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Men's Size 8.5 Medium Size Comfort Products

638 items found

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Cole Haan - Judson Grand Chelsea Boots. Color Black Waterproof/Black/Black. $259.95.

Black Cole Haan Judson Grand Chelsea Boots

Black Cole Haan Judson Grand Chelsea Boots

+2

Brand Name: Cole Haan
Product Name: Judson Grand Chelsea Boots
Gender: Men's
Color: Black Waterproof/Black/Black
Price: $259.95
Rating

Dunham - Windsor Waterproof. Color Brown Waterproof Milled Leather. $169.95. 4.4 out of 5 stars

Brown Dunham Windsor Waterproof

Brown Dunham Windsor Waterproof

Brand Name: Dunham
Product Name: Windsor Waterproof
Gender: Men's
Color: Brown Waterproof Milled Leather
Price: $169.95
Rating: 4Rated 4 stars out of 5(370)

Stacy Adams - Brumley Moc Toe Lace-Up Boots. Color Brown Multi. On sale for $144.00. MSRP $160.00. 10% off.

Black Stacy Adams Brumley Moc Toe Lace-Up Boots

Black Stacy Adams Brumley Moc Toe Lace-Up Boots

+2 colors/patterns

Brand Name: Stacy Adams
Product Name: Brumley Moc Toe Lace-Up Boots
Gender: Men's
Color: Brown Multi
Price: $144MSRP: $16010% OFF
Rating

Eastland 1955 Edition - Chimney Pond. Color Black. On sale for $87.00. MSRP $145.00. 40% off. 5.0 out of 5 stars

Black Eastland 1955 Edition Chimney Pond

Black Eastland 1955 Edition Chimney Pond

+2

Brand Name: Eastland 1955 Edition
Product Name: Chimney Pond
Gender: Men's
Color: Black
Price: $87MSRP: $14540% OFF
Rating: 5Rated 5 stars out of 5(2)

Born - Ryker Oxford. Color Black. On sale for $97.50. MSRP $130.00. 25% off. 1.5 out of 5 stars

Black Born Ryker Oxford

Black Born Ryker Oxford

Brand Name: Born
Product Name: Ryker Oxford
Gender: Men's
Color: Black
Price: $97.50MSRP: $13025% OFF
Rating: 2Rated 2 stars out of 5(2)

Mephisto - Gerome. Color Light Grey. Low Stock. On sale for $350.10. MSRP $389.00. 10% off.

Low Stock

Gray Mephisto Gerome

Gray Mephisto Gerome

+2 colors/patterns

Brand Name: Mephisto
Product Name: Gerome
Gender: Men's
Color: Light Grey
Price: $350.10MSRP: $38910% OFF
Rating

Tommy Hilfiger - Semaj. Color Medium Brown. Low Stock. On sale for $79.57. MSRP $109.00. 27% off. 2.0 out of 5 stars

Low Stock

Brown Tommy Hilfiger Semaj

Brown Tommy Hilfiger Semaj

+2

Brand Name: Tommy Hilfiger
Product Name: Semaj
Gender: Men's
Color: Medium Brown
Price: $79.57MSRP: $10927% OFF
Rating: 2Rated 2 stars out of 5(1)

Clarks - Aldwin Step. Color Black Leather. $110.00. 3.0 out of 5 stars

Black Clarks Aldwin Step

Black Clarks Aldwin Step

Brand Name: Clarks
Product Name: Aldwin Step
Gender: Men's
Color: Black Leather
Price: $110
Rating: 3Rated 3 stars out of 5(4)

SKECHERS - Max Cushioning Endeavour. Color White/Multi. On sale for $62.54. MSRP $80.00. 22% off. 3.8 out of 5 stars

Multi SKECHERS Max Cushioning Endeavour

Multi SKECHERS Max Cushioning Endeavour

Brand Name: SKECHERS
Product Name: Max Cushioning Endeavour
Gender: Men's
Color: White/Multi
Price: $62.54MSRP: $8022% OFF
Rating: 4Rated 4 stars out of 5(17)

Deer Stags - Albany. Color Dark Luggage. On sale for $54.99. MSRP $90.00. 39% off. 4.0 out of 5 stars

Brown Deer Stags Albany

Brown Deer Stags Albany

+2

Brand Name: Deer Stags
Product Name: Albany
Gender: Men's
Color: Dark Luggage
Price: $54.99MSRP: $9039% OFF
Rating: 4Rated 4 stars out of 5(3)

PIKOLINOS - Getafe M2B. Color Cuero. Low Stock. $210.00.

Low Stock

Tan PIKOLINOS Getafe M2B

Tan PIKOLINOS Getafe M2B

+1

Brand Name: PIKOLINOS
Product Name: Getafe M2B
Gender: Men's
Color: Cuero
Price: $210
Rating

Clarks - Burchill Derby. Color Beeswax Leather. On sale for $79.99. MSRP $100.00. 20% off. 3.4 out of 5 stars

Brown Clarks Burchill Derby

Brown Clarks Burchill Derby

Brand Name: Clarks
Product Name: Burchill Derby
Gender: Men's
Color: Beeswax Leather
Price: $79.99MSRP: $10020% OFF
Rating: 3Rated 3 stars out of 5(7)

Mephisto - Will. Color Black. $299.00.

Black Mephisto Will

Black Mephisto Will

Brand Name: Mephisto
Product Name: Will
Gender: Men's
Color: Black
Price: $299
Rating

. Timberland PRO - Nashoba Composite Safety Toe. Color Turkish Coffee-2024 NEW. On sale for $164.95. MSRP $180.00. 8% off. 3.8 out of 5 stars

Brown Timberland PRO Nashoba Composite Safety Toe

Brown Timberland PRO Nashoba Composite Safety Toe

+2

Brand Name: Timberland PRO
Product Name: Nashoba Composite Safety Toe
Gender: Unisex
Color: Turkish Coffee-2024 NEW
Price: $164.95MSRP: $1808% OFF
Rating: 4Rated 4 stars out of 5(87)

Born - Cambridge. Color Dark Brown (Braken). Low Stock. On sale for $121.50. MSRP $135.00. 10% off.

Low Stock

Brown Born Cambridge

Brown Born Cambridge

Brand Name: Born
Product Name: Cambridge
Gender: Men's
Color: Dark Brown (Braken)
Price: $121.50MSRP: $13510% OFF
Rating

New Balance - Composite Toe Cremorne Fresh Foam. Color Chocolate. On sale for $125.99. MSRP $159.99. 21% off. 3.5 out of 5 stars

Brown New Balance Composite Toe Cremorne Fresh Foam

Brown New Balance Composite Toe Cremorne Fresh Foam

+2

Brand Name: New Balance
Product Name: Composite Toe Cremorne Fresh Foam
Gender: Men's
Color: Chocolate
Price: $125.99MSRP: $159.9921% OFF
Rating: 3Rated 3 stars out of 5(81)

Bruno Magli - Bresso. Color Brown. Low Stock. $298.00.

Low Stock

Brown Bruno Magli Bresso

Brown Bruno Magli Bresso

Brand Name: Bruno Magli
Product Name: Bresso
Gender: Men's
Color: Brown
Price: $298
Rating

Deer Stags - Bangor. Color Black/Black. On sale for $54.00. MSRP $90.00. 40% off. 3.9 out of 5 stars

Black Deer Stags Bangor

Black Deer Stags Bangor

Brand Name: Deer Stags
Product Name: Bangor
Gender: Men's
Color: Black/Black
Price: $54MSRP: $9040% OFF
Rating: 4Rated 4 stars out of 5(14)

Bruno Magli - Matteo. Color Taupe. On sale for $208.60. MSRP $298.00. 30% off.

Taupe Bruno Magli Matteo

Taupe Bruno Magli Matteo

+2

Brand Name: Bruno Magli
Product Name: Matteo
Gender: Men's
Color: Taupe
Price: $208.60MSRP: $29830% OFF
Rating

Rockport - Tristen Step Activated Slip-On. Color Black Leather. On sale for $107.82. MSRP $119.95. 10% off. 3.0 out of 5 stars

Black Rockport Tristen Step Activated Slip-On

Black Rockport Tristen Step Activated Slip-On

Brand Name: Rockport
Product Name: Tristen Step Activated Slip-On
Gender: Men's
Color: Black Leather
Price: $107.82MSRP: $119.9510% OFF
Rating: 3Rated 3 stars out of 5(2)

SKECHERS - Arch Fit 2.0 Upperhand. Color Black/Gray. On sale for $76.84. MSRP $85.00. 10% off. 4.1 out of 5 stars

Black SKECHERS Arch Fit 2.0 Upperhand

Black SKECHERS Arch Fit 2.0 Upperhand

Brand Name: SKECHERS
Product Name: Arch Fit 2.0 Upperhand
Gender: Men's
Color: Black/Gray
Price: $76.84MSRP: $8510% OFF
Rating: 4Rated 4 stars out of 5(91)

Salomon - Aero Blaze 3. Color Black/Black/Ftw Silver. $160.00. 4.0 out of 5 stars

Black Salomon Aero Blaze 3

Black Salomon Aero Blaze 3

+2

Brand Name: Salomon
Product Name: Aero Blaze 3
Gender: Men's
Color: Black/Black/Ftw Silver
Price: $160
Rating: 4Rated 4 stars out of 5(1)

KEEN - Hightrail EXP Waterproof Hiking Shoes. Color Black/Magnet. $154.95. 4.3 out of 5 stars

Silver KEEN Hightrail EXP Waterproof Hiking Shoes

Silver KEEN Hightrail EXP Waterproof Hiking Shoes

Brand Name: KEEN
Product Name: Hightrail EXP Waterproof Hiking Shoes
Gender: Men's
Color: Black/Magnet
Price: $154.95
Rating: 4Rated 4 stars out of 5(3)

Eastland 1955 Edition - DANTE. Color Natural. On sale for $52.50. MSRP $75.00. 30% off. 4.0 out of 5 stars

Gray Eastland 1955 Edition DANTE

Gray Eastland 1955 Edition DANTE

Brand Name: Eastland 1955 Edition
Product Name: DANTE
Gender: Men's
Color: Natural
Price: $52.50MSRP: $7530% OFF
Rating: 4Rated 4 stars out of 5(2)

Eastland 1955 Edition - Bristol. Color Black. On sale for $102.64. MSRP $180.00. 43% off. 3.0 out of 5 stars

Black Eastland 1955 Edition Bristol

Black Eastland 1955 Edition Bristol

+2

Brand Name: Eastland 1955 Edition
Product Name: Bristol
Gender: Men's
Color: Black
Price: $102.64MSRP: $18043% OFF
Rating: 3Rated 3 stars out of 5(2)

Hoka - Cielo X1 2.0. Color Skyward Blue/Cielo Blue. $275.00. 3.5 out of 5 stars

Blue Hoka Cielo X1 2.0

Blue Hoka Cielo X1 2.0

+2

Brand Name: Hoka
Product Name: Cielo X1 2.0
Gender: Unisex
Color: Skyward Blue/Cielo Blue
Price: $275
Rating: 4Rated 4 stars out of 5(4)

Johnston & Murphy - XC4 TR3-Luxe Hybrid. Color Navy. Low Stock. $188.95. 4.1 out of 5 stars

Low Stock

Navy Johnston & Murphy XC4 TR3-Luxe Hybrid

Navy Johnston & Murphy XC4 TR3-Luxe Hybrid

+2

Brand Name: Johnston & Murphy
Product Name: XC4 TR3-Luxe Hybrid
Gender: Men's
Color: Navy
Price: $188.95
Rating: 4Rated 4 stars out of 5(57)

Samuel Hubbard - Olema Sport. Color Gray Nubuck. On sale for $136.50. MSRP $195.00. 30% off. 2.3 out of 5 stars

Gray Samuel Hubbard Olema Sport

Gray Samuel Hubbard Olema Sport

+2

Brand Name: Samuel Hubbard
Product Name: Olema Sport
Gender: Men's
Color: Gray Nubuck
Price: $136.50MSRP: $19530% OFF
Rating: 2Rated 2 stars out of 5(3)

Tommy Hilfiger - Sagent. Color Medium Brown. On sale for $79.57. MSRP $109.00. 27% off.

Brown Tommy Hilfiger Sagent

Brown Tommy Hilfiger Sagent

+2

Brand Name: Tommy Hilfiger
Product Name: Sagent
Gender: Men's
Color: Medium Brown
Price: $79.57MSRP: $10927% OFF
Rating

Bruno Magli - Maioco Penny. Color Cognac. $395.00.

Tan Bruno Magli Maioco Penny

Tan Bruno Magli Maioco Penny

+2

Brand Name: Bruno Magli
Product Name: Maioco Penny
Gender: Men's
Color: Cognac
Price: $395
Rating

Mephisto - Adrien. Color Dark Brown. $369.00. 5.0 out of 5 stars

Brown Mephisto Adrien

Brown Mephisto Adrien

+2

Brand Name: Mephisto
Product Name: Adrien
Gender: Men's
Color: Dark Brown
Price: $369
Rating: 5Rated 5 stars out of 5(1)

Allen Edmonds - Oliver Slip-on Stretch-lace Sneaker. Color Navy. Low Stock. On sale for $350.00. MSRP $375.00. 7% off. 5.0 out of 5 stars

Low Stock

Navy Allen Edmonds Oliver Slip-on Stretch-lace Sneaker

Navy Allen Edmonds Oliver Slip-on Stretch-lace Sneaker

Brand Name: Allen Edmonds
Product Name: Oliver Slip-on Stretch-lace Sneaker
Gender: Men's
Color: Navy
Price: $350MSRP: $3757% OFF
Rating: 5Rated 5 stars out of 5(3)

To Boot New York - Clapton. Color Brown. Low Stock. $450.00.

Low Stock

Brown To Boot New York Clapton

Brown To Boot New York Clapton

+2

Brand Name: To Boot New York
Product Name: Clapton
Gender: Men's
Color: Brown
Price: $450
Rating

Mephisto - Will Perf. Color Sand Bucklux. Low Stock. $289.00.

Low Stock

Brown Mephisto Will Perf

Brown Mephisto Will Perf

+2

Brand Name: Mephisto
Product Name: Will Perf
Gender: Men's
Color: Sand Bucklux
Price: $289
Rating

TYR - Valkyrie Elite Carbon. Color White/Black. $250.00.

Black TYR Valkyrie Elite Carbon

Black TYR Valkyrie Elite Carbon

Brand Name: TYR
Product Name: Valkyrie Elite Carbon
Gender: Unisex
Color: White/Black
Price: $250
Rating

Carhartt - Greenfield SD Nano Toe Work Sneakers. Color Brown/Black. $109.99. 2.9 out of 5 stars

Brown Carhartt Greenfield SD Nano Toe Work Sneakers

Brown Carhartt Greenfield SD Nano Toe Work Sneakers

+3

Brand Name: Carhartt
Product Name: Greenfield SD Nano Toe Work Sneakers
Gender: Men's
Color: Brown/Black
Price: $109.99
Rating: 3Rated 3 stars out of 5(11)

Allen Edmonds - Park Boot. Color Chili. Low Stock. On sale for $385.00. MSRP $550.00. 30% off. 3.9 out of 5 stars

Low Stock

Brown Allen Edmonds Park Boot

Brown Allen Edmonds Park Boot

+2

Brand Name: Allen Edmonds
Product Name: Park Boot
Gender: Men's
Color: Chili
Price: $385MSRP: $55030% OFF
Rating: 4Rated 4 stars out of 5(15)

Allen Edmonds - Elliot Lace-Up Shoes. Color Black Leather. Low Stock. $325.00.

Low Stock

Black Allen Edmonds Elliot Lace-Up Shoes

Black Allen Edmonds Elliot Lace-Up Shoes

Brand Name: Allen Edmonds
Product Name: Elliot Lace-Up Shoes
Gender: Men's
Color: Black Leather
Price: $325
Rating

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