GOING FAST
EXTRA 20% OFF*
Save on select styles with code EXTRA20
Shop Now
*Exclusions apply

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

Size 10 Penny Keeper Round Toe Products

41 items found

Filters

Search Results

Florsheim - Throttle Penny. Color Black II. On sale for $79.95. MSRP $110.00. 27% off. 4.1 out of 5 stars

Black Florsheim Throttle Penny

Black Florsheim Throttle Penny

+2

Brand Name: Florsheim
Product Name: Throttle Penny
Gender: Men's
Color: Black II
Price: $79.95MSRP: $11027% OFF
Rating: 4Rated 4 stars out of 5(23)

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

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)

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

Tan Rockport Classic Loafer Lite Penny

Tan Rockport Classic Loafer Lite Penny

+3

Brand Name: Rockport
Product Name: Classic Loafer Lite Penny
Gender: Men's
Color: Cognac
Price: $89.95MSRP: $124.9528% OFF
Rating: 4Rated 4 stars out of 5(415)

Dockers - Colleague. Color Tan. On sale for $59.94. MSRP $90.00. 33% off. 4.0 out of 5 stars

Tan Dockers Colleague

Tan Dockers Colleague

+3

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

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)

Johnston & Murphy - Hayes Penny Loafers. Color Black. $129.85. 4.1 out of 5 stars

Black Johnston & Murphy Hayes Penny Loafers

Black Johnston & Murphy Hayes Penny Loafers

+2

Brand Name: Johnston & Murphy
Product Name: Hayes Penny Loafers
Gender: Men's
Color: Black
Price: $129.85
Rating: 4Rated 4 stars out of 5(117)

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(74)

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)

Nunn Bush - Drexel Moc Toe Penny Loafer with KORE Walking Comfort Technology. Color Cognac. On sale for $69.99. MSRP $110.00. 36% 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: $69.99MSRP: $11036% OFF
Rating: 4Rated 4 stars out of 5(174)

Marc Joseph New York - Monaco. Color Brown Napa. Low Stock. On sale for $69.95. MSRP $185.00. 62% off. 3.5 out of 5 stars

Low Stock

Brown Marc Joseph New York Monaco

Brown Marc Joseph New York Monaco

+5

Brand Name: Marc Joseph New York
Product Name: Monaco
Gender: Men's
Color: Brown Napa
Price: $69.95MSRP: $18562% OFF
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: $10030% OFF
Rating: 4Rated 4 stars out of 5(329)

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 Olive Waxed English Suede/Brown Full Grain. $217.95. 4.4 out of 5 stars

Olive Johnston & Murphy Baldwin Penny

Olive Johnston & Murphy Baldwin Penny

+7

Brand Name: Johnston & Murphy
Product Name: Baldwin Penny
Gender: Men's
Color: Olive Waxed English Suede/Brown Full Grain
Price: $217.95
Rating: 4Rated 4 stars out of 5(52)

Bruno Magli - Lastra. Color Black. $298.00. 5.0 out of 5 stars

Black Bruno Magli Lastra

Black Bruno Magli Lastra

+2

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

To Boot New York - Alek. Color Moro. Low Stock. On sale for $249.95. MSRP $425.00. 41% off. 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: $249.95MSRP: $42541% OFF
Rating: 4Rated 4 stars out of 5(3)

Johnston & Murphy - Emmett Penny. Color Dark Tan Full Grain. $119.90. 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: $119.90
Rating: 5Rated 5 stars out of 5(70)

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)

Cole Haan - Wyatt Penny Driver. Color Black/Black. On sale for $115.97. MSRP $140.00. 17% off. 4.3 out of 5 stars

Black Cole Haan Wyatt Penny Driver

Black Cole Haan Wyatt Penny Driver

+2

Brand Name: Cole Haan
Product Name: Wyatt Penny Driver
Gender: Men's
Color: Black/Black
Price: $115.97MSRP: $14017% OFF
Rating: 4Rated 4 stars out of 5(283)

Bruno Magli - Raging Penny. Color Black. $395.00. 3.0 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
Rating: 3Rated 3 stars out of 5(3)

Cole Haan - Pinch Prep Penny Loafer. Color Scotch. On sale for $118.01. MSRP $140.00. 16% off. 3.9 out of 5 stars

Brown Cole Haan Pinch Prep Penny Loafer

Brown Cole Haan Pinch Prep Penny Loafer

+4

Brand Name: Cole Haan
Product Name: Pinch Prep Penny Loafer
Gender: Men's
Color: Scotch
Price: $118.01MSRP: $14016% OFF
Rating: 4Rated 4 stars out of 5(12)

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

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)

. 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

Steve Madden - Crescent. Color Black Velvet. On sale for $69.97. MSRP $100.00. 30% off. 5.0 out of 5 stars

Black Steve Madden Crescent

Black Steve Madden Crescent

Brand Name: Steve Madden
Product Name: Crescent
Gender: Men's
Color: Black Velvet
Price: $69.97MSRP: $10030% OFF
Rating: 5Rated 5 stars out of 5(1)

Cole Haan - American Classics Penny Loafers. Color Deep Burundy/Black. $165.00. 4.2 out of 5 stars

Burgundy Cole Haan American Classics Penny Loafers

Burgundy Cole Haan American Classics Penny Loafers

+1

Brand Name: Cole Haan
Product Name: American Classics Penny Loafers
Gender: Men's
Color: Deep Burundy/Black
Price: $165
Rating: 4Rated 4 stars out of 5(360)

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)

Allen Edmonds - Randolph 2.0 Slip-on Sneaker. Color Walnut Leather. $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: Walnut Leather
Price: $350
Rating: 4Rated 4 stars out of 5(2)

Tommy Hilfiger - Ladden. Color Tan. Low Stock. On sale for $59.99. MSRP $99.00. 39% off.

Low Stock

Tan Tommy Hilfiger Ladden

Tan Tommy Hilfiger Ladden

Brand Name: Tommy Hilfiger
Product Name: Ladden
Gender: Men's
Color: Tan
Price: $59.99MSRP: $9939% 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

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)

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

Steve Madden - Jules. Color Black/ Black. Low Stock. On sale for $108.00. MSRP $120.00. 10% 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: $108MSRP: $12010% OFF
Rating

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

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)

. 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

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

Taupe Steve Madden Ramsee

Taupe Steve Madden Ramsee

+3

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

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)

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 - Hawthorne Penny Loafer. Color Habana. On sale for $136.01. MSRP $148.00. 8% 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: $136.01MSRP: $1488% OFF
Rating: 4Rated 4 stars out of 5(7)

To Boot New York - Ravello. Color Black. Low Stock. On sale for $399.00. MSRP $425.00. 6% off. 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: $399MSRP: $4256% OFF
Rating: 5Rated 5 stars out of 5(1)

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)

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)

Join Our Email List

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

*One code per email address.