens ...
$39.99$29.99
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Vionic Mens Leather Chukka Style Boots - Bowery ChaseVionic Mens Leather ...
$160.00
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HELM Boots Mens Chukka Leather Boot - PeteHELM Boots Mens Chukka ...
$104.29
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60% Off

Structure Mens Alvin Leather Chukka Boot - Black, Size 85Structure Mens Alvin ...
$75.00$30.00
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29% Off

Structure Mens Barclay Black Chukka Boot, Size 11Structure Mens Barclay ...
$70.00$49.99
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28% Off

Structure Mens Lionel Brown Chukka Boot, Size 75Structure Mens Lionel ...
$70.00$50.18
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43% Off

Thom McAn Mens Warren Black Chukka Boot, Size 95Thom McAn Mens Warren ...
$70.00$39.99
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43% Off

Thom McAn Mens Wayne Brown Chukka Boot, Size 12Thom McAn Mens Wayne ...
$70.00$39.99
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67% Off

J75 by Jump Mens Ireland Navy Blue Ankle Chukka Boot, Size 12J75 by Jump Mens ...
$90.00$30.00
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SM New York Mens Keaton Black Chukka Boot, Size 9SM New York Mens Keaton ...
$60.00
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SM New York Mens Carlton Brown Chukka Boot, Size 95SM New York Mens ...
$60.00
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SM New York Mens Brock Gray Chukka Boot, Size 12SM New York Mens Brock ...
$60.00
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29% Off

Timberland PRO Mens Disruptor Alloy Toe Chukka Boot A1BAK - Wheat, Size 105, TanTimberland PRO Mens ...
$140.00$99.99
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25% Off

DieHard Mens Soft Toe Chukka Work Boot - Brown, Size 105DieHard Mens Soft Toe ...
$100.00$74.99
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21% Off

Caterpillar Cat Footwear Mens Transform Leather Chukka Boot - Brown, Size 10Caterpillar Cat ...
$95.00$74.99
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24% Off

Nunn Bush Mens Rawson Brown Chukka Boot, Size 115Nunn Bush Mens Rawson ...
$90.00$67.99
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22% Off

Nunn Bush Mens Marley Street Brown Chukka Boot, Size 10, BlackNunn Bush Mens Marley ...
$95.00$73.99
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13% Off

Skidbuster Mens Leather Slip-Resistant 05073 Chukka Work Boot - Black, Size 95Skidbuster Mens Leather ...
$80.00$69.99
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29% Off

Lugz Mens Sandstone Brown Chukka Boot, Size 9Lugz Mens Sandstone ...
$85.00$59.99
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29% Off

Lugz Mens Sandstone Chukka Boot - Black, Size 8, BrownLugz Mens Sandstone ...
$85.00$59.99
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Georgia Boot Mens Leather 5 Chukka Wedge Work Boot Wide Width Available - Brown, Size 75, Barracuda GoldGeorgia Boot Mens ...
$124.99$123.99
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55% Off

Giorgio Armani - Microhole Chukka Boot Night Mens BootsGiorgio Armani - ...
$595.00$269.99
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50% Off

John Varvatos - Star Chukka Boot Antique Mens BootsJohn Varvatos - Star ...
$228.00$114.99
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43% Off

John Varvatos - Mick Crepe Chukka Lead Mens BootsJohn Varvatos - Mick ...
$248.00$141.25
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50% Off

John Varvatos - Julian Chukka Brownstone Mens Lace-up BootsJohn Varvatos - Julian ...
$498.00$249.99
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60% Off

Bogs - Johnny Chukka II Coffee Mens BootsBogs - Johnny Chukka II ...
$155.00$62.00
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34% Off

Bogs - Johnny Chukka Scotch Mens Lace-up BootsBogs - Johnny Chukka ...
$155.00$102.63
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34% Off

Chaco - Montrose Chukka Bone Brown Mens Lace-up BootsChaco - Montrose Chukka ...
$139.95$92.68
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45% Off

Crocs - CitiLane Roka Chukka Black/White Mens BootsCrocs - CitiLane Roka ...
$59.99$32.99
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