Mens Boots

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54% Off

Rockport truStride Lace to Toe ChukkaRockport truStride Lace ...
$130.00$59.99
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53% Off

Rockport Premium Class ChukkaRockport Premium Class ...
$150.00$69.99
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53% Off

Rockport Premium Class ChukkaRockport Premium Class ...
$150.00$69.99
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53% Off

Rockport Premium Class ChukkaRockport Premium Class ...
$150.00$69.99
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38% Off

Rockport Classic Break ChukkaRockport Classic Break ...
$130.00$79.99
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38% Off

Rockport Classic Break ChukkaRockport Classic Break ...
$130.00$79.99
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40% Off

Rockport Total Motion Fusion ChukkaRockport Total Motion ...
$150.00$89.97
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44% Off

Rockport Jaxson Low Boot ChukkaRockport Jaxson Low ...
$160.00$89.99
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31% Off

Rockport Wynstin ChukkaRockport Wynstin Chukka
$130.00$89.99
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31% Off

Rockport Wynstin ChukkaRockport Wynstin Chukka
$130.00$89.99
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44% Off

Rockport Jaxson ChukkaRockport Jaxson Chukka
$160.00$89.99
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33% Off

Rockport Total Motion Fusion ChukkaRockport Total Motion ...
$150.00$99.97
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29% Off

Rockport Total Motion Fusion ChukkaRockport Total Motion ...
$140.00$99.97
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33% Off

Rockport Total Motion Fusion ChukkaRockport Total Motion ...
$150.00$99.97
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20% Off

Rockport Tough Bucks ChukkaRockport Tough Bucks Chukka
$125.00$99.99
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20% Off

Rockport Tough Bucks ChukkaRockport Tough Bucks Chukka
$125.00$99.99
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20% Off

Rockport Tough Bucks ChukkaRockport Tough Bucks Chukka
$125.00$99.99
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17% Off

Rockport Essential Details II ChukkaRockport Essential ...
$120.00$99.99
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13% Off

Rockport Rydley ChukkaRockport Rydley Chukka
$115.00$99.99
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13% Off

Rockport Rydley ChukkaRockport Rydley Chukka
$115.00$99.99
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13% Off

Rockport Rydley ChukkaRockport Rydley Chukka
$115.00$99.99
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23% Off

Rockport Style Purpose Perf ChukkaRockport Style Purpose ...
$130.00$99.99
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23% Off

Rockport Style Purpose Perf ChukkaRockport Style Purpose ...
$130.00$99.99
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26% Off

Rockport Classic Break ChukkaRockport Classic Break ...
$135.00$99.99
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9% Off

Rockport Trail Technique Waterproof ChukkaRockport Trail ...
$110.00$99.99
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23% Off

Rockport Classic Break ChukkaRockport Classic Break ...
$130.00$99.99
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23% Off

Rockport Classic Break ChukkaRockport Classic Break ...
$130.00$99.99
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9% Off

Rockport Trail Technique Waterproof ChukkaRockport Trail ...
$110.00$99.99
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12% Off

Rockport Tough Bucks ChukkaRockport Tough Bucks Chukka
$125.00$109.99
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15% Off

Rockport Classic Break Low Boot ChukkaRockport Classic Break ...
$130.00$109.99
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12% Off

Rockport Tough Bucks ChukkaRockport Tough Bucks Chukka
$125.00$109.99
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12% Off

Rockport Tough Bucks ChukkaRockport Tough Bucks Chukka
$125.00$109.99
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31% Off

Rockport Jaxson ChukkaRockport Jaxson Chukka
$160.00$109.99
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20% Off

Rockport Ledge Hill 2 ChukkaRockport Ledge Hill 2 Chukka
$150.00$119.99
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Rockport Essential Details II ChukkaRockport Essential ...
$120.00
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24% Off

Rockport DresSports Modern Waterproof ChukkaRockport DresSports ...
$170.00$129.99
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13% Off

Rockport Total Motion Fusion ChukkaRockport Total Motion ...
$150.00$129.99
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Rockport Ledge Hill 2 ChukkaRockport Ledge Hill 2 Chukka
$150.00
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Rockport Ledge Hill 2 ChukkaRockport Ledge Hill 2 Chukka
$150.00
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Rockport Ledge Hill 2 ChukkaRockport Ledge Hill 2 Chukka
$150.00
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27% Off

Outlet Sharp  Ready Charson ChukkaOutlet Sharp Ready ...
$110.00$79.99
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27% Off

Outlet Sharp  Ready Charson ChukkaOutlet Sharp Ready ...
$110.00$79.99
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43% Off

Outlet Sharp  Ready Charson ChukkaOutlet Sharp Ready ...
$140.00$79.99
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33% Off

Outlet Ledge Hill 2 Lace Up ChukkaOutlet Ledge Hill 2 ...
$150.00$99.99
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33% Off

Outlet Ledge Hill 2 Lace Up ChukkaOutlet Ledge Hill 2 ...
$150.00$99.99
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Outlet Urban Retreat Chukka BootOutlet Urban Retreat ...
$140.00
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Outlet Ledge Hill 2 Lace Up ChukkaOutlet Ledge Hill 2 ...
$150.00
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Outlet Ledge Hill 2 Lace Up ChukkaOutlet Ledge Hill 2 ...
$150.00
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Outlet Ledge Hill 2 Lace Up ChukkaOutlet Ledge Hill 2 ...
$150.00
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Outlet Ledge Hill 2 Lace Up ChukkaOutlet Ledge Hill 2 ...
$150.00
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76% Off

Florsheim Doon Chukka Boots - Leather For MenFlorsheim Doon Chukka ...
$120.00$29.00
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65% Off

Hush Puppies Gage Parkview Chukka Boots - Leather For MenHush Puppies Gage ...
$109.99$39.00
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69% Off

Chaco Jaeger Chukka Boots - Leather For MenChaco Jaeger Chukka ...
$140.00$43.00
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66% Off

Merrell Bask Sol Mid Chukka Boots - Leather For MenMerrell Bask Sol Mid ...
$125.00$43.00
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68% Off

Rockit Chukka Boots - Leather For MenRockit Chukka Boots - ...
$135.00$43.00
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80% Off

Frye Gates Chukka Boots - Leather For MenFrye Gates Chukka Boots ...
$248.00$49.00
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67% Off

Merrell Brevard Leather Chukka Boots For MenMerrell Brevard Leather ...
$150.00$49.00
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38% Off

Simple Barney-91 Chukka Boots - Leather For MenSimple Barney-91 Chukka ...
$79.99$49.99
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38% Off

Simple Barney-91 Chukka Boots - Leather For MenSimple Barney-91 Chukka ...
$79.99$49.99
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50% Off

Merrell Freewheel Mesh Chukka Boots For MenMerrell Freewheel Mesh ...
$100.00$49.99
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60% Off

Thompson Chukka Boots - Vegan Leather For MenThompson Chukka Boots - ...
$124.00$49.99
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60% Off

Thompson Chukka Boots - Vegan Leather For MenThompson Chukka Boots - ...
$124.00$49.99
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60% Off

Thompson Chukka Boots - Vegan Leather For MenThompson Chukka Boots - ...
$124.00$49.99
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52% Off

Johnston and Murphy Wallace Chukka Boots - Suede For MenJohnston and Murphy ...
$125.00$59.99
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52% Off

Johnston and Murphy Wallace Chukka Boots - Suede For MenJohnston and Murphy ...
$125.00$59.99
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52% Off

Johnston and Murphy Wallace Chukka Boots - Suede For MenJohnston and Murphy ...
$125.00$59.99
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52% Off

Johnston and Murphy Wallace Chukka Boots - Suede For MenJohnston and Murphy ...
$125.00$59.99
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50% Off

Mens IZOD Cally Chukka Boots 12 M, Brown BridgeMens IZOD Cally Chukka ...
$69.99$34.99
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43% Off

Mens IZOD Incent Chukka Boots 13 M, Dark NaturalMens IZOD Incent Chukka ...
$69.99$39.99
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9% Off

Mens Clarks Vargo Mid Chukka Boots 13 M, Dark BrownMens Clarks Vargo Mid ...
$109.99$99.99
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Mens ClarksR Bushacre 2 Chukka Ankle Boots 11 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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Mens Eastland Seneca Chukka Boots - Tan 12 W, TanMens Eastland Seneca ...
$110.00
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Mens Eastland Seneca Chukka Boots - Brown 15 W, BrownMens Eastland Seneca ...
$110.00
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Mens Eastland Seneca Chukka Boots 13 D, Dark BrownMens Eastland Seneca ...
$110.00
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20% Off

Mens Florsheim Fenway Chukka Boots 95 D, Brown ChestnutMens Florsheim Fenway ...
$124.99$99.99
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Mens Florsheim Comfortech Edge Chukka Boots 95 M, Navy NubuckMens Florsheim ...
$110.00
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Mens Florsheim Union Plain Toe Chukka Boots 95 D, Black Crazy HorseMens Florsheim Union ...
$110.00
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Mens Florsheim Midtown Waterproof Chukka Boots 9 EEE, BlackMens Florsheim Midtown ...
$125.00
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Mens Florsheim Blaze Plain Toe Chukka Boots 95 D, CognacMens Florsheim Blaze ...
$130.00
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40% Off

Mens London Fog Broadstreet Chukkas 105 M, GreyMens London Fog ...
$49.99$29.99
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13% Off

Mens Nunn Bush Galloway Chukka Boots 12 W, NavyMens Nunn Bush Galloway ...
$80.00$70.00
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16% Off

Mens Nunn Bush Ozark Chukka Boots 95 M, TanMens Nunn Bush Ozark ...
$94.99$79.99
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11% Off

Mens Nunn Bush Lancaster Chukka Boots 12 W, CamelMens Nunn Bush ...
$90.00$80.00
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11% Off

Mens Nunn Bush Savage Chukka Boots 95 W, BrownMens Nunn Bush Savage ...
$95.00$85.00
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29% Off

Mens Skechers Ryler Mobert Chukka Boots 95 M, BlackMens Skechers Ryler ...
$69.99$49.99
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Mens Skechers Droven-Evado Chukkas 95 D, BeigeMens Skechers Droven-...
$74.99
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Mens Spring Step Men Mathias Chukka Boots - Black 47, BlackMens Spring Step Men ...
$99.99
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Mens Spring Step Mathias Chukka Boots - Brown 47, BrownMens Spring Step ...
$99.99
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12% Off

Mens Stacy Adams Buckley Chukka Boots 95 M, Yellow SuedeMens Stacy Adams ...
$85.00$75.00
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19% Off

Mens Stacy Adams Ashby Chukka Boots 95 M, CognacMens Stacy Adams Ashby ...
$104.99$84.99
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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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63% Off

Mens BZees by Naturalizer Ignite Chukkas 13 M, BrownMens BZees by ...
$79.99$29.99
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Mens Mark Nason Los Angeles Weldon Chukka Boots 9 M, NavyMens Mark Nason Los ...
$99.99
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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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