Winter Wins
Performance picks built for champions—on & off the mountain.
Shop Now

Skip to search results Skip to filters Skip to sort Skip to selected filters

Men's Penny Keeper Leather Shoes

29 items found

Filters

Search Results

Frye - Tyler Flex Penny. Color Mushroom. Low Stock. On sale for $178.20. MSRP $198.00. 10% off. 4.0 out of 5 stars

Low Stock

Neutral Frye Tyler Flex Penny

Neutral Frye Tyler Flex Penny

+5

Brand Name: Frye
Product Name: Tyler Flex Penny
Gender: Men's
Color: Mushroom
Price: $178.20MSRP: $19810% OFF
Rating: 4Rated 4 stars out of 5(10)

Florsheim - Sorrento Moc Toe Penny Loafers. Color Black Smooth. On sale for $109.95. MSRP $145.00. 24% off. 4.3 out of 5 stars

Black Florsheim Sorrento Moc Toe Penny Loafers

Black Florsheim Sorrento Moc Toe Penny Loafers

+2

Brand Name: Florsheim
Product Name: Sorrento Moc Toe Penny Loafers
Gender: Men's
Color: Black Smooth
Price: $109.95MSRP: $14524% OFF
Rating: 4Rated 4 stars out of 5(61)

Marc Joseph New York - Nebraska. Color Wine Grainy. On sale for $89.95. MSRP $185.00. 51% off. 4.0 out of 5 stars

Red Marc Joseph New York Nebraska

Red Marc Joseph New York Nebraska

+8

Brand Name: Marc Joseph New York
Product Name: Nebraska
Gender: Men's
Color: Wine Grainy
Price: $89.95MSRP: $18551% OFF
Rating: 4Rated 4 stars out of 5(18)

Johnston & Murphy - Dayton Penny Loafer. Color Brown. On sale for $159.99. MSRP $245.00. 35% off. 5.0 out of 5 stars

Brown Johnston & Murphy Dayton Penny Loafer

Brown Johnston & Murphy Dayton Penny Loafer

Brand Name: Johnston & Murphy
Product Name: Dayton Penny Loafer
Gender: Men's
Color: Brown
Price: $159.99MSRP: $24535% OFF
Rating: 5Rated 5 stars out of 5(7)

Johnston & Murphy - Hayes Penny Loafers. Color Burgundy. $119.90. 4.1 out of 5 stars

Burgundy Johnston & Murphy Hayes Penny Loafers

Burgundy Johnston & Murphy Hayes Penny Loafers

+2

Brand Name: Johnston & Murphy
Product Name: Hayes Penny Loafers
Gender: Men's
Color: Burgundy
Price: $119.90
Rating: 4Rated 4 stars out of 5(117)

Polo Ralph Lauren - Alston Penny. Color Tan. $178.00. 4.0 out of 5 stars

Tan Polo Ralph Lauren Alston Penny

Tan Polo Ralph Lauren Alston Penny

+2

Brand Name: Polo Ralph Lauren
Product Name: Alston Penny
Gender: Men's
Color: Tan
Price: $178
Rating: 4Rated 4 stars out of 5(2)

Steve Madden - Belleaire. Color Black. Low Stock. $140.00.

Low Stock

Black Steve Madden Belleaire

Black Steve Madden Belleaire

+2

Brand Name: Steve Madden
Product Name: Belleaire
Gender: Men's
Color: Black
Price: $140
Rating

Nunn Bush - Lincoln Penny Loafer. Color Burgundy Polished. On sale for $69.95. MSRP $100.00. 30% off. 4.2 out of 5 stars

Burgundy Nunn Bush Lincoln Penny Loafer

Burgundy Nunn Bush Lincoln Penny Loafer

+2 colors/patterns

Brand Name: Nunn Bush
Product Name: Lincoln Penny Loafer
Gender: Men's
Color: Burgundy Polished
Price: $69.95MSRP: $10030% OFF
Rating: 4Rated 4 stars out of 5(329)

Cole Haan - Wyatt Penny Driver. Color British Tan/Nicotine. $140.00. 4.3 out of 5 stars

Brown Cole Haan Wyatt Penny Driver

Brown Cole Haan Wyatt Penny Driver

+2

Brand Name: Cole Haan
Product Name: Wyatt Penny Driver
Gender: Men's
Color: British Tan/Nicotine
Price: $140
Rating: 4Rated 4 stars out of 5(283)

Samuel Hubbard - Free Spirit for Him. Color Brown Leather. $195.00. 3.5 out of 5 stars

Brown Samuel Hubbard Free Spirit for Him

Brown Samuel Hubbard Free Spirit for Him

+2

Brand Name: Samuel Hubbard
Product Name: Free Spirit for Him
Gender: Men's
Color: Brown Leather
Price: $195
Rating: 4Rated 4 stars out of 5(4)

Johnston & Murphy - Emmett Penny. Color Dark Tan Full Grain. $99.90. 4.6 out of 5 stars

Tan Johnston & Murphy Emmett Penny

Tan Johnston & Murphy Emmett Penny

Brand Name: Johnston & Murphy
Product Name: Emmett Penny
Gender: Men's
Color: Dark Tan Full Grain
Price: $99.90
Rating: 5Rated 5 stars out of 5(70)

Florsheim - Zaffiro Moc Toe Penny Loafers. Color Black. $144.99. 4.7 out of 5 stars

Black Florsheim Zaffiro Moc Toe Penny Loafers

Black Florsheim Zaffiro Moc Toe Penny Loafers

+2

Brand Name: Florsheim
Product Name: Zaffiro Moc Toe Penny Loafers
Gender: Men's
Color: Black
Price: $144.99
Rating: 5Rated 5 stars out of 5(19)

Marc Joseph New York - River Road. Color Cognac Grainy. On sale for $69.95. MSRP $185.00. 62% off. 5.0 out of 5 stars

Brown Marc Joseph New York River Road

Brown Marc Joseph New York River Road

+3

Brand Name: Marc Joseph New York
Product Name: River Road
Gender: Men's
Color: Cognac Grainy
Price: $69.95MSRP: $18562% OFF
Rating: 5Rated 5 stars out of 5(1)

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

Low Stock

Brown Martin Dingman Bill Penny

Brown Martin Dingman Bill Penny

+2

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

ECCO - S Lite Moc Penny Loafers. Color Cognac. $174.95. 4.0 out of 5 stars

Tan ECCO S Lite Moc Penny Loafers

Tan ECCO S Lite Moc Penny Loafers

+2

Brand Name: ECCO
Product Name: S Lite Moc Penny Loafers
Gender: Men's
Color: Cognac
Price: $174.95
Rating: 4Rated 4 stars out of 5(4)

Marc Joseph New York - Valley Road 2.0. Color Cognac Grainy. Low Stock. On sale for $79.95. MSRP $195.00. 59% off. 4.1 out of 5 stars

Low Stock

Brown Marc Joseph New York Valley Road 2.0

Brown Marc Joseph New York Valley Road 2.0

+3

Brand Name: Marc Joseph New York
Product Name: Valley Road 2.0
Gender: Men's
Color: Cognac Grainy
Price: $79.95MSRP: $19559% OFF
Rating: 4Rated 4 stars out of 5(10)

johnnie-O - Clubhouse Penny Loafers. Color Tan. Low Stock. $198.00.

Low Stock

Tan johnnie-O Clubhouse Penny Loafers

Tan johnnie-O Clubhouse Penny Loafers

Brand Name: johnnie-O
Product Name: Clubhouse Penny Loafers
Gender: Men's
Color: Tan
Price: $198
Rating

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

Low Stock

Brown Martin Dingman Maxwell Penny

Brown Martin Dingman Maxwell Penny

+2

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

Florsheim - Midtown Penny Slip-On. Color Cognac Smooth. On sale for $99.95. MSRP $140.00. 29% off. 4.4 out of 5 stars

Neutral Florsheim Midtown Penny Slip-On

Neutral Florsheim Midtown Penny Slip-On

+2

Brand Name: Florsheim
Product Name: Midtown Penny Slip-On
Gender: Men's
Color: Cognac Smooth
Price: $99.95MSRP: $14029% OFF
Rating: 4Rated 4 stars out of 5(113)

Carlos by Carlos Santana - Ritchie Driver Loafers. Color Navy Calf Nubuck. Low Stock. On sale for $79.97. MSRP $88.95. 10% off. 3.9 out of 5 stars

Low Stock

Navy Carlos by Carlos Santana Ritchie Driver Loafers

Navy Carlos by Carlos Santana Ritchie Driver Loafers

+2

Brand Name: Carlos by Carlos Santana
Product Name: Ritchie Driver Loafers
Gender: Men's
Color: Navy Calf Nubuck
Price: $79.97MSRP: $88.9510% OFF
Rating: 4Rated 4 stars out of 5(8)

Sperry - AO Penny Double Sole MM. Color Navy. On sale for $100.01. MSRP $109.95. 9% off. 4.4 out of 5 stars

Navy Sperry AO Penny Double Sole MM

Navy Sperry AO Penny Double Sole MM

Brand Name: Sperry
Product Name: AO Penny Double Sole MM
Gender: Men's
Color: Navy
Price: $100.01MSRP: $109.959% OFF
Rating: 4Rated 4 stars out of 5(31)

Gordon Rush - Parkside. Color Navy Suede. Low Stock. $129.90. 2.0 out of 5 stars

Low Stock

Blue Gordon Rush Parkside

Blue Gordon Rush Parkside

Brand Name: Gordon Rush
Product Name: Parkside
Gender: Men's
Color: Navy Suede
Price: $129.90
Rating: 2Rated 2 stars out of 5(2)

Anthony Veer - Sherman Penny Loafers. Color Honey Brown. Low Stock. On sale for $104.57. MSRP $164.95. 37% off. 4.0 out of 5 stars

Low Stock

Brown Anthony Veer Sherman Penny Loafers

Brown Anthony Veer Sherman Penny Loafers

Brand Name: Anthony Veer
Product Name: Sherman Penny Loafers
Gender: Men's
Color: Honey Brown
Price: $104.57MSRP: $164.9537% OFF
Rating: 4Rated 4 stars out of 5(101)

. Andre Assous - Mateo Loafers. Color Sand Suede. $189.00.

Tan Andre Assous Mateo Loafers

Tan Andre Assous Mateo Loafers

+2

Brand Name: Andre Assous
Product Name: Mateo Loafers
Gender: Men's
Color: Sand Suede
Price: $189
Rating

Anthony Veer - Gerry Penny Loafers. Color Tan. Low Stock. On sale for $140.99. MSRP $199.95. 29% off. 4.0 out of 5 stars

Low Stock

Tan Anthony Veer Gerry Penny Loafers

Tan Anthony Veer Gerry Penny Loafers

Brand Name: Anthony Veer
Product Name: Gerry Penny Loafers
Gender: Men's
Color: Tan
Price: $140.99MSRP: $199.9529% OFF
Rating: 4Rated 4 stars out of 5(134)

Martin Dingman - All American Penny. Color Oak. Low Stock. On sale for $177.00. MSRP $295.00. 40% off. 3.0 out of 5 stars

Low Stock

Brown Martin Dingman All American Penny

Brown Martin Dingman All American Penny

Brand Name: Martin Dingman
Product Name: All American Penny
Gender: Men's
Color: Oak
Price: $177MSRP: $29540% OFF
Rating: 3Rated 3 stars out of 5(2)

Marc Joseph New York - Union Street 2. Color Cafe Grainy. Low Stock. On sale for $139.50. MSRP $155.00. 10% off. 4.8 out of 5 stars

Low Stock

Brown Marc Joseph New York Union Street 2

Brown Marc Joseph New York Union Street 2

+2

Brand Name: Marc Joseph New York
Product Name: Union Street 2
Gender: Men's
Color: Cafe Grainy
Price: $139.50MSRP: $15510% OFF
Rating: 5Rated 5 stars out of 5(4)

Polo Ralph Lauren - Anders Penny. Color Black. $168.00. 3.0 out of 5 stars

Black Polo Ralph Lauren Anders Penny

Black Polo Ralph Lauren Anders Penny

+2

Brand Name: Polo Ralph Lauren
Product Name: Anders Penny
Gender: Men's
Color: Black
Price: $168
Rating: 3Rated 3 stars out of 5(2)

Johnston & Murphy - Baldwin Penny. Color Snuff English Suede. Low Stock. On sale for $196.20. MSRP $218.00. 10% off. 4.4 out of 5 stars

Low Stock

Brown Johnston & Murphy Baldwin Penny

Brown Johnston & Murphy Baldwin Penny

+7

Brand Name: Johnston & Murphy
Product Name: Baldwin Penny
Gender: Men's
Color: Snuff English Suede
Price: $196.20MSRP: $21810% OFF
Rating: 4Rated 4 stars out of 5(52)

Join Our Email List

Never miss out on latest drops & sales—plus, new subscribers get 10% off.*

*One code per email address.