Mens Chelsea Boots

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19% Off

Rockport Wynstin ChelseaRockport Wynstin Chelsea
$130.00$104.99
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19% Off

Rockport Wynstin ChelseaRockport Wynstin Chelsea
$130.00$104.99
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19% Off

Rockport Wynstin ChelseaRockport Wynstin Chelsea
$130.00$104.99
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35% Off

Rockport World Explorer ChelseaRockport World Explorer ...
$170.00$109.99
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35% Off

Rockport World Explorer ChelseaRockport World Explorer ...
$170.00$109.99
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27% Off

Outlet Urban Retreat ChelseaOutlet Urban Retreat Chelsea
$150.00$109.99
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27% Off

Outlet Urban Retreat ChelseaOutlet Urban Retreat Chelsea
$150.00$109.99
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25% Off

Outlet Total Motion PS ChelseaOutlet Total Motion PS ...
$160.00$119.97
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71% Off

Blundstone Canvas Chelsea Boots - Factory 2nds For Men and WomenBlundstone Canvas ...
$119.95$34.99
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71% Off

Blundstone Canvas Chelsea Boots - Factory 2nds For Men and WomenBlundstone Canvas ...
$119.95$34.99
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71% Off

Blundstone Canvas Chelsea Boots - Factory 2nds For Men and WomenBlundstone Canvas ...
$119.95$34.99
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71% Off

Blundstone Canvas Chelsea Boots - Factory 2nds For Men and WomenBlundstone Canvas ...
$119.95$34.99
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71% Off

Blundstone Canvas Chelsea Boots - Factory 2nds For Men and WomenBlundstone Canvas ...
$119.95$34.99
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71% Off

Blundstone Canvas Chelsea Boots - Factory 2nds For Men and WomenBlundstone Canvas ...
$119.95$34.99
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70% Off

Freemont Chelsea Boots - Leather For MenFreemont Chelsea Boots -...
$130.00$39.00
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70% Off

Freemont Chelsea Boots - Leather For MenFreemont Chelsea Boots -...
$130.00$39.00
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72% Off

Beck Rigby Chelsea Boots - Leather For MenBeck Rigby Chelsea ...
$140.00$39.00
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72% Off

Beck Rigby Chelsea Boots - Leather For MenBeck Rigby Chelsea ...
$140.00$39.00
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53% Off

Merrell Brevard Chelsea Boots - Nubuck For MenMerrell Brevard Chelsea ...
$150.00$69.99
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54% Off

Chelsea Dress Boots - Leather, Factory 2nds For MenChelsea Dress Boots - ...
$175.00$79.99
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54% Off

1312 Chelsea Boots - Leather, Factory 2nds For Men1312 Chelsea Boots - ...
$175.00$79.99
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54% Off

66 Chelsea Boots - Leather, Factory 2nds For Men66 Chelsea Boots - ...
$175.00$79.99
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58% Off

Super 550 Chelsea Boots - Leather, Factory 2nds For MenSuper 550 Chelsea Boots ...
$190.00$79.99
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58% Off

Super 550 Chelsea Boots - Leather, Factory 2nds For MenSuper 550 Chelsea Boots ...
$190.00$79.99
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58% Off

Super 550 Chelsea Boots - Leather, Factory 2nds For MenSuper 550 Chelsea Boots ...
$190.00$79.99
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29% Off

Structure Mens Fitz Brown Chelsea Boot, Size 11Structure Mens Fitz ...
$70.00$49.99
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50% Off

SM New York Mens Talent Chelsea Boot - Black, Size 8SM New York Mens Talent ...
$60.00$29.99
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Covington Mens Cicero 5 Chelsea Boot - Black, Size 10Covington Mens Cicero 5 ...
$60.00
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59% Off

COACH - Claremont Chelsea Dark Saddle Mens Pull-on BootsCOACH - Claremont ...
$295.00$119.99
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50% Off

John Varvatos - Fleetwood Chelsea Indigo Mens Pull-on BootsJohn Varvatos - ...
$698.00$349.99
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43% Off

Marc Jacobs - Classic Leather Chelsea Boot Black Mens BootsMarc Jacobs - Classic ...
$790.00$448.33
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62% Off

Columbia - Davenport Chelsea Waterproof Black/Dark Fog Mens Waterproof BootsColumbia - Davenport ...
$130.00$49.99
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50% Off

Frye - Riley Chelsea Dark Brown Waterproof Suede Mens Pull-on BootsFrye - Riley Chelsea ...
$258.00$129.00
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39% Off

Frye - Seth Chelsea Chestnut Oiled Suede Mens Pull-on BootsFrye - Seth Chelsea ...
$228.00$137.99
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50% Off

Frye - Sam Chelsea Cognac Smooth Antique Pull Up Mens Pull-on BootsFrye - Sam Chelsea ...
$298.00$149.00
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50% Off

Frye - Jones Chelsea Tobacco Soft Italian Nubuck Mens BootsFrye - Jones Chelsea ...
$328.00$164.00
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40% Off

Frye - Arden Chelsea Brown Oiled Suede Mens Pull-on BootsFrye - Arden Chelsea ...
$278.00$167.99
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50% Off

Frye - Edwin Chelsea Slate Weatherproof Suede Mens Pull-on BootsFrye - Edwin Chelsea ...
$358.00$179.00
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50% Off

Frye - Austin Chelsea Black Washed Tumbled Full Grain Mens BootsFrye - Austin Chelsea ...
$378.00$189.99
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40% Off

Frye - Country Crepe Chelsea Cognac Deer Skin Leather Mens Pull-on BootsFrye - Country Crepe ...
$328.00$197.99
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40% Off

Frye - Jet Chelsea Black Smooth Veg Calf Mens BootsFrye - Jet Chelsea ...
$348.00$209.99
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40% Off

Frye - Stone Harness Chelsea Whiskey Smooth Pull-Up Mens Pull-on BootsFrye - Stone Harness ...
$358.00$214.99
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40% Off

Frye - Austin Chelsea Copper Oiled Suede Mens BootsFrye - Austin Chelsea ...
$378.00$227.99
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30% Off

Frye - Chris Chelsea Brown Oiled Suede Mens BootsFrye - Chris Chelsea ...
$328.00$229.99
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35% Off

Frye - Greyson Chelsea Black Deer Skin Leather Mens Pull-on BootsFrye - Greyson Chelsea ...
$428.00$277.99
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45% Off

Merrell - Brevard Chelsea Shetland Mens BootsMerrell - Brevard ...
$150.00$82.99
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40% Off

SOREL - Madson Chelsea Waterproof Curry/Tobacco Mens Waterproof BootsSOREL - Madson Chelsea ...
$160.00$95.99
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40% Off

Timberland - Carter Notch Plain Toe Chelsea Black Full Grain Mens Pull-on BootsTimberland - Carter ...
$150.00$89.99
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40% Off

Timberland - Carter Notch Plain Toe Chelsea Olive Full Grain Mens Pull-on BootsTimberland - Carter ...
$150.00$89.99
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35% Off

Timberland - Carter Notch Plain Toe Chelsea Dark Brown Full Grain Mens Pull-on BootsTimberland - Carter ...
$150.00$97.99
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30% Off

Timberland - Earthkeepersr Chestnut Ridge Chelsea Waterproof Brown Oiled Mens Pull-on BootsTimberland - ...
$150.00$104.99
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34% Off

Timberland - Britton Hill Chelsea Black Full Grain Mens BootsTimberland - Britton ...
$160.00$104.99
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20% Off

Timberland - Earthkeepersr Chestnut Ridge Chelsea Waterproof Black Smooth Mens Pull-on BootsTimberland - ...
$150.00$119.99
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33% Off

Wolverine - 1000 Mile Montague Chelsea Boot Brown Mens Pull-on BootsWolverine - 1000 Mile ...
$295.00$199.00
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50% Off

Sperry - Decoy Chelsea Waterproof Tan Mens BootsSperry - Decoy Chelsea ...
$120.00$59.99
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35% Off

Sperry - Dockyard Chelsea Tan Mens BootsSperry - Dockyard ...
$150.00$97.99
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55% Off

Alexander McQueen - Chelsea Boot Black Mens BootsAlexander McQueen - ...
$995.00$447.99
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50% Off

Ben Sherman - Gaston Chelsea Black Mens BootsBen Sherman - Gaston ...
$110.00$54.99
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35% Off

BOSS Hugo Boss - Deluxe Suede Chelsea Boot by HUGO Black Mens ShoesBOSS Hugo Boss - Deluxe ...
$445.00$289.99
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55% Off

BUGATCHI - Brescia Chelsea Boot Ardesia Mens BootsBUGATCHI - Brescia ...
$300.00$134.99
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40% Off

Cole Haan - Montgomery Zip Chelsea Black Mens BootsCole Haan - Montgomery ...
$180.00$108.68
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60% Off

Cole Haan - Hamilton Grand Chelsea Dark Brown Mens BootsCole Haan - Hamilton ...
$300.00$120.00
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40% Off

Cole Haan - Grantland Chelsea Water Proof Black Water Proof Mens BootsCole Haan - Grantland ...
$240.00$143.34
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43% Off

Dr Martens - Lyme Chelsea Boot Tan Grizzly Mens Pull-on BootsDr Martens - Lyme ...
$120.00$68.00
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39% Off

Dr Martens - Oakford Chelsea Boot Tan/Biscuit Grizzly/Hi Suede WP Mens Pull-on BootsDr Martens - Oakford ...
$115.00$70.45
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37% Off

Dr Martens - Lyme Chelsea Boot Black Slippery Wp Mens Pull-on BootsDr Martens - Lyme ...
$120.00$75.20
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35% Off

Dr Martens - Lyme Chelsea Boot Tan Slippery Wp Mens Pull-on BootsDr Martens - Lyme ...
$120.00$77.60
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30% Off

Dr Martens - Lyme Chelsea Boot Black Grizzly Mens Pull-on BootsDr Martens - Lyme ...
$120.00$84.00
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39% Off

Dr Martens - Wilde Low Chelsea Boot Black Temperley Mens Pull-on BootsDr Martens - Wilde Low ...
$145.00$88.45
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35% Off

Dr Martens - Hardy Chelsea Boot Black Temperley Mens BootsDr Martens - Hardy ...
$165.00$107.99
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36% Off

Dunham - Graham Chelsea Chocolate Mens Pull-on BootsDunham - Graham Chelsea ...
$165.00$105.86
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44% Off

ECCO - Knoxville Chelsea Boot Black Mens Dress Pull-on BootsECCO - Knoxville ...
$180.00$99.99
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50% Off

Johnston amp Murphy - Garner Chelsea Gore Boot Black Calfskin Mens Dress Pull-on BootsJohnston amp Murphy - ...
$178.95$89.99
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50% Off

Massimo Matteo - Chelsea Buckle Boot Black Mens Dress Pull-on BootsMassimo Matteo - ...
$189.00$94.99
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35% Off

Rockport - Urban Retreat Chelsea Bruin Mens BootsRockport - Urban ...
$150.00$97.96
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29% Off

Rockport - World Explorer Chelsea Black Mens BootsRockport - World ...
$149.95$107.11
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60% Off

Del Toro - Leather Zip Chelsea Boot Brown Mens BootsDel Toro - Leather Zip ...
$425.00$169.99
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55% Off

rag amp bone - Spencer Chelsea Antelope Suede Mens Bootsrag amp bone - Spencer ...
$495.00$224.99
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Dr Scholls Orig Collection Mens Credence Chelsea Boot Boots Black SuedeDr Scholls Orig ...
$125.00
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Dr Scholls Orig Collection Mens Credence Chelsea Boot Boots Tan SuedeDr Scholls Orig ...
$125.00
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33% Off

Perry Ellis Mens Deville Chelsea Boots Black - Size 80 MPerry Ellis Mens ...
$89.99$59.99
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7% Off

Bearpaw Mens Marcus Chelsea Boots Hickory - Size 80 MBearpaw Mens Marcus ...
$69.99$64.99
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Caterpillar Mens Brahm Chelsea Boots Black Leather - Size 70 MCaterpillar Mens Brahm ...
$124.99
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Caterpillar Mens Brahm Chelsea Boots Dark Grey Leather - Size 75 MCaterpillar Mens Brahm ...
$124.99
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30% Off

Deer Stags Mens Award Chelsea Boots Black Leather - Size 80 MDeer Stags Mens Award ...
$79.99$55.99
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30% Off

Deer Stags Mens Award Chelsea Boots Dark Luggage Leather - Size 80 MDeer Stags Mens Award ...
$79.99$55.99
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Deer Stags Mens Tribeca Chelsea Boots Black Leather - Size 85 MDeer Stags Mens Tribeca ...
$79.99
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Dockers Mens Ashford Chelsea Boots Black Leather - Size 80 MDockers Mens Ashford ...
$89.99
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Dockers Mens Ashford Chelsea Boots Whiskey Leather - Size 80 MDockers Mens Ashford ...
$89.99
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Dockers Mens Stanwell Chelsea Boots Dark Tan Leather - Size 85 MDockers Mens Stanwell ...
$89.99
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Dockers Mens Stanwell Chelsea Boots Black Leather - Size 90 MDockers Mens Stanwell ...
$89.99
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Dockers Mens Stanwell Chelsea Boots Chocolate Leather - Size 70 MDockers Mens Stanwell ...
$89.99
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Eastland Mens Daily Double Chelsea Boots Tan - Size 80 DEastland Mens Daily ...
$114.99
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Florsheim Mens Frisco Chelsea Boots Brown Leather - Size 110 DFlorsheim Mens Frisco ...
$124.99
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GBX Mens Packer Chelsea Boots Black Leather - Size 70 MGBX Mens Packer Chelsea ...
$84.99
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GBX Mens Packer Chelsea Boots Brown Leather - Size 70 MGBX Mens Packer Chelsea ...
$84.99
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GBX Mens Packer Chelsea Boots Stone Leather - Size 70 MGBX Mens Packer Chelsea ...
$84.99
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Giorgio Brutini Mens Aaron Chelsea Boots Black - Size 75 MGiorgio Brutini Mens ...
$64.99
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Giorgio Brutini Mens Cormac Medium/Wide Chelsea Boots Black - Size 70 WGiorgio Brutini Mens ...
$69.99
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Giorgio Brutini Mens Proof Chelsea Boots Black - Size 70 MGiorgio Brutini Mens ...
$69.99
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