Winter Wins
Performance picks built for champions—on & off the mountain.
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Size 8.5 Medium Size Stacked Heel Shoes

149 items found

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Johnston & Murphy - Connelly Plain Toe Boots. Color Tan Full Grain. On sale for $149.99. MSRP $219.00. 32% off. 4.2 out of 5 stars

Tan Johnston & Murphy Connelly Plain Toe Boots

Tan Johnston & Murphy Connelly Plain Toe Boots

Brand Name: Johnston & Murphy
Product Name: Connelly Plain Toe Boots
Gender: Men's
Color: Tan Full Grain
Price: $149.99MSRP: $21932% OFF
Rating: 4Rated 4 stars out of 5(60)

Stacy Adams - Valet Velour Slip-On Loafer. Color Black. On sale for $79.90. MSRP $105.00. 24% off. 4.5 out of 5 stars

Black Stacy Adams Valet Velour Slip-On Loafer

Black Stacy Adams Valet Velour Slip-On Loafer

+2

Brand Name: Stacy Adams
Product Name: Valet Velour Slip-On Loafer
Gender: Men's
Color: Black
Price: $79.90MSRP: $10524% OFF
Rating: 5Rated 5 stars out of 5(113)

Ariat - Hybrid Grit Western Boots. Color Earth/Alamo Brown. $179.95. 4.5 out of 5 stars

Brown Ariat Hybrid Grit Western Boots

Brown Ariat Hybrid Grit Western Boots

Brand Name: Ariat
Product Name: Hybrid Grit Western Boots
Gender: Men's
Color: Earth/Alamo Brown
Price: $179.95
Rating: 4Rated 4 stars out of 5(33)

Nunn Bush - Centro Flex Wing Tip Oxford. Color Cognac. On sale for $79.95. MSRP $110.00. 27% off. 4.3 out of 5 stars

Tan Nunn Bush Centro Flex Wing Tip Oxford

Tan Nunn Bush Centro Flex Wing Tip Oxford

+3

Brand Name: Nunn Bush
Product Name: Centro Flex Wing Tip Oxford
Gender: Men's
Color: Cognac
Price: $79.95MSRP: $11027% OFF
Rating: 4Rated 4 stars out of 5(30)

Tommy Hilfiger - Vitus. Color Black. On sale for $59.50. MSRP $119.00. 50% off. 4.0 out of 5 stars

Black Tommy Hilfiger Vitus

Black Tommy Hilfiger Vitus

Brand Name: Tommy Hilfiger
Product Name: Vitus
Gender: Men's
Color: Black
Price: $59.50MSRP: $11950% OFF
Rating: 4Rated 4 stars out of 5(1)

PIKOLINOS - Bristol M7J-4184. Color Black. On sale for $171.00. MSRP $195.00. 12% off. 4.0 out of 5 stars

Black PIKOLINOS Bristol M7J-4184

Black PIKOLINOS Bristol M7J-4184

+2

Brand Name: PIKOLINOS
Product Name: Bristol M7J-4184
Gender: Men's
Color: Black
Price: $171MSRP: $19512% OFF
Rating: 4Rated 4 stars out of 5(1)

Tommy Hilfiger - Speer. Color Cognac. Low Stock. On sale for $54.97. MSRP $109.00. 50% off.

Low Stock

Tan Tommy Hilfiger Speer

Tan Tommy Hilfiger Speer

+2

Brand Name: Tommy Hilfiger
Product Name: Speer
Gender: Men's
Color: Cognac
Price: $54.97MSRP: $10950% OFF
Rating

Stacy Adams - Swagger Studded Ornament Loafer. Color Black. On sale for $59.95. MSRP $90.00. 33% off. 4.7 out of 5 stars

Black Stacy Adams Swagger Studded Ornament Loafer

Black Stacy Adams Swagger Studded Ornament Loafer

Brand Name: Stacy Adams
Product Name: Swagger Studded Ornament Loafer
Gender: Men's
Color: Black
Price: $59.95MSRP: $9033% OFF
Rating: 5Rated 5 stars out of 5(141)

Ariat - Sport Wide Square Toe. Color Distressed Brown. $179.95. 4.7 out of 5 stars

Brown Ariat Sport Wide Square Toe

Brown Ariat Sport Wide Square Toe

Brand Name: Ariat
Product Name: Sport Wide Square Toe
Gender: Unisex
Color: Distressed Brown
Price: $179.95
Rating: 5Rated 5 stars out of 5(167)

Timberland PRO - Endurance EV 6" Composite Safety Toe Puncture Resistant Waterproof. Color Walnut/Orange. On sale for $179.95. MSRP $195.00. 8% off. 3.7 out of 5 stars

Brown Timberland PRO Endurance EV 6" Composite Safety Toe Puncture Resistant Waterproof

Brown Timberland PRO Endurance EV 6" Composite Safety Toe Puncture Resistant Waterproof

+2

Brand Name: Timberland PRO
Product Name: Endurance EV 6" Composite Safety Toe Puncture Resistant Waterproof
Gender: Men's
Color: Walnut/Orange
Price: $179.95MSRP: $1958% OFF
Rating: 4Rated 4 stars out of 5(33)

Steve Madden - Alcona. Color Tan. Low Stock. $150.00.

Low Stock

Tan Steve Madden Alcona

Tan Steve Madden Alcona

+2

Brand Name: Steve Madden
Product Name: Alcona
Gender: Men's
Color: Tan
Price: $150
Rating

Dan Post - Neeley. Color Tan. On sale for $199.95. MSRP $229.95. 13% off. 5.0 out of 5 stars

Tan Dan Post Neeley

Tan Dan Post Neeley

Brand Name: Dan Post
Product Name: Neeley
Gender: Men's
Color: Tan
Price: $199.95MSRP: $229.9513% OFF
Rating: 5Rated 5 stars out of 5(1)

Dockers - Fairway. Color Mahogany. On sale for $49.95. MSRP $90.00. 44% off. 1.0 out of 5 stars

Mahogany Dockers Fairway

Mahogany Dockers Fairway

Brand Name: Dockers
Product Name: Fairway
Gender: Men's
Color: Mahogany
Price: $49.95MSRP: $9044% OFF
Rating: 1Rated 1 star out of 5(1)

Steve Madden - Covet. Color Black Leather. $139.99. 4.0 out of 5 stars

Black Steve Madden Covet

Black Steve Madden Covet

+2

Brand Name: Steve Madden
Product Name: Covet
Gender: Men's
Color: Black Leather
Price: $139.99
Rating: 4Rated 4 stars out of 5(3)

Tommy Hilfiger - Benty. Color Tan. On sale for $79.57. MSRP $109.00. 27% off. 4.0 out of 5 stars

Tan Tommy Hilfiger Benty

Tan Tommy Hilfiger Benty

+2

Brand Name: Tommy Hilfiger
Product Name: Benty
Gender: Men's
Color: Tan
Price: $79.57MSRP: $10927% OFF
Rating: 4Rated 4 stars out of 5(2)

Steve Madden - Privacy. Color Black Leather. $129.99. 4.5 out of 5 stars

Black Steve Madden Privacy

Black Steve Madden Privacy

Brand Name: Steve Madden
Product Name: Privacy
Gender: Men's
Color: Black Leather
Price: $129.99
Rating: 5Rated 5 stars out of 5(2)

Florsheim - Herington Canvas Plain Toe Oxford. Color Black. Low Stock. On sale for $91.31. MSRP $100.00. 9% off.

Low Stock

Black Florsheim Herington Canvas Plain Toe Oxford

Black Florsheim Herington Canvas Plain Toe Oxford

+2

Brand Name: Florsheim
Product Name: Herington Canvas Plain Toe Oxford
Gender: Men's
Color: Black
Price: $91.31MSRP: $1009% OFF
Rating

Stacy Adams - Ravelle Moc Toe Bit Slip-On. Color Green Suede. Low Stock. On sale for $106.70. MSRP $115.00. 7% off. 4.5 out of 5 stars

Low Stock

Green Stacy Adams Ravelle Moc Toe Bit Slip-On

Green Stacy Adams Ravelle Moc Toe Bit Slip-On

+2

Brand Name: Stacy Adams
Product Name: Ravelle Moc Toe Bit Slip-On
Gender: Men's
Color: Green Suede
Price: $106.70MSRP: $1157% OFF
Rating: 5Rated 5 stars out of 5(10)

Marc Joseph New York - Clarkson St. Color Brown Grainy. On sale for $89.95. MSRP $195.00. 54% off. 3.0 out of 5 stars

Brown Marc Joseph New York Clarkson St

Brown Marc Joseph New York Clarkson St

+1

Brand Name: Marc Joseph New York
Product Name: Clarkson St
Gender: Men's
Color: Brown Grainy
Price: $89.95MSRP: $19554% OFF
Rating: 3Rated 3 stars out of 5(2)

Eastland 1955 Edition - Daily Double. Color Brown Nubuck. Low Stock. On sale for $100.00. MSRP $125.00. 20% off. 3.4 out of 5 stars

Low Stock

Brown Eastland 1955 Edition Daily Double

Brown Eastland 1955 Edition Daily Double

+2

Brand Name: Eastland 1955 Edition
Product Name: Daily Double
Gender: Men's
Color: Brown Nubuck
Price: $100MSRP: $12520% OFF
Rating: 3Rated 3 stars out of 5(14)

Florsheim - Berkley Flex Penny Loafers. Color Cognac Multi. $140.00. 4.1 out of 5 stars

Tan Florsheim Berkley Flex Penny Loafers

Tan Florsheim Berkley Flex Penny Loafers

+5

Brand Name: Florsheim
Product Name: Berkley Flex Penny Loafers
Gender: Men's
Color: Cognac Multi
Price: $140
Rating: 4Rated 4 stars out of 5(239)

Stacy Adams - Wesbridge Cap Toe Lace-Up. Color Chocolate. On sale for $96.00. MSRP $120.00. 20% off. 4.0 out of 5 stars

Brown Stacy Adams Wesbridge Cap Toe Lace-Up

Brown Stacy Adams Wesbridge Cap Toe Lace-Up

+4

Brand Name: Stacy Adams
Product Name: Wesbridge Cap Toe Lace-Up
Gender: Men's
Color: Chocolate
Price: $96MSRP: $12020% OFF
Rating: 4Rated 4 stars out of 5(3)

Rockport - Charles Road Plain Toe Oxford. Color British Tan. On sale for $89.95. MSRP $119.95. 25% off. 4.2 out of 5 stars

Tan Rockport Charles Road Plain Toe Oxford

Tan Rockport Charles Road Plain Toe Oxford

+3

Brand Name: Rockport
Product Name: Charles Road Plain Toe Oxford
Gender: Men's
Color: British Tan
Price: $89.95MSRP: $119.9525% OFF
Rating: 4Rated 4 stars out of 5(10)

Stacy Adams - Tinsley Wingtip Oxford. Color Tan/Brown. On sale for $120.00. MSRP $150.00. 20% off. 4.7 out of 5 stars

Tan Stacy Adams Tinsley Wingtip Oxford

Tan Stacy Adams Tinsley Wingtip Oxford

+4

Brand Name: Stacy Adams
Product Name: Tinsley Wingtip Oxford
Gender: Men's
Color: Tan/Brown
Price: $120MSRP: $15020% OFF
Rating: 5Rated 5 stars out of 5(213)

Dockers - Whitworth. Color Black. Low Stock. On sale for $59.99. MSRP $85.00. 29% off.

Low Stock

Black Dockers Whitworth

Black Dockers Whitworth

Brand Name: Dockers
Product Name: Whitworth
Gender: Men's
Color: Black
Price: $59.99MSRP: $8529% OFF
Rating

Florsheim - Anthem Plain Toe Chukka Boots. Color Black. $145.00. 4.4 out of 5 stars

Black Florsheim Anthem Plain Toe Chukka Boots

Black Florsheim Anthem Plain Toe Chukka Boots

+4

Brand Name: Florsheim
Product Name: Anthem Plain Toe Chukka Boots
Gender: Men's
Color: Black
Price: $145
Rating: 4Rated 4 stars out of 5(11)

Florsheim - Norwalk Wingtip Oxford. Color Cognac. On sale for $109.62. MSRP $130.00. 16% off. 4.5 out of 5 stars

Tan Florsheim Norwalk Wingtip Oxford

Tan Florsheim Norwalk Wingtip Oxford

+3

Brand Name: Florsheim
Product Name: Norwalk Wingtip Oxford
Gender: Men's
Color: Cognac
Price: $109.62MSRP: $13016% OFF
Rating: 4Rated 4 stars out of 5(101)

Rockport - Maverick Plain Toe Oxford. Color New Dress Blues. On sale for $99.95. MSRP $134.95. 26% off. 4.3 out of 5 stars

Blue Rockport Maverick Plain Toe Oxford

Blue Rockport Maverick Plain Toe Oxford

+2

Brand Name: Rockport
Product Name: Maverick Plain Toe Oxford
Gender: Men's
Color: New Dress Blues
Price: $99.95MSRP: $134.9526% OFF
Rating: 4Rated 4 stars out of 5(6)

Johnston & Murphy - Baldwin Penny. Color Black. On sale for $198.00. MSRP $218.00. 9% off. 4.4 out of 5 stars

Black Johnston & Murphy Baldwin Penny

Black Johnston & Murphy Baldwin Penny

+7

Brand Name: Johnston & Murphy
Product Name: Baldwin Penny
Gender: Men's
Color: Black
Price: $198MSRP: $2189% OFF
Rating: 4Rated 4 stars out of 5(52)

Johnston & Murphy - Upton Knit Wing Tip. Color Gray Knit. On sale for $135.15. MSRP $159.00. 15% off. 4.2 out of 5 stars

Gray Johnston & Murphy Upton Knit Wing Tip

Gray Johnston & Murphy Upton Knit Wing Tip

+3

Brand Name: Johnston & Murphy
Product Name: Upton Knit Wing Tip
Gender: Men's
Color: Gray Knit
Price: $135.15MSRP: $15915% OFF
Rating: 4Rated 4 stars out of 5(67)

Florsheim - Highland Canvas Plain Toe Oxford. Color Blalck Canvas/White Sole. $110.00. 4.7 out of 5 stars

Black Florsheim Highland Canvas Plain Toe Oxford

Black Florsheim Highland Canvas Plain Toe Oxford

+2

Brand Name: Florsheim
Product Name: Highland Canvas Plain Toe Oxford
Gender: Men's
Color: Blalck Canvas/White Sole
Price: $110
Rating: 5Rated 5 stars out of 5(126)

Johnston & Murphy - Upton Knit Plain Toe. Color Gray Knit. On sale for $119.99. MSRP $159.00. 25% off. 4.1 out of 5 stars

Gray Johnston & Murphy Upton Knit Plain Toe

Gray Johnston & Murphy Upton Knit Plain Toe

+3

Brand Name: Johnston & Murphy
Product Name: Upton Knit Plain Toe
Gender: Men's
Color: Gray Knit
Price: $119.99MSRP: $15925% OFF
Rating: 4Rated 4 stars out of 5(68)

Stacy Adams - Kaylor Penny Slip-On Loafer. Color Black. On sale for $99.90. MSRP $130.00. 23% off. 4.7 out of 5 stars

Black Stacy Adams Kaylor Penny Slip-On Loafer

Black Stacy Adams Kaylor Penny Slip-On Loafer

Brand Name: Stacy Adams
Product Name: Kaylor Penny Slip-On Loafer
Gender: Men's
Color: Black
Price: $99.90MSRP: $13023% OFF
Rating: 5Rated 5 stars out of 5(30)

Rockport - Style Leader 2 Apron Toe. Color Black Waxed Calf. On sale for $99.95. MSRP $129.95. 23% off. 4.3 out of 5 stars

Black Rockport Style Leader 2 Apron Toe

Black Rockport Style Leader 2 Apron Toe

+2

Brand Name: Rockport
Product Name: Style Leader 2 Apron Toe
Gender: Men's
Color: Black Waxed Calf
Price: $99.95MSRP: $129.9523% OFF
Rating: 4Rated 4 stars out of 5(179)

Clarks - Tilden Free. Color Black. On sale for $53.97. MSRP $105.00. 49% off. 4.0 out of 5 stars

Black Clarks Tilden Free

Black Clarks Tilden Free

+2

Brand Name: Clarks
Product Name: Tilden Free
Gender: Men's
Color: Black
Price: $53.97MSRP: $10549% OFF
Rating: 4Rated 4 stars out of 5(81)

Dockers - Fairway. Color Black. On sale for $49.95. MSRP $90.00. 44% off. 4.0 out of 5 stars

Black Dockers Fairway

Black Dockers Fairway

Brand Name: Dockers
Product Name: Fairway
Gender: Men's
Color: Black
Price: $49.95MSRP: $9044% OFF
Rating: 4Rated 4 stars out of 5(1)

Ariat - Hybrid Rancher. Color Distressed Brown. $199.95. 4.5 out of 5 stars

Brown Ariat Hybrid Rancher

Brown Ariat Hybrid Rancher

+2

Brand Name: Ariat
Product Name: Hybrid Rancher
Gender: Men's
Color: Distressed Brown
Price: $199.95
Rating: 4Rated 4 stars out of 5(428)

Ariat - Ariat Rambler. Color Wicker. $189.95. 4.6 out of 5 stars

Tan Ariat Ariat Rambler

Tan Ariat Ariat Rambler

+3

Brand Name: Ariat
Product Name: Ariat Rambler
Gender: Men's
Color: Wicker
Price: $189.95
Rating: 5Rated 5 stars out of 5(5317)

Florsheim - Forge Plain Toe Gore Boots. Color Black. $130.00. 4.1 out of 5 stars

Black Florsheim Forge Plain Toe Gore Boots

Black Florsheim Forge Plain Toe Gore Boots

+3

Brand Name: Florsheim
Product Name: Forge Plain Toe Gore Boots
Gender: Men's
Color: Black
Price: $130
Rating: 4Rated 4 stars out of 5(28)

Stacy Adams - Karson Wing Tip Double Monk Strap. Color Black. On sale for $94.99. MSRP $130.00. 27% off. 4.4 out of 5 stars

Black Stacy Adams Karson Wing Tip Double Monk Strap

Black Stacy Adams Karson Wing Tip Double Monk Strap

Brand Name: Stacy Adams
Product Name: Karson Wing Tip Double Monk Strap
Gender: Men's
Color: Black
Price: $94.99MSRP: $13027% OFF
Rating: 4Rated 4 stars out of 5(24)

. Florsheim - Montinaro Double Monk Strap. Color Saddle Tan Smooth. On sale for $89.95. MSRP $110.00. 18% off. 4.0 out of 5 stars

Brown Florsheim Montinaro Double Monk Strap

Brown Florsheim Montinaro Double Monk Strap

+2

Brand Name: Florsheim
Product Name: Montinaro Double Monk Strap
Gender: Men's
Color: Saddle Tan Smooth
Price: $89.95MSRP: $11018% OFF
Rating: 4Rated 4 stars out of 5(90)

Cole Haan - Hawthorne Penny Loafer. Color Habana. On sale for $135.01. MSRP $148.00. 9% off. 3.7 out of 5 stars

Brown Cole Haan Hawthorne Penny Loafer

Brown Cole Haan Hawthorne Penny Loafer

Brand Name: Cole Haan
Product Name: Hawthorne Penny Loafer
Gender: Men's
Color: Habana
Price: $135.01MSRP: $1489% OFF
Rating: 4Rated 4 stars out of 5(7)

Stacy Adams - Marligan Wing Tip Oxford. Color Dark Gray. On sale for $99.95. MSRP $130.00. 23% off. 4.7 out of 5 stars

Gray Stacy Adams Marligan Wing Tip Oxford

Gray Stacy Adams Marligan Wing Tip Oxford

+3

Brand Name: Stacy Adams
Product Name: Marligan Wing Tip Oxford
Gender: Men's
Color: Dark Gray
Price: $99.95MSRP: $13023% OFF
Rating: 5Rated 5 stars out of 5(20)

Cole Haan - Pinch Prep Penny Loafer. Color Birchbeige Suede/Dark Chocolate. On sale for $78.00. MSRP $130.00. 40% off. 3.9 out of 5 stars

Beige Cole Haan Pinch Prep Penny Loafer

Beige Cole Haan Pinch Prep Penny Loafer

+4

Brand Name: Cole Haan
Product Name: Pinch Prep Penny Loafer
Gender: Men's
Color: Birchbeige Suede/Dark Chocolate
Price: $78MSRP: $13040% OFF
Rating: 4Rated 4 stars out of 5(12)

Johnston & Murphy - Upton Chelsea Boots. Color Tan Full Grain. On sale for $119.99. MSRP $179.00. 33% off. 2.0 out of 5 stars

Tan Johnston & Murphy Upton Chelsea Boots

Tan Johnston & Murphy Upton Chelsea Boots

+2

Brand Name: Johnston & Murphy
Product Name: Upton Chelsea Boots
Gender: Men's
Color: Tan Full Grain
Price: $119.99MSRP: $17933% OFF
Rating: 2Rated 2 stars out of 5(1)

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

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)

Martin Dingman - Maxwell Penny. Color Black. Low Stock. On sale for $177.00. MSRP $295.00. 40% off.

Low Stock

Black Martin Dingman Maxwell Penny

Black Martin Dingman Maxwell Penny

+2

Brand Name: Martin Dingman
Product Name: Maxwell Penny
Gender: Men's
Color: Black
Price: $177MSRP: $29540% OFF
Rating

ECCO - Citytray Plain Toe Tie. Color Cognac. $199.95. 3.3 out of 5 stars

Tan ECCO Citytray Plain Toe Tie

Tan ECCO Citytray Plain Toe Tie

+2

Brand Name: ECCO
Product Name: Citytray Plain Toe Tie
Gender: Men's
Color: Cognac
Price: $199.95
Rating: 3Rated 3 stars out of 5(9)

Stacy Adams - Spratley Saddle Slip-On. Color Royal Blue. On sale for $72.00. MSRP $90.00. 20% off. 5.0 out of 5 stars

Blue Stacy Adams Spratley Saddle Slip-On

Blue Stacy Adams Spratley Saddle Slip-On

Brand Name: Stacy Adams
Product Name: Spratley Saddle Slip-On
Gender: Men's
Color: Royal Blue
Price: $72MSRP: $9020% OFF
Rating: 5Rated 5 stars out of 5(11)

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