Mens Chelsea Boots

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5% Off

Original Penguin HUGH CHELSEA BOOTOriginal Penguin HUGH ...
$190.00$180.00
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5% Off

Original Penguin HUGH CHELSEA BOOTOriginal Penguin HUGH ...
$190.00$180.00
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61% Off

Tampa Chelsea Boots - Slip-Ons For MenTampa Chelsea Boots - ...
$110.00$43.00
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61% Off

Tampa Chelsea Boots - Slip-Ons For MenTampa Chelsea Boots - ...
$110.00$43.00
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59% Off

Deadbolt Chelsea Boots - Leather For MenDeadbolt Chelsea Boots -...
$120.00$49.00
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59% Off

Deadbolt Chelsea Boots - Leather For MenDeadbolt Chelsea Boots -...
$120.00$49.00
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60% Off

Parson Chelsea Boots - Vegan Leather For MenParson Chelsea Boots - ...
$124.00$49.99
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60% Off

Parson Chelsea Boots - Vegan Leather For MenParson Chelsea Boots - ...
$124.00$49.99
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59% Off

All-Terrain Chelsea Work Boots - Composite Safety Toe, Leather For MenAll-Terrain Chelsea ...
$122.00$49.99
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61% Off

World Vue Chelsea Boots - Waterproof, Slip-Ons For MenWorld Vue Chelsea Boots ...
$150.00$59.00
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61% Off

World Vue Chelsea Boots - Waterproof, Slip-Ons For MenWorld Vue Chelsea Boots ...
$150.00$59.00
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63% Off

Tyler 31 Chelsea Boots - Slip-Ons For MenTyler 31 Chelsea Boots -...
$160.00$59.00
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36% Off

Camden Chelsea Boots - Nubuck For MenCamden Chelsea Boots - ...
$110.00$69.99
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36% Off

Camden Chelsea Boots - Nubuck For MenCamden Chelsea Boots - ...
$110.00$69.99
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59% Off

Neuman Chelsea Boots For MenNeuman Chelsea Boots For Men
$195.00$79.00
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50% Off

Tyler 31 Chelsea Boots - Slip-Ons For MenTyler 31 Chelsea Boots -...
$160.00$79.99
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49% Off

Stanley 03 Chelsea Boots For MenStanley 03 Chelsea ...
$175.00$89.99
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49% Off

Stanley 03 Chelsea Boots For MenStanley 03 Chelsea ...
$175.00$89.99
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49% Off

Stanley 03 Chelsea Boots For MenStanley 03 Chelsea ...
$175.00$89.99
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29% Off

Gold Cup Exeter Chelsea Boots - Suede For MenGold Cup Exeter Chelsea ...
$140.00$99.99
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62% Off

Made in Italy Tall Chelsea Boots - Leather For MenMade in Italy Tall ...
$525.00$199.99
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33% Off

Chelsea Rancher Boots - Leather, Factory 2nds For MenChelsea Rancher Boots - ...
$300.00$199.99
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33% Off

Chelsea Rancher Boots - Leather, Factory 2nds For MenChelsea Rancher Boots - ...
$300.00$199.99
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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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44% Off

Perry Ellis Mens Deville Chelsea Boots Black - Size 80 MPerry Ellis Mens ...
$89.99$49.99
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14% Off

Bearpaw Mens Marcus Chelsea Boots Black - Size 90 MBearpaw Mens Marcus ...
$69.99$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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Deer Stags Mens Rockland Memory Foam Chelsea Boots Black/Black - Size 85 MDeer Stags Mens ...
$74.99
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Deer Stags Mens Rockland Memory Foam Chelsea Boots Redwood/Dark Brown - Size 85 MDeer Stags Mens ...
$74.99
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Deer Stags Mens Argos Memory Foam Cap Toe Chelsea Boots Black - Size 80 MDeer Stags Mens Argos ...
$74.99
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Deer Stags Mens Argos Memory Foam Cap Toe Chelsea Boots Tan/Blue - Size 80 MDeer Stags Mens Argos ...
$74.99
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Deer Stags Mens Tribeca Chelsea Boots Luggage Leather - Size 85 MDeer Stags Mens Tribeca ...
$79.99
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44% Off

Dockers Mens Langford Chelsea Boots Brown - Size 75 MDockers Mens Langford ...
$89.99$50.00
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Dockers Mens Ashford Chelsea Boots Black Leather - Size 70 MDockers Mens Ashford ...
$89.99
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Dockers Mens Ashford Chelsea Boots Whiskey Leather - Size 70 MDockers Mens Ashford ...
$89.99
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Eastland Mens Daily Double Medium/Wide Chelsea Boots Black Leather - Size 70 MEastland Mens Daily ...
$114.99
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Florsheim Mens Uptown Medium/X-Wide Plain Toe Chelsea Boots Black Suede - Size 115 DFlorsheim Mens Uptown ...
$119.99
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Florsheim Mens Uptown Medium/X-Wide Plain Toe Chelsea Boots Cognac Leather - Size 130 DFlorsheim Mens Uptown ...
$119.99
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Florsheim Mens Uptown Medium/X-Wide Plain Toe Chelsea Boots Brown Suede - Size 105 3EFlorsheim Mens Uptown ...
$119.99
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20% Off

Nunn Bush Mens Otis Medium/Wide Plain Toe Chelsea Boots Black Tumbled - Size 70 MNunn Bush Mens Otis ...
$94.99$75.99
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20% Off

Nunn Bush Mens Otis Medium/Wide Plain Toe Chelsea Boots Brown Leather - Size 75 MNunn Bush Mens Otis ...
$94.99$75.99
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20% Off

Nunn Bush Mens Otis Medium/Wide Plain Toe Chelsea Boots Rust Leather - Size 80 MNunn Bush Mens Otis ...
$94.99$75.99
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Skechers Mens Blaine-Orsen Chelsea Boots Black - Size 65 MSkechers Mens Blaine-...
$89.99
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Skechers Mens Molton Gaveno Relaxed Fit Chelsea Boots Black - Size 75 MSkechers Mens Molton ...
$104.99
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Skechers Mens Molton Gaveno Relaxed Fit Chelsea Boots Brown - Size 80 MSkechers Mens Molton ...
$104.99
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Crevo Mens Denham Chelsea Boots Black Suede - Size 95 MCrevo Mens Denham ...
$89.99
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