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

Medium Size Penny Keeper Leather Closed Toe Shoes

48 items found

Sort By

Your Selections

Search Results

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

Black Steve Madden Belleaire

Black Steve Madden Belleaire

+2

Brand Name: Steve Madden
Product Name: Belleaire
Gender: Men's
Color: Black
Price: $140.00
Rating

Polo Ralph Lauren - Alston Penny. Color Black. $178.00. 3.0 out of 5 stars

Black Polo Ralph Lauren Alston Penny

Black Polo Ralph Lauren Alston Penny

+3

Brand Name: Polo Ralph Lauren
Product Name: Alston Penny
Gender: Men's
Color: Black
Price: $178.00
Rating: 3Rated 3 stars out of 5(1)

Florsheim - Sorrento Moc Toe Penny Loafer. Color Black Smooth. On sale for $109.95. MSRP $145.00. 24% off. 4.2 out of 5 stars

Black Florsheim Sorrento Moc Toe Penny Loafer

Black Florsheim Sorrento Moc Toe Penny Loafer

+2

Brand Name: Florsheim
Product Name: Sorrento Moc Toe Penny Loafer
Gender: Men's
Color: Black Smooth
Price: $109.95MSRP: $145.0024% OFF
Rating: 4Rated 4 stars out of 5(48)

Johnston & Murphy - Hayes Penny Loafer. Color Black. $119.85. 4.1 out of 5 stars

Black Johnston & Murphy Hayes Penny Loafer

Black Johnston & Murphy Hayes Penny Loafer

+2

Brand Name: Johnston & Murphy
Product Name: Hayes Penny Loafer
Gender: Men's
Color: Black
Price: $119.85
Rating: 4Rated 4 stars out of 5(117)

Frye - Tyler Flex Penny. Color Black. Low Stock. On sale for $99.00. MSRP $198.00. 50% off. 4.4 out of 5 stars

Low Stock

Black Frye Tyler Flex Penny

Black Frye Tyler Flex Penny

+5

Brand Name: Frye
Product Name: Tyler Flex Penny
Gender: Men's
Color: Black
Price: $99.00MSRP: $198.0050% OFF
Rating: 4Rated 4 stars out of 5(5)

Marc Joseph New York - Nebraska. Color Black Napa. On sale for $89.95. MSRP $185.00. 51% off. 3.9 out of 5 stars

Black Marc Joseph New York Nebraska

Black Marc Joseph New York Nebraska

+8

Brand Name: Marc Joseph New York
Product Name: Nebraska
Gender: Men's
Color: Black Napa
Price: $89.95MSRP: $185.0051% OFF
Rating: 4Rated 4 stars out of 5(14)

Johnston & Murphy - Baldwin Penny. Color Taupe Suede. $217.95. 4.4 out of 5 stars

Taupe Johnston & Murphy Baldwin Penny

Taupe Johnston & Murphy Baldwin Penny

+7

Brand Name: Johnston & Murphy
Product Name: Baldwin Penny
Gender: Men's
Color: Taupe Suede
Price: $217.95
Rating: 4Rated 4 stars out of 5(51)

Bruno Magli - Lastra. Color Black. Low Stock. $298.00.

Low Stock

Black Bruno Magli Lastra

Black Bruno Magli Lastra

+2

Brand Name: Bruno Magli
Product Name: Lastra
Gender: Men's
Color: Black
Price: $298.00
Rating

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

Black Florsheim Zaffiro Moc Toe Penny Loafer

Black Florsheim Zaffiro Moc Toe Penny Loafer

+2

Brand Name: Florsheim
Product Name: Zaffiro Moc Toe Penny Loafer
Gender: Men's
Color: Black
Price: $144.99
Rating: 5Rated 5 stars out of 5(16)

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

Brown Polo Ralph Lauren Anders Penny

Brown Polo Ralph Lauren Anders Penny

+3

Brand Name: Polo Ralph Lauren
Product Name: Anders Penny
Gender: Men's
Color: Brown
Price: $168.00
Rating: 3Rated 3 stars out of 5(2)

AllSaints - Jago Loafer. Color Tan. Low Stock. On sale for $89.70. MSRP $299.00. 70% off.

Low Stock

Tan AllSaints Jago Loafer

Tan AllSaints Jago Loafer

Brand Name: AllSaints
Product Name: Jago Loafer
Gender: Men's
Color: Tan
Price: $89.70MSRP: $299.0070% OFF
Rating

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: $185.0062% OFF
Rating: 5Rated 5 stars out of 5(1)

Carlos by Carlos Santana - Ritchie Driver Loafer. Color Olive Calf Nubuck. Low Stock. $88.95. 3.9 out of 5 stars

Low Stock

Brown Carlos by Carlos Santana Ritchie Driver Loafer

Brown Carlos by Carlos Santana Ritchie Driver Loafer

+2

Brand Name: Carlos by Carlos Santana
Product Name: Ritchie Driver Loafer
Gender: Men's
Color: Olive Calf Nubuck
Price: $88.95
Rating: 4Rated 4 stars out of 5(8)

ECCO - S Lite Moc Penny Loafer. Color Black. $174.95. 4.0 out of 5 stars

Black ECCO S Lite Moc Penny Loafer

Black ECCO S Lite Moc Penny Loafer

+2

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

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

Black Nunn Bush Lincoln Penny Loafer

Black Nunn Bush Lincoln Penny Loafer

+2 colors/patterns

Brand Name: Nunn Bush
Product Name: Lincoln Penny Loafer
Gender: Men's
Color: Black Polished
Price: $69.95MSRP: $100.0030% OFF
Rating: 4Rated 4 stars out of 5(319)

Bruno Magli - Raging Penny. Color Black. $395.00. 5.0 out of 5 stars

Black Bruno Magli Raging Penny

Black Bruno Magli Raging Penny

Brand Name: Bruno Magli
Product Name: Raging Penny
Gender: Men's
Color: Black
Price: $395.00
Rating: 5Rated 5 stars out of 5(1)

Marc Joseph New York - Union Street 2. Color Black Grainy. $155.00. 4.8 out of 5 stars

Black Marc Joseph New York Union Street 2

Black Marc Joseph New York Union Street 2

+3

Brand Name: Marc Joseph New York
Product Name: Union Street 2
Gender: Men's
Color: Black Grainy
Price: $155.00
Rating: 5Rated 5 stars out of 5(4)

To Boot New York - Ravello. Color Black. On sale for $399.00. MSRP $425.00. 6% off.

Black To Boot New York Ravello

Black To Boot New York Ravello

Brand Name: To Boot New York
Product Name: Ravello
Gender: Men's
Color: Black
Price: $399.00MSRP: $425.006% OFF
Rating

La Canadienne - Alvin. Color Tan Leather. Low Stock. On sale for $70.00. MSRP $350.00. 80% off. 2.0 out of 5 stars

Low Stock

Tan La Canadienne Alvin

Tan La Canadienne Alvin

Brand Name: La Canadienne
Product Name: Alvin
Gender: Men's
Color: Tan Leather
Price: $70.00MSRP: $350.0080% OFF
Rating: 2Rated 2 stars out of 5(2)

Cole Haan - Wyatt Penny Driver. Color British Tan/Nicotine. On sale for $112.00. MSRP $140.00. 20% off. 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: $112.00MSRP: $140.0020% OFF
Rating: 4Rated 4 stars out of 5(282)

Sperry - Authentic Original Penny. Color Navy. On sale for $108.19. MSRP $109.95. 2% off. 4.4 out of 5 stars

Navy Sperry Authentic Original Penny

Navy Sperry Authentic Original Penny

Brand Name: Sperry
Product Name: Authentic Original Penny
Gender: Men's
Color: Navy
Price: $108.19MSRP: $109.952% OFF
Rating: 4Rated 4 stars out of 5(31)

Martin Dingman - Maxwell Penny. Color Whiskey. Low Stock. $295.00.

Low Stock

Brown Martin Dingman Maxwell Penny

Brown Martin Dingman Maxwell Penny

Brand Name: Martin Dingman
Product Name: Maxwell Penny
Gender: Men's
Color: Whiskey
Price: $295.00
Rating

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: $195.00
Rating: 4Rated 4 stars out of 5(4)

Allen Edmonds - Randolph. Color Coffee. On sale for $299.00. MSRP $450.00. 34% off. 3.9 out of 5 stars

Brown Allen Edmonds Randolph

Brown Allen Edmonds Randolph

+2

Brand Name: Allen Edmonds
Product Name: Randolph
Gender: Men's
Color: Coffee
Price: $299.00MSRP: $450.0034% OFF
Rating: 4Rated 4 stars out of 5(35)

Martin Dingman - All American Penny. Color Chestnut. Low Stock. $295.00. 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: Chestnut
Price: $295.00
Rating: 3Rated 3 stars out of 5(2)

Sperry - Topsfield Penny Loafer. Color Black 1. Low Stock. On sale for $120.00. MSRP $130.00. 8% off. 4.2 out of 5 stars

Low Stock

Black Sperry Topsfield Penny Loafer

Black Sperry Topsfield Penny Loafer

Brand Name: Sperry
Product Name: Topsfield Penny Loafer
Gender: Men's
Color: Black 1
Price: $120.00MSRP: $130.008% OFF
Rating: 4Rated 4 stars out of 5(28)

Martin Dingman - Bill Penny. Color Chestnut. $295.00.

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: $295.00
Rating

Johnston & Murphy - Dayton Woven Penny. Color Brown Italian Calfskin. On sale for $173.95. MSRP $245.00. 29% off. 4.1 out of 5 stars

Brown Johnston & Murphy Dayton Woven Penny

Brown Johnston & Murphy Dayton Woven Penny

Brand Name: Johnston & Murphy
Product Name: Dayton Woven Penny
Gender: Men's
Color: Brown Italian Calfskin
Price: $173.95MSRP: $245.0029% OFF
Rating: 4Rated 4 stars out of 5(15)

Johnston & Murphy - Dayton Penny Loafer. Color Brown. On sale for $173.95. MSRP $245.00. 29% 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: $173.95MSRP: $245.0029% OFF
Rating: 5Rated 5 stars out of 5(7)

Allen Edmonds - Randolph 2.0 Slip-on Sneaker. Color Black Leather. On sale for $279.00. MSRP $350.00. 20% off. 3.5 out of 5 stars

Black Allen Edmonds Randolph 2.0 Slip-on Sneaker

Black Allen Edmonds Randolph 2.0 Slip-on Sneaker

+5

Brand Name: Allen Edmonds
Product Name: Randolph 2.0 Slip-on Sneaker
Gender: Men's
Color: Black Leather
Price: $279.00MSRP: $350.0020% OFF
Rating: 4Rated 4 stars out of 5(2)

johnnie-O - Clubhouse Penny Loafer. Color Tan. $198.00.

Tan johnnie-O Clubhouse Penny Loafer

Tan johnnie-O Clubhouse Penny Loafer

Brand Name: johnnie-O
Product Name: Clubhouse Penny Loafer
Gender: Men's
Color: Tan
Price: $198.00
Rating

Magnanni - Ramiro II. Color Torba Suede. Low Stock. On sale for $382.50. MSRP $425.00. 10% off. 5.0 out of 5 stars

Low Stock

Brown Magnanni Ramiro II

Brown Magnanni Ramiro II

Brand Name: Magnanni
Product Name: Ramiro II
Gender: Men's
Color: Torba Suede
Price: $382.50MSRP: $425.0010% OFF
Rating: 5Rated 5 stars out of 5(7)

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: $195.0059% OFF
Rating: 4Rated 4 stars out of 5(10)

Allen Edmonds - Randolph. Color Black Calf. On sale for $299.00. MSRP $450.00. 34% off. 3.5 out of 5 stars

Black Allen Edmonds Randolph

Black Allen Edmonds Randolph

Brand Name: Allen Edmonds
Product Name: Randolph
Gender: Men's
Color: Black Calf
Price: $299.00MSRP: $450.0034% OFF
Rating: 3Rated 3 stars out of 5(11)

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: $140.0029% OFF
Rating: 4Rated 4 stars out of 5(113)

Bruno Magli - Tonio. Color Dark Brown Cervo. On sale for $296.25. MSRP $395.00. 25% off. 5.0 out of 5 stars

Brown Bruno Magli Tonio

Brown Bruno Magli Tonio

Brand Name: Bruno Magli
Product Name: Tonio
Gender: Men's
Color: Dark Brown Cervo
Price: $296.25MSRP: $395.0025% OFF
Rating: 5Rated 5 stars out of 5(2)

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)

Allen Edmonds - Supersport Penny. Color Walnut. $300.00. 3.7 out of 5 stars

Brown Allen Edmonds Supersport Penny

Brown Allen Edmonds Supersport Penny

+2

Brand Name: Allen Edmonds
Product Name: Supersport Penny
Gender: Men's
Color: Walnut
Price: $300.00
Rating: 4Rated 4 stars out of 5(29)

COACH - Declan Loafer. Color Saddle. On sale for $222.05. MSRP $250.00. 11% off. 4.8 out of 5 stars

Brown COACH Declan Loafer

Brown COACH Declan Loafer

Brand Name: COACH
Product Name: Declan Loafer
Gender: Men's
Color: Saddle
Price: $222.05MSRP: $250.0011% OFF
Rating: 5Rated 5 stars out of 5(4)

To Boot New York - Moore. Color Blue. Low Stock. On sale for $239.40. MSRP $399.00. 40% off. 4.3 out of 5 stars

Low Stock

Blue To Boot New York Moore

Blue To Boot New York Moore

+3

Brand Name: To Boot New York
Product Name: Moore
Gender: Men's
Color: Blue
Price: $239.40MSRP: $399.0040% OFF
Rating: 4Rated 4 stars out of 5(3)

Allen Edmonds - Supersprtpen. Color Light Grey. Low Stock. $300.00. 4.0 out of 5 stars

Low Stock

Gray Allen Edmonds Supersprtpen

Gray Allen Edmonds Supersprtpen

Brand Name: Allen Edmonds
Product Name: Supersprtpen
Gender: Men's
Color: Light Grey
Price: $300.00
Rating: 4Rated 4 stars out of 5(1)

Allen Edmonds - Randolph Sneaker. Color Black. Low Stock. $300.00. 4.3 out of 5 stars

Low Stock

Black Allen Edmonds Randolph Sneaker

Black Allen Edmonds Randolph Sneaker

Brand Name: Allen Edmonds
Product Name: Randolph Sneaker
Gender: Men's
Color: Black
Price: $300.00
Rating: 4Rated 4 stars out of 5(57)

Anthony Veer - Sherman Penny Loafer. Color Chocolate Brown. Low Stock. On sale for $109.97. MSRP $149.90. 27% off. 4.0 out of 5 stars

Low Stock

Brown Anthony Veer Sherman Penny Loafer

Brown Anthony Veer Sherman Penny Loafer

Brand Name: Anthony Veer
Product Name: Sherman Penny Loafer
Gender: Men's
Color: Chocolate Brown
Price: $109.97MSRP: $149.9027% OFF
Rating: 4Rated 4 stars out of 5(101)

Anthony Veer - Gerry Penny Loafer. Color Tan. Low Stock. $199.95. 4.0 out of 5 stars

Low Stock

Tan Anthony Veer Gerry Penny Loafer

Tan Anthony Veer Gerry Penny Loafer

Brand Name: Anthony Veer
Product Name: Gerry Penny Loafer
Gender: Men's
Color: Tan
Price: $199.95
Rating: 4Rated 4 stars out of 5(134)

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)

To Boot New York - Idris. Color Blue Suede. Low Stock. On sale for $178.75. MSRP $325.00. 45% off. 5.0 out of 5 stars

Low Stock

Blue To Boot New York Idris

Blue To Boot New York Idris

Brand Name: To Boot New York
Product Name: Idris
Gender: Men's
Color: Blue Suede
Price: $178.75MSRP: $325.0045% OFF
Rating: 5Rated 5 stars out of 5(1)

To Boot New York - Alek. Color Moro. Low Stock. $425.00. 4.0 out of 5 stars

Low Stock

Brown To Boot New York Alek

Brown To Boot New York Alek

Brand Name: To Boot New York
Product Name: Alek
Gender: Men's
Color: Moro
Price: $425.00
Rating: 4Rated 4 stars out of 5(3)

Marc Joseph New York - East Village Mens. Color Black Napa. Low Stock. $175.00.

Low Stock

Black Marc Joseph New York East Village Mens

Black Marc Joseph New York East Village Mens

Brand Name: Marc Joseph New York
Product Name: East Village Mens
Gender: Men's
Color: Black Napa
Price: $175.00
Rating

Join Our Email List

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

*One code per email address.