Mens Boots

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12% Off

Original Penguin LEX CHUKKA BOOTOriginal Penguin LEX ...
$170.00$150.00
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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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Original Penguin MONTY CHUKKA BOOTOriginal Penguin MONTY ...
$185.00
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Original Penguin MONTY CHUKKA BOOTOriginal Penguin MONTY ...
$185.00
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70% Off

AP Hydro Chukka Boots For MenAP Hydro Chukka Boots ...
$50.00$15.00
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68% Off

Hanlan Chukka Boots - Leather For MenHanlan Chukka Boots - ...
$90.00$29.00
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44% Off

Doran Chukka Boots - Nubuck For MenDoran Chukka Boots - ...
$70.00$39.00
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44% Off

Doran Chukka Boots - Nubuck For MenDoran Chukka Boots - ...
$70.00$39.00
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57% Off

Tough Bucks Chukka Boots - Waterproof, Leather For MenTough Bucks Chukka ...
$99.99$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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59% Off

Cove Chukka Boots - Waterproof, Leather For MenCove Chukka Boots - ...
$120.00$49.00
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59% Off

Cove Chukka Boots - Waterproof, Leather For MenCove Chukka Boots - ...
$120.00$49.00
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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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51% Off

Breccan Hayes Chukka Boots - Leather For MenBreccan Hayes Chukka ...
$119.99$59.00
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51% Off

Breccan Hayes Chukka Boots - Leather For MenBreccan Hayes Chukka ...
$119.99$59.00
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61% Off

World Vue Chukka Boots - Waterproof For MenWorld Vue Chukka Boots -...
$150.00$59.00
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53% Off

Jake Chukka Boots - Leather For MenJake Chukka Boots - ...
$125.00$59.00
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53% Off

Jake Chukka Boots - Leather For MenJake Chukka Boots - ...
$125.00$59.00
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53% Off

Jake Chukka Boots - Leather For MenJake Chukka Boots - ...
$125.00$59.00
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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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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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57% Off

Gold Cup Crepe Chukka Boots - Leather For MenGold Cup Crepe Chukka ...
$175.00$75.00
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58% Off

Morrys Chukka Boots For MenMorrys Chukka Boots For Men
$190.00$79.00
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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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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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41% Off

Classic Chukka Boots - Leather, Factory 2nds For MenClassic Chukka Boots - ...
$270.00$159.99
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41% Off

Classic Chukka Boots - Leather, Factory 2nds For MenClassic Chukka Boots - ...
$270.00$159.99
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41% Off

Classic Chukka Boots - Leather, Factory 2nds For MenClassic Chukka Boots - ...
$270.00$159.99
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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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49% Off

Express Mens Leather Chukka BootExpress Mens Leather ...
$138.00$69.99
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49% Off

Express Mens Textured Leather Chukka BootsExpress Mens Textured ...
$138.00$69.99
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Express Mens Dark Brown Leather Chukka BootsExpress Mens Dark Brown ...
$138.00
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Express Mens Leather Chukka BootsExpress Mens Leather ...
$138.00
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63% Off

Clarks Mens Bushacre Chukka Boot - Beeswax - Size 12Clarks Mens Bushacre ...
$100.00$37.29
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42% Off

Clarks Mens Vargo Rise Chukka Boot - Dark Brown - Size 12Clarks Mens Vargo Rise ...
$110.00$63.29
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69% Off

Timberland Womens Nellie Waterproof Chukka Boot - Black - Size 9Timberland Womens ...
$142.99$44.79
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50% Off

Timberland Mens Fly Roam Go Chukka Boots - Burgundy - Size95Timberland Mens Fly ...
$120.00$59.79
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63% Off

Kenneth Cole Reaction Mens Casino Chukka Boots - Dark Gray - Size105Kenneth Cole Reaction ...
$110.00$40.19
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78% Off

Joseph Abboud Thomas Mens Chukka Boot - Chocolate Suede - Size 12Joseph Abboud Thomas ...
$125.00$26.99
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83% Off

Joseph Abboud Lucca Mens Chukka Boots - Brown - Size 95Joseph Abboud Lucca ...
$187.99$31.29
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82% Off

Adolfo Mens Broderick Chukka Boots - Brown - Size 95Adolfo Mens Broderick ...
$118.00$21.59
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73% Off

Adolfo Mens Charles Faux-Suede Chukka Boots - Gray - Size 85Adolfo Mens Charles ...
$122.99$33.69
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72% Off

Adolfo Mens Colin Chukka Boots - Navy - Size105Adolfo Mens Colin ...
$122.99$33.99
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76% Off

Akademiks Mens Mid-Top Chukka Boat Shoes - Grey - Size105Akademiks Mens Mid-Top ...
$74.99$17.89
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75% Off

Akademiks Mens Nubuck Mid-Top Chukka Boots - Black - Size 9Akademiks Mens Nubuck ...
$112.99$27.69
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69% Off

Vance Mens Manson Chukka Boots - Gray - Size10Vance Mens Manson ...
$89.99$27.69
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