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    Discount Size 8.5 Leather Mens Shoes

    1-36 of 594 results
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    New Balance 608v4 (Men's)
    New!
    Sale
    New Balance 608v4(Men's) -Black
    Sale
    New Balance 608v4(Men's) -White/Navy
    Sale
    New Balance 608v4(Men's) -White/Royal Blue
    Sale
    $69.95 - $74.95
    $75.00 up to 7% off
    Sperry Top-Sider Avenue Duck Boot (Men's)
    New!
    Sale
    Sperry Top-Sider Avenue Duck Boot(Men's) -Black/Amaretto Leather
    Sale
    Sperry Top-Sider Avenue Duck Boot(Men's) -Tan/Brown
    Sale
    $79.95
    $109.95 - $110.00 up to 27% off
    Rockport Margin Oxford (Men's)
    New!
    Sale
    Rockport Margin Oxford(Men's) -Black
    Sale
    Rockport Margin Oxford(Men's) -Chocolate
    Sale
    Rockport Margin Oxford(Men's) -Espresso Nubuck
    Sale
    $99.95
    $110.00 9% off
    Nunn Bush Bleeker Street (Men's)
    New!
    Sale
    Nunn Bush Bleeker Street(Men's) -Black Smooth Leather
    Sale
    Nunn Bush Bleeker Street(Men's) -Cognac Leather
    Sale
    $68.00
    $85.00 20% off
    Deer Stags Times (Men's)
    New!
    Sale
    Deer Stags Times(Men's) -Black Smooth
    Sale
    Deer Stags Times(Men's) -Brown Smooth
    Sale
    $49.99 - $64.95
    $64.95 - $65.00 up to 23% off
    Rockport Perth Loafer (Men's)
    New!
    Sale
    Rockport Perth Loafer(Men's) -Chocolate/Bark Nubuck
    Sale
    Rockport Perth Loafer(Men's) -Timber w/ Honey Sole
    Sale
    $109.95 - $124.95
    $125.00 up to 12% off
    G.H. Bass & Co. Larson Weejuns Penny Loafer (Men's)
    New!
    Sale
    G.H. Bass & Co. Larson Weejuns Penny Loafer(Men's) -Burgundy Pull Up Leather
    Sale
    $82.95 - $110.00
    $110.00 up to 25% off
    Bostonian Bolton (Men's)
    New!
    Sale
    Bostonian Bolton(Men's) -Black Smooth Leather
    Sale
    Bostonian Bolton(Men's) -Brown Smooth Leather
    Sale
    $79.95
    $90.00 11% off
    Nunn Bush Nelson 84525 Wing Tip Oxford (Men's)
    New!
    Sale
    Nunn Bush Nelson 84525 Wing Tip Oxford(Men's) -Black Leather
    Sale
    Nunn Bush Nelson 84525 Wing Tip Oxford(Men's) -Brown Leather
    Sale
    Nunn Bush Nelson 84525 Wing Tip Oxford(Men's) -Cognac Smooth Leather
    Sale
    $68.00
    $85.00 20% off
    Johnston & Murphy Aragon II Loafer (Men's)
    New!
    Sale
    Johnston & Murphy Aragon II Loafer(Men's) -Black Deer with Black Waxhide Trim
    Sale
    $99.95 - $134.95
    $134.95 - $135.00 up to 26% off
    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(Men's) -Green Leather
    Sale
    $59.99 - $239.95
    $130.00 - $240.00 up to 54% off
    Clarks Bushacre 2 Boot (Men's)
    New!
    Sale
    Clarks Bushacre 2 Boot(Men's) -Beeswax Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Black Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Black Suede
    Sale
    Clarks Bushacre 2 Boot(Men's) -Brown Suede
    Sale
    Clarks Bushacre 2 Boot(Men's) -Dark Brown Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Grey Leather
    Sale
    Clarks Bushacre 2 Boot(Men's) -Navy Leather
    Sale
    $84.95 - $99.95
    $100.00 up to 15% off
    Bostonian Ipswich Oxford (Men's)
    New!
    Sale
    Bostonian Ipswich Oxford(Men's) -Black Smooth Leather
    Sale
    Bostonian Ipswich Oxford(Men's) -Brown Smooth Leather
    Sale
    $79.95
    $90.00 11% off
    Skechers Relaxed Fit Glides Calculous Slip On (Men's)
    New!
    Sale
    Skechers Relaxed Fit Glides Calculous Slip On(Men's) -Black
    Sale
    Skechers Relaxed Fit Glides Calculous Slip On(Men's) -Dark Brown
    Sale
    $64.95 - $74.95
    $70.00 - $75.00 up to 13% off
    Ariat Rambler Square Toe Boot (Men's)
    New!
    Sale
    Ariat Rambler Square Toe Boot(Men's) -Brown Bomber Full Grain Leather
    Sale
    Ariat Rambler Square Toe Boot(Men's) -Wicker Distressed Leather
    Sale
    $149.95
    $159.95 6% off
    Clarks Niland Energy Slip-on (Men's)
    New!
    Sale
    Clarks Niland Energy Slip-on(Men's) -Black Tumbled
    Sale
    Clarks Niland Energy Slip-on(Men's) -Black Tumbled Leather
    Sale
    Clarks Niland Energy Slip-on(Men's) -Brown Tumbled
    Sale
    $84.95
    $90.00 6% off
    Skechers Work Relaxed Fit Workshire Steel Toe (Men's)
    New!
    Sale
    Skechers Work Relaxed Fit Workshire Steel Toe(Men's) -Dark Brown
    Sale
    $77.45 - $84.95
    $85.00 - $90.00 up to 14% off
    UGG Messner Boot (Men's)
    New!
    Sale
    UGG Messner Boot(Men's) -Black
    Sale
    UGG Messner Boot(Men's) -Stout
    Sale
    $157.95
    $210.00 25% off
    Clarks Tilden Cap Toe Oxford (Men's)
    New!
    Sale
    Clarks Tilden Cap Toe Oxford(Men's) -Black Leather
    Sale
    Clarks Tilden Cap Toe Oxford(Men's) -Brown Leather
    Sale
    $79.95
    $90.00 11% off
    Rockport World Tour Encounter (Men's)
    New!
    Sale
    Rockport World Tour Encounter(Men's) -Black Tumbled
    Sale
    Rockport World Tour Encounter(Men's) -Dark Brown Tumbled
    Sale
    $109.95
    $120.00 8% off
    Ariat Workhog Wide Square Toe (Men's)
    New!
    Sale
    Ariat Workhog Wide Square Toe(Men's) -Dark Earth/Brick Full Grain Leather
    Sale
    Ariat Workhog Wide Square Toe(Men's) -Mossy Oak Full Grain Leather
    Sale
    Ariat Workhog Wide Square Toe(Men's) -Rugged Bark Full Grain Leather
    Sale
    Ariat Workhog Wide Square Toe(Men's) -Toast Premium USA Full Grain Leather
    Sale
    $169.95
    $189.95 11% off
    Johnston & Murphy Atchison Plain Cap Toe (Men's)
    New!
    Sale
    Johnston & Murphy Atchison Plain Cap Toe(Men's) -Black Brushed Calfskin
    Sale
    Johnston & Murphy Atchison Plain Cap Toe(Men's) -Burgundy Brushed Calfskin
    Sale
    $99.95
    $135.00 26% off
    Skechers Relaxed Fit Segment The Search (Men's)
    New!
    Sale
    Skechers Relaxed Fit Segment The Search(Men's) -Brown
    Sale
    $64.95 - $74.95
    $80.00 up to 19% off
    Ariat Barstow Cowboy Boot (Men's)
    New!
    Sale
    Ariat Barstow Cowboy Boot(Men's) -Bite The Dust Brown Full Grain Leather
    Sale
    Ariat Barstow Cowboy Boot(Men's) -Branding Iron Rust/Desert Eclipse Leather
    Sale
    $219.95
    $239.95 - $259.95 up to 15% off
    Clarks Stratton Limit Boot (Men's)
    New!
    Sale
    Clarks Stratton Limit Boot(Men's) -Black Leather
    Sale
    Clarks Stratton Limit Boot(Men's) -Brown Leather
    Sale
    $119.95
    $135.00 11% off
    Johnston & Murphy Norvell Moc Lace-Up (Men's)
    New!
    Sale
    Johnston & Murphy Norvell Moc Lace-Up(Men's) -Black Full Grain
    Sale
    Johnston & Murphy Norvell Moc Lace-Up(Men's) -Dark Mahogany Full Grain
    Sale
    $99.99
    $135.00 26% off
    Ariat Heritage Western R Toe (Men's)
    New!
    Sale
    Ariat Heritage Western R Toe(Men's) -Black Deertan Full Grain Leather
    Sale
    Ariat Heritage Western R Toe(Men's) -Distressed Brown Full Grain Leather
    Sale
    $159.95
    $179.95 11% off
    Merrell Moab Rover Hiking Shoe (Men's)
    New!
    Sale
    Merrell Moab Rover Hiking Shoe(Men's) -Merrell Tan
    Sale
    $107.95 - $119.95
    $120.00 up to 10% off
    Rockport Charson Lace Up Ankle Boot (Men's)
    New!
    Sale
    Rockport Charson Lace Up Ankle Boot(Men's) -Black Leather
    Sale
    Rockport Charson Lace Up Ankle Boot(Men's) -Chocolate Leather
    Sale
    Rockport Charson Lace Up Ankle Boot(Men's) -Dark Brown Leather
    Sale
    $87.95
    $140.00 37% off
    Johnston & Murphy Ski-Moc (Men's)
    New!
    Sale
    Johnston & Murphy Ski-Moc(Men's) -Burgundy Brushed Calfskin
    Sale
    Johnston & Murphy Ski-Moc(Men's) -Black Brushed Calfskin
    Sale
    $148.95
    $175.00 15% off
    Ariat Workhog? Wide Square Steel Toe Boot (Men's)
    New!
    Sale
    Ariat Workhog? Wide Square Steel Toe Boot(Men's) -Dark Earth/Brick Full Grain Leather
    Sale
    Ariat Workhog? Wide Square Steel Toe Boot(Men's) -Rugged Bark Full Grain Leather
    Sale
    Ariat Workhog? Wide Square Steel Toe Boot(Men's) -Toast Premium USA Full Grain Leather
    Sale
    $179.95
    $199.95 10% off