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

Size 8 Penny Keeper Leather Loafers

50 items found

Sort By

Your Selections

Search Results

Florsheim - Throttle Penny. Color Black II. On sale for $79.95. MSRP $110.00. 27% off. 3.9 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: $110.0027% OFF
Rating: 4Rated 4 stars out of 5(18)

Marc Joseph New York - Monaco. Color Brown Grainy. On sale for $59.45. MSRP $185.00. 68% off. 3.5 out of 5 stars

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 Grainy
Price: $59.45MSRP: $185.0068% OFF
Rating: 4Rated 4 stars out of 5(2)

Marc Joseph New York - Nebraska. Color Grey Suede. On sale for $89.95. MSRP $185.00. 51% off. 3.8 out of 5 stars

Gray Marc Joseph New York Nebraska

Gray Marc Joseph New York Nebraska

+8

Brand Name: Marc Joseph New York
Product Name: Nebraska
Gender: Men's
Color: Grey Suede
Price: $89.95MSRP: $185.0051% OFF
Rating: 4Rated 4 stars out of 5(13)

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(409)

Frye - Tyler Flex Penny. Color Mushroom. On sale for $158.40. MSRP $198.00. 20% off. 4.2 out of 5 stars

Gray Frye Tyler Flex Penny

Gray Frye Tyler Flex Penny

+5

Brand Name: Frye
Product Name: Tyler Flex Penny
Gender: Men's
Color: Mushroom
Price: $158.40MSRP: $198.0020% OFF
Rating: 4Rated 4 stars out of 5(4)

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: $110.0027% OFF
Rating: 4Rated 4 stars out of 5(172)

Nunn Bush - Odin II Moc Toe Penny Loafer Lightweight and Comfortable Slip-On. Color Black/Brown. On sale for $98.95. MSRP $109.95. 10% off.

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

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

Brand Name: Nunn Bush
Product Name: Odin II Moc Toe Penny Loafer Lightweight and Comfortable Slip-On
Gender: Men's
Color: Black/Brown
Price: $98.95MSRP: $109.9510% OFF
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: $100.0030% OFF
Rating: 4Rated 4 stars out of 5(318)

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

Neutral Florsheim Sorrento Moc Toe Penny Loafer

Neutral Florsheim Sorrento Moc Toe Penny Loafer

+2

Brand Name: Florsheim
Product Name: Sorrento Moc Toe Penny Loafer
Gender: Men's
Color: Cognac Smooth
Price: $109.95MSRP: $145.0024% OFF
Rating: 4Rated 4 stars out of 5(45)

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

Burgundy Johnston & Murphy Hayes Penny Loafer

Burgundy Johnston & Murphy Hayes Penny Loafer

+2

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

Cole Haan - Pinch Weekender Penny Textured. Color Dark Chocolate Pebble/Ivory. On sale for $83.20. MSRP $100.00. 17% off. 4.6 out of 5 stars

Black Cole Haan Pinch Weekender Penny Textured

Black Cole Haan Pinch Weekender Penny Textured

+4

Brand Name: Cole Haan
Product Name: Pinch Weekender Penny Textured
Gender: Men's
Color: Dark Chocolate Pebble/Ivory
Price: $83.20MSRP: $100.0017% OFF
Rating: 5Rated 5 stars out of 5(5)

Florsheim - Berkley Flex Penny Loafer. Color Black/Brown. $140.00. 4.2 out of 5 stars

Black Florsheim Berkley Flex Penny Loafer

Black Florsheim Berkley Flex Penny Loafer

+5

Brand Name: Florsheim
Product Name: Berkley Flex Penny Loafer
Gender: Men's
Color: Black/Brown
Price: $140.00
Rating: 4Rated 4 stars out of 5(202)

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

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)

Nunn Bush - Noah Beef Roll Penny Loafer. 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 Loafer

Black Nunn Bush Noah Beef Roll Penny Loafer

+2

Brand Name: Nunn Bush
Product Name: Noah Beef Roll Penny Loafer
Gender: Men's
Color: Black
Price: $79.95MSRP: $110.0027% OFF
Rating: 4Rated 4 stars out of 5(67)

Stacy Adams - Spencer Penny Slip-On. Color Tan. On sale for $108.81. MSRP $130.00. 16% off. 4.8 out of 5 stars

Tan Stacy Adams Spencer Penny Slip-On

Tan Stacy Adams Spencer Penny Slip-On

+4

Brand Name: Stacy Adams
Product Name: Spencer Penny Slip-On
Gender: Men's
Color: Tan
Price: $108.81MSRP: $130.0016% OFF
Rating: 5Rated 5 stars out of 5(8)

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

Tan ECCO S Lite Moc Penny Loafer

Tan ECCO S Lite Moc Penny Loafer

+2

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

To Boot New York - Moore. Color Brown. Low Stock. On sale for $179.55. MSRP $399.00. 55% off. 4.3 out of 5 stars

Low Stock

Brown To Boot New York Moore

Brown To Boot New York Moore

+3

Brand Name: To Boot New York
Product Name: Moore
Gender: Men's
Color: Brown
Price: $179.55MSRP: $399.0055% OFF
Rating: 4Rated 4 stars out of 5(3)

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

Rockport - Liam. Color Dark Natural Leather. On sale for $84.46. MSRP $129.95. 35% off. 4.0 out of 5 stars

Brown Rockport Liam

Brown Rockport Liam

+1

Brand Name: Rockport
Product Name: Liam
Gender: Men's
Color: Dark Natural Leather
Price: $84.46MSRP: $129.9535% OFF
Rating: 4Rated 4 stars out of 5(2)

Bruno Magli - Maioco Penny. Color Brown. Low Stock. On sale for $279.97. MSRP $395.00. 29% off.

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: $279.97MSRP: $395.0029% OFF
Rating

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

Low Stock

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: $300.00
Rating: 4Rated 4 stars out of 5(29)

Bruno Magli - Tonio. Color Black 2. Low Stock. On sale for $337.50. MSRP $375.00. 10% off. 5.0 out of 5 stars

Low Stock

Black Bruno Magli Tonio

Black Bruno Magli Tonio

Brand Name: Bruno Magli
Product Name: Tonio
Gender: Men's
Color: Black 2
Price: $337.50MSRP: $375.0010% OFF
Rating: 5Rated 5 stars out of 5(2)

Johnston & Murphy - Dayton Woven Penny. Color Brown Italian Calfskin. On sale for $196.00. MSRP $245.00. 20% 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: $196.00MSRP: $245.0020% OFF
Rating: 4Rated 4 stars out of 5(15)

Marc Joseph New York - Union Street 2. Color Olive Suede. On sale for $124.00. MSRP $155.00. 20% off. 4.8 out of 5 stars

Olive Marc Joseph New York Union Street 2

Olive Marc Joseph New York Union Street 2

+3

Brand Name: Marc Joseph New York
Product Name: Union Street 2
Gender: Men's
Color: Olive Suede
Price: $124.00MSRP: $155.0020% OFF
Rating: 5Rated 5 stars out of 5(4)

Bruno Magli - Raging Penny. Color Cognac. $395.00. 5.0 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: $395.00
Rating: 5Rated 5 stars out of 5(1)

Florsheim - Zaffiro Moc Toe Penny Loafer. Color Black. $145.00. 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: $145.00
Rating: 5Rated 5 stars out of 5(16)

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

Black Samuel Hubbard Free Spirit for Him

Black Samuel Hubbard Free Spirit for Him

+2

Brand Name: Samuel Hubbard
Product Name: Free Spirit for Him
Gender: Men's
Color: Black Tumbled Leather
Price: $195.00
Rating: 4Rated 4 stars out of 5(4)

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: $350.00
Rating: 4Rated 4 stars out of 5(2)

Marc Joseph New York - Union Street Perforated. Color Fast Blue Grainy. $175.00.

Blue Marc Joseph New York Union Street Perforated

Blue Marc Joseph New York Union Street Perforated

+2

Brand Name: Marc Joseph New York
Product Name: Union Street Perforated
Gender: Men's
Color: Fast Blue Grainy
Price: $175.00
Rating

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 - 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: $450.00
Rating: 4Rated 4 stars out of 5(35)

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

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: $399.00MSRP: $425.006% OFF
Rating

Anthony Veer - Sherman Penny Loafer. Color Honey Brown. Low Stock. On sale for $110.45. MSRP $164.95. 33% 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: Honey Brown
Price: $110.45MSRP: $164.9533% OFF
Rating: 4Rated 4 stars out of 5(101)

Martin Dingman - Bill Penny. Color Chestnut. $250.00.

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: $250.00
Rating

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)

Steve Madden - Jules. Color Black/ Black. On sale for $100.30. MSRP $120.00. 16% off.

Black Steve Madden Jules

Black Steve Madden Jules

Brand Name: Steve Madden
Product Name: Jules
Gender: Men's
Color: Black/ Black
Price: $100.30MSRP: $120.0016% 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(1)

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: $450.00
Rating: 3Rated 3 stars out of 5(11)

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

Black Johnston & Murphy Baldwin Penny

Black Johnston & Murphy Baldwin Penny

+5

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

Cole Haan - Pinch Prep Penny Loafer. Color Burgundy Box Brush Off/Black. Low Stock. $139.68. 3.9 out of 5 stars

Low Stock

Burgundy Cole Haan Pinch Prep Penny Loafer

Burgundy Cole Haan Pinch Prep Penny Loafer

+6

Brand Name: Cole Haan
Product Name: Pinch Prep Penny Loafer
Gender: Men's
Color: Burgundy Box Brush Off/Black
Price: $139.68
Rating: 4Rated 4 stars out of 5(9)

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)

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)

Cole Haan - American Classics Penny Loafer. Color Dark Chocolate/Light Amber Brushoff/Black. On sale for $154.27. MSRP $165.00. 7% off. 4.2 out of 5 stars

Mahogany Cole Haan American Classics Penny Loafer

Mahogany Cole Haan American Classics Penny Loafer

+1

Brand Name: Cole Haan
Product Name: American Classics Penny Loafer
Gender: Men's
Color: Dark Chocolate/Light Amber Brushoff/Black
Price: $154.27MSRP: $165.007% OFF
Rating: 4Rated 4 stars out of 5(359)

Cole Haan - Grand Laser Penny Driver. Color Black/Black. On sale for $108.98. MSRP $150.00. 27% off. 3.9 out of 5 stars

Black Cole Haan Grand Laser Penny Driver

Black Cole Haan Grand Laser Penny Driver

+4

Brand Name: Cole Haan
Product Name: Grand Laser Penny Driver
Gender: Men's
Color: Black/Black
Price: $108.98MSRP: $150.0027% OFF
Rating: 4Rated 4 stars out of 5(73)

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

+3

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

Bruno Magli - Lastra. Color Brown. $298.00.

Brown Bruno Magli Lastra

Brown Bruno Magli Lastra

+2

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

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: $140.00
Rating: 4Rated 4 stars out of 5(282)

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)

Cole Haan - Hawthorne Penny Loafer. Color Black. On sale for $133.20. MSRP $148.00. 10% off. 3.5 out of 5 stars

Black Cole Haan Hawthorne Penny Loafer

Black Cole Haan Hawthorne Penny Loafer

+2

Brand Name: Cole Haan
Product Name: Hawthorne Penny Loafer
Gender: Men's
Color: Black
Price: $133.20MSRP: $148.0010% OFF
Rating: 4Rated 4 stars out of 5(4)

Johnston & Murphy - Dayton Penny Loafer. Color Brown. On sale for $196.00. MSRP $245.00. 20% 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: $196.00MSRP: $245.0020% OFF
Rating: 5Rated 5 stars out of 5(7)

Join Our List, Get 10% Off

Sign up for Zappos emails—new subscribers get 10% off a future order!* Plus, get early access to sales, coupons, and more. (One code per email address.)