Spring Forward
Warm days, full calendars & the perfect shoes for everything ahead.
Shop Now

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

Size 11 Medium Size Penny Keeper Shoes

58 items found

Filters

Search Results

. Cole Haan - Ledley Grand Penny Loafers. Color British Tan/Dark Natural. $309.95.

Red Cole Haan Ledley Grand Penny Loafers

Red Cole Haan Ledley Grand Penny Loafers

+2

Brand Name: Cole Haan
Product Name: Ledley Grand Penny Loafers
Gender: Men's
Color: British Tan/Dark Natural
Price: $309.95
Rating

Globe - Liaizon. Color Dark Brown. Low Stock. $119.95. 5.0 out of 5 stars

Low Stock

Brown Globe Liaizon

Brown Globe Liaizon

Brand Name: Globe
Product Name: Liaizon
Gender: Men's
Color: Dark Brown
Price: $119.95
Rating: 5Rated 5 stars out of 5(3)

Florsheim - Throttle Penny. Color Brown Crazy Horse II. On sale for $79.95. MSRP $110.00. 27% off. 4.2 out of 5 stars

Brown Florsheim Throttle Penny

Brown Florsheim Throttle Penny

+2

Brand Name: Florsheim
Product Name: Throttle Penny
Gender: Men's
Color: Brown Crazy Horse II
Price: $79.95MSRP: $11027% OFF
Rating: 4Rated 4 stars out of 5(25)

Frye - Tyler Flex Penny. Color Midnight. $198.00. 4.0 out of 5 stars

Navy Frye Tyler Flex Penny

Navy Frye Tyler Flex Penny

+5

Brand Name: Frye
Product Name: Tyler Flex Penny
Gender: Men's
Color: Midnight
Price: $198
Rating: 4Rated 4 stars out of 5(10)

Rockport - Classic Loafer Lite Penny. Color Dark Brown. On sale for $89.95. MSRP $124.95. 28% off. 3.9 out of 5 stars

Brown Rockport Classic Loafer Lite Penny

Brown Rockport Classic Loafer Lite Penny

+3

Brand Name: Rockport
Product Name: Classic Loafer Lite Penny
Gender: Men's
Color: Dark Brown
Price: $89.95MSRP: $124.9528% OFF
Rating: 4Rated 4 stars out of 5(417)

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(64)

Dockers - Colleague. Color Cordovan. On sale for $59.94. MSRP $90.00. 33% off. 4.2 out of 5 stars

Burgundy Dockers Colleague

Burgundy Dockers Colleague

+3

Brand Name: Dockers
Product Name: Colleague
Gender: Men's
Color: Cordovan
Price: $59.94MSRP: $9033% OFF
Rating: 4Rated 4 stars out of 5(6)

Florsheim - Berkley Flex Penny Loafers. Color Black/Brown. $140.00. 4.1 out of 5 stars

Black Florsheim Berkley Flex Penny Loafers

Black Florsheim Berkley Flex Penny Loafers

+5

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

Marc Joseph New York - Nebraska. Color Black Grainy. On sale for $89.95. MSRP $185.00. 51% off. 4.1 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 Grainy
Price: $89.95MSRP: $18551% OFF
Rating: 4Rated 4 stars out of 5(20)

Johnston & Murphy - Hayes Penny Loafers. Color Burgundy. $129.85. 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: $129.85
Rating: 4Rated 4 stars out of 5(117)

Nunn Bush - Drexel Moc Toe Penny Loafer with KORE Walking Comfort Technology. Color Cognac. On sale for $79.95. MSRP $110.00. 27% off. 4.3 out of 5 stars

Tan Nunn Bush Drexel Moc Toe Penny Loafer with KORE Walking Comfort Technology

Tan Nunn Bush Drexel Moc Toe Penny Loafer with KORE Walking Comfort Technology

+2

Brand Name: Nunn Bush
Product Name: Drexel Moc Toe Penny Loafer with KORE Walking Comfort Technology
Gender: Men's
Color: Cognac
Price: $79.95MSRP: $11027% OFF
Rating: 4Rated 4 stars out of 5(176)

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: $10030% OFF
Rating: 4Rated 4 stars out of 5(331)

Marc Joseph New York - Monaco. Color Black Napa. Low Stock. On sale for $59.65. MSRP $185.00. 68% off. 4.0 out of 5 stars

Low Stock

Black Marc Joseph New York Monaco

Black Marc Joseph New York Monaco

+5

Brand Name: Marc Joseph New York
Product Name: Monaco
Gender: Men's
Color: Black Napa
Price: $59.65MSRP: $18568% OFF
Rating: 4Rated 4 stars out of 5(6)

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

Black Polo Ralph Lauren Alston Penny

Black Polo Ralph Lauren Alston Penny

+2

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

Cole Haan - Grand Laser Penny Driver. Color Black/Black. On sale for $75.00. MSRP $150.00. 50% off. 4.0 out of 5 stars

Black Cole Haan Grand Laser Penny Driver

Black Cole Haan Grand Laser Penny Driver

+2

Brand Name: Cole Haan
Product Name: Grand Laser Penny Driver
Gender: Men's
Color: Black/Black
Price: $75MSRP: $15050% OFF
Rating: 4Rated 4 stars out of 5(75)

Johnston & Murphy - Collier Penny Loafers. Color Denim Suede. $154.95.

Blue Johnston & Murphy Collier Penny Loafers

Blue Johnston & Murphy Collier Penny Loafers

Brand Name: Johnston & Murphy
Product Name: Collier Penny Loafers
Gender: Men's
Color: Denim Suede
Price: $154.95
Rating

Nunn Bush - Odin II Moc Toe Penny Loafer Lightweight and Comfortable Slip-On. Color Cognac. On sale for $79.95. MSRP $110.00. 27% off. 5.0 out of 5 stars

Tan Nunn Bush Odin II Moc Toe Penny Loafer Lightweight and Comfortable Slip-On

Tan Nunn Bush Odin II Moc Toe Penny Loafer Lightweight and Comfortable Slip-On

+3

Brand Name: Nunn Bush
Product Name: Odin II Moc Toe Penny Loafer Lightweight and Comfortable Slip-On
Gender: Men's
Color: Cognac
Price: $79.95MSRP: $11027% OFF
Rating: 5Rated 5 stars out of 5(5)

Marc Joseph New York - River Road. Color Black Grainy. On sale for $74.00. MSRP $185.00. 60% off. 5.0 out of 5 stars

Black Marc Joseph New York River Road

Black Marc Joseph New York River Road

+3

Brand Name: Marc Joseph New York
Product Name: River Road
Gender: Men's
Color: Black Grainy
Price: $74MSRP: $18560% OFF
Rating: 5Rated 5 stars out of 5(2)

Nunn Bush - Noah Beef Roll Penny Loafers. Color Black. On sale for $79.95. MSRP $110.00. 27% off. 4.1 out of 5 stars

Black Nunn Bush Noah Beef Roll Penny Loafers

Black Nunn Bush Noah Beef Roll Penny Loafers

+2

Brand Name: Nunn Bush
Product Name: Noah Beef Roll Penny Loafers
Gender: Men's
Color: Black
Price: $79.95MSRP: $11027% OFF
Rating: 4Rated 4 stars out of 5(67)

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

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(55)

To Boot New York - Keats. Color Black. $398.00.

Black To Boot New York Keats

Black To Boot New York Keats

+2

Brand Name: To Boot New York
Product Name: Keats
Gender: Men's
Color: Black
Price: $398
Rating

Tommy Hilfiger - Amile. Color Dark Brown. On sale for $59.63. MSRP $89.00. 33% off. 4.6 out of 5 stars

Brown Tommy Hilfiger Amile

Brown Tommy Hilfiger Amile

+4

Brand Name: Tommy Hilfiger
Product Name: Amile
Gender: Men's
Color: Dark Brown
Price: $59.63MSRP: $8933% OFF
Rating: 5Rated 5 stars out of 5(5)

Samuel Hubbard - Free Spirit for Him. Color Brown Leather. $195.00. 3.8 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(5)

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)

Cole Haan - American Classics Penny Loafers. Color Dark Chocolate/Light Amber Brushoff/Black. On sale for $156.38. MSRP $165.00. 5% off. 4.2 out of 5 stars

Mahogany Cole Haan American Classics Penny Loafers

Mahogany Cole Haan American Classics Penny Loafers

+1

Brand Name: Cole Haan
Product Name: American Classics Penny Loafers
Gender: Men's
Color: Dark Chocolate/Light Amber Brushoff/Black
Price: $156.38MSRP: $1655% OFF
Rating: 4Rated 4 stars out of 5(360)

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

Brown Andre Assous Mateo Loafers

Brown Andre Assous Mateo Loafers

+2

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

Tommy Hilfiger - Simol. Color Black. On sale for $65.40. MSRP $109.00. 40% off. 3.0 out of 5 stars

Black Tommy Hilfiger Simol

Black Tommy Hilfiger Simol

Brand Name: Tommy Hilfiger
Product Name: Simol
Gender: Men's
Color: Black
Price: $65.40MSRP: $10940% OFF
Rating: 3Rated 3 stars out of 5(2)

Bruno Magli - Lastra. Color Brown. Low Stock. $298.00. 5.0 out of 5 stars

Low Stock

Brown Bruno Magli Lastra

Brown Bruno Magli Lastra

+2

Brand Name: Bruno Magli
Product Name: Lastra
Gender: Men's
Color: Brown
Price: $298
Rating: 5Rated 5 stars out of 5(1)

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

Low Stock

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)

Bruno Magli - Raging Penny. Color Cognac. $395.00. 3.0 out of 5 stars

Tan Bruno Magli Raging Penny

Tan Bruno Magli Raging Penny

Brand Name: Bruno Magli
Product Name: Raging Penny
Gender: Men's
Color: Cognac
Price: $395
Rating: 3Rated 3 stars out of 5(3)

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

Red Allen Edmonds Supersport Penny

Red Allen Edmonds Supersport Penny

+2

Brand Name: Allen Edmonds
Product Name: Supersport Penny
Gender: Men's
Color: Dark Chili
Price: $300
Rating: 4Rated 4 stars out of 5(29)

To Boot New York - Ravello. Color Black. Low Stock. $425.00. 5.0 out of 5 stars

Low Stock

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: $425
Rating: 5Rated 5 stars out of 5(1)

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

Johnston & Murphy - Baldwin Driver Penny. Color Cognac. On sale for $218.00. MSRP $228.00. 4% off. 3.9 out of 5 stars

Tan Johnston & Murphy Baldwin Driver Penny

Tan Johnston & Murphy Baldwin Driver Penny

Brand Name: Johnston & Murphy
Product Name: Baldwin Driver Penny
Gender: Men's
Color: Cognac
Price: $218MSRP: $2284% OFF
Rating: 4Rated 4 stars out of 5(31)

Stacy Adams - Spencer Penny Slip-On. Color Tan. On sale for $97.50. MSRP $130.00. 25% off. 4.8 out of 5 stars

Tan Stacy Adams Spencer Penny Slip-On

Tan Stacy Adams Spencer Penny Slip-On

+2

Brand Name: Stacy Adams
Product Name: Spencer Penny Slip-On
Gender: Men's
Color: Tan
Price: $97.50MSRP: $13025% OFF
Rating: 5Rated 5 stars out of 5(9)

Allen Edmonds - Randolph 2.0 Slip-on Sneaker. Color Light Brown Suede. $350.00. 3.5 out of 5 stars

Brown Allen Edmonds Randolph 2.0 Slip-on Sneaker

Brown 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: Light Brown Suede
Price: $350
Rating: 4Rated 4 stars out of 5(2)

Calvin Klein - Olin. Color Dark Grey. $59.00.

Gray Calvin Klein Olin

Gray Calvin Klein Olin

+2

Brand Name: Calvin Klein
Product Name: Olin
Gender: Men's
Color: Dark Grey
Price: $59
Rating

COACH - Declan Loafer. Color Dark Saddle. $250.00. 4.8 out of 5 stars

Tan COACH Declan Loafer

Tan COACH Declan Loafer

Brand Name: COACH
Product Name: Declan Loafer
Gender: Men's
Color: Dark Saddle
Price: $250
Rating: 5Rated 5 stars out of 5(4)

Allen Edmonds - Randolph. Color Coffee. $450.00. 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: $450
Rating: 4Rated 4 stars out of 5(35)

Steve Madden - Santee. Color Black 1. On sale for $90.00. MSRP $120.00. 25% off.

Black Steve Madden Santee

Black Steve Madden Santee

Brand Name: Steve Madden
Product Name: Santee
Gender: Men's
Color: Black 1
Price: $90MSRP: $12025% OFF
Rating

Sperry - Cabo II Penny. Color Sand. Low Stock. On sale for $32.98. MSRP $109.95. 70% off. 3.9 out of 5 stars

Low Stock

Bone Sperry Cabo II Penny

Bone Sperry Cabo II Penny

Brand Name: Sperry
Product Name: Cabo II Penny
Gender: Men's
Color: Sand
Price: $32.98MSRP: $109.9570% OFF
Rating: 4Rated 4 stars out of 5(21)

Allen Edmonds - Randolph. Color Black Calf. $450.00. 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: $450
Rating: 3Rated 3 stars out of 5(11)

Magnanni - Vicente. Color Cognac. Low Stock. $835.00. 4.0 out of 5 stars

Low Stock

Tan Magnanni Vicente

Tan Magnanni Vicente

Brand Name: Magnanni
Product Name: Vicente
Gender: Men's
Color: Cognac
Price: $835
Rating: 4Rated 4 stars out of 5(1)

Steve Madden - Jules. Color Black/ Black. Low Stock. On sale for $90.00. MSRP $120.00. 25% off.

Low Stock

Black Steve Madden Jules

Black Steve Madden Jules

Brand Name: Steve Madden
Product Name: Jules
Gender: Men's
Color: Black/ Black
Price: $90MSRP: $12025% OFF
Rating

La Canadienne - Talbott. Color Champagne. $435.00.

Gold La Canadienne Talbott

Gold La Canadienne Talbott

Brand Name: La Canadienne
Product Name: Talbott
Gender: Men's
Color: Champagne
Price: $435
Rating

To Boot New York - Bennett. Color Cuoio. $398.00.

Brown To Boot New York Bennett

Brown To Boot New York Bennett

Brand Name: To Boot New York
Product Name: Bennett
Gender: Men's
Color: Cuoio
Price: $398
Rating

Taft - LF-Sterling-BRF. Color Brown Floral. $295.00.

Multi Taft LF-Sterling-BRF

Multi Taft LF-Sterling-BRF

Brand Name: Taft
Product Name: LF-Sterling-BRF
Gender: Men's
Color: Brown Floral
Price: $295
Rating

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

Black Marc Joseph New York Valley Road 2.0

Black Marc Joseph New York Valley Road 2.0

+2

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

Steve Madden - Ramsee. Color Blue Suede. $120.00. 3.8 out of 5 stars

Blue Steve Madden Ramsee

Blue Steve Madden Ramsee

+3

Brand Name: Steve Madden
Product Name: Ramsee
Gender: Men's
Color: Blue Suede
Price: $120
Rating: 4Rated 4 stars out of 5(10)

Cole Haan - Pinch Prep Penny Loafer. Color Black Brushoff. On sale for $129.95. MSRP $140.00. 7% off. 3.9 out of 5 stars

Black Cole Haan Pinch Prep Penny Loafer

Black Cole Haan Pinch Prep Penny Loafer

+5

Brand Name: Cole Haan
Product Name: Pinch Prep Penny Loafer
Gender: Men's
Color: Black Brushoff
Price: $129.95MSRP: $1407% OFF
Rating: 4Rated 4 stars out of 5(12)

Bruno Magli - Tonio. Color Black Cervo. On sale for $276.50. MSRP $395.00. 30% off. 5.0 out of 5 stars

Black Bruno Magli Tonio

Black Bruno Magli Tonio

+2 colors/patterns

Brand Name: Bruno Magli
Product Name: Tonio
Gender: Men's
Color: Black Cervo
Price: $276.50MSRP: $39530% OFF
Rating: 5Rated 5 stars out of 5(2)

Bruno Magli - Maioco Penny. Color Brown. Low Stock. $395.00.

Low Stock

Brown Bruno Magli Maioco Penny

Brown Bruno Magli Maioco Penny

+3

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

Tommy Hilfiger - Ruven. Color Black. On sale for $54.97. MSRP $95.00. 42% off. 5.0 out of 5 stars

Black Tommy Hilfiger Ruven

Black Tommy Hilfiger Ruven

+2

Brand Name: Tommy Hilfiger
Product Name: Ruven
Gender: Men's
Color: Black
Price: $54.97MSRP: $9542% OFF
Rating: 5Rated 5 stars out of 5(1)

Florsheim - Zaffiro Moc Toe Penny Loafers. Color Black. $144.99. 4.8 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(21)

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)

Cole Haan - Hawthorne Penny Loafer. Color Habana. On sale for $111.00. MSRP $148.00. 25% 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: $111MSRP: $14825% OFF
Rating: 4Rated 4 stars out of 5(7)

Marc Joseph New York - Union Street Perforated. Color Fast Blue Grainy. Low Stock. On sale for $87.50. MSRP $175.00. 50% off.

Low Stock

Blue Marc Joseph New York Union Street Perforated

Blue Marc Joseph New York Union Street Perforated

Brand Name: Marc Joseph New York
Product Name: Union Street Perforated
Gender: Men's
Color: Fast Blue Grainy
Price: $87.50MSRP: $17550% OFF
Rating

Rockport - Liam. Color Dark Brown Leather. On sale for $64.97. MSRP $129.95. 50% off. 4.3 out of 5 stars

Brown Rockport Liam

Brown Rockport Liam

Brand Name: Rockport
Product Name: Liam
Gender: Men's
Color: Dark Brown Leather
Price: $64.97MSRP: $129.9550% OFF
Rating: 4Rated 4 stars out of 5(3)

Join Our Email List

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

*One code per email address.