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

Size 9 M Size Penny Keeper Shoes

46 items found

Sort By

Your Selections

Search Results

Rockport - Classic Loafer Lite Penny. Color Black II. On sale for $79.95. MSRP $115.00. 30% off. 3.9 out of 5 stars

Black Rockport Classic Loafer Lite Penny

Black Rockport Classic Loafer Lite Penny

+3

Brand Name: Rockport
Product Name: Classic Loafer Lite Penny
Gender: Men's
Color: Black II
Price: $79.95MSRP: $115.0030% OFF
Rating: 4Rated 4 stars out of 5(408)

Marc Joseph New York - Nebraska. Color Tan Napa. On sale for $79.95. MSRP $185.00. 57% off. 4.6 out of 5 stars

Tan Marc Joseph New York Nebraska

Tan Marc Joseph New York Nebraska

+9

Brand Name: Marc Joseph New York
Product Name: Nebraska
Gender: Men's
Color: Tan Napa
Price: $79.95MSRP: $185.0057% OFF
Rating: 5Rated 5 stars out of 5(9)

Florsheim - Berkley Flex Penny Loafer. Color Brown Crazy Horse. On sale for $108.29. MSRP $125.00. 13% off. 4.2 out of 5 stars

Brown Florsheim Berkley Flex Penny Loafer

Brown Florsheim Berkley Flex Penny Loafer

+5

Brand Name: Florsheim
Product Name: Berkley Flex Penny Loafer
Gender: Men's
Color: Brown Crazy Horse
Price: $108.29MSRP: $125.0013% OFF
Rating: 4Rated 4 stars out of 5(194)

Cole Haan - Wyatt Penny Driver. Color British Tan/Nicotine. On sale for $112.00. MSRP $115.00. 3% 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: $115.003% OFF
Rating: 4Rated 4 stars out of 5(282)

Cole Haan - Grand Laser Penny Driver. Color British Tan/Java. On sale for $109.95. MSRP $140.00. 21% off. 3.9 out of 5 stars

Beige Cole Haan Grand Laser Penny Driver

Beige Cole Haan Grand Laser Penny Driver

+5

Brand Name: Cole Haan
Product Name: Grand Laser Penny Driver
Gender: Men's
Color: British Tan/Java
Price: $109.95MSRP: $140.0021% OFF
Rating: 4Rated 4 stars out of 5(72)

Cole Haan - American Classics Penny Loafer. Color Black/Black. $158.00. 4.2 out of 5 stars

Black Cole Haan American Classics Penny Loafer

Black Cole Haan American Classics Penny Loafer

+2

Brand Name: Cole Haan
Product Name: American Classics Penny Loafer
Gender: Men's
Color: Black/Black
Price: $158.00
Rating: 4Rated 4 stars out of 5(359)

Johnston & Murphy Collection - Baldwin Penny. Color Brandy. $195.00. 4.4 out of 5 stars

Brown Johnston & Murphy Collection Baldwin Penny

Brown Johnston & Murphy Collection Baldwin Penny

+6

Brand Name: Johnston & Murphy Collection
Product Name: Baldwin Penny
Gender: Men's
Color: Brandy
Price: $195.00
Rating: 4Rated 4 stars out of 5(51)

Nunn Bush - Drexel Moc Toe Penny Loafer with KORE Walking Comfort Technology. Color Cognac. On sale for $69.99. MSRP $100.00. 30% 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: $100.0030% OFF
Rating: 4Rated 4 stars out of 5(169)

Florsheim - Throttle Penny. Color Brown Crazy Horse II. On sale for $79.95. MSRP $110.00. 27% off. 4.3 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: $110.0027% OFF
Rating: 4Rated 4 stars out of 5(16)

Florsheim - Midtown Penny Slip-On. Color Cognac Smooth. On sale for $89.95. MSRP $125.00. 28% 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: $89.95MSRP: $125.0028% OFF
Rating: 4Rated 4 stars out of 5(112)

Nunn Bush - Lincoln Penny Loafer. Color Black Polished. On sale for $69.95. MSRP $95.00. 26% 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: $95.0026% OFF
Rating: 4Rated 4 stars out of 5(313)

Anthony Veer - Sherman Penny Loafer. Color Honey Brown. Low Stock. On sale for $108.72. MSRP $164.95. 34% 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: $108.72MSRP: $164.9534% OFF
Rating: 4Rated 4 stars out of 5(101)

Johnston & Murphy - Hayes Penny Loafer. Color Black. On sale for $99.90. MSRP $135.00. 26% off. 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: $99.90MSRP: $135.0026% OFF
Rating: 4Rated 4 stars out of 5(116)

Nunn Bush - Noah Beef Roll Penny Loafer. Color Brown. On sale for $79.95. MSRP $100.00. 20% off. 4.1 out of 5 stars

Brown Nunn Bush Noah Beef Roll Penny Loafer

Brown Nunn Bush Noah Beef Roll Penny Loafer

+2

Brand Name: Nunn Bush
Product Name: Noah Beef Roll Penny Loafer
Gender: Men's
Color: Brown
Price: $79.95MSRP: $100.0020% OFF
Rating: 4Rated 4 stars out of 5(67)

Cole Haan - Pinch Prep Penny Loafer. Color Black/Black. On sale for $119.99. MSRP $130.00. 8% off. 4.1 out of 5 stars

Black Cole Haan Pinch Prep Penny Loafer

Black Cole Haan Pinch Prep Penny Loafer

+7

Brand Name: Cole Haan
Product Name: Pinch Prep Penny Loafer
Gender: Men's
Color: Black/Black
Price: $119.99MSRP: $130.008% OFF
Rating: 4Rated 4 stars out of 5(8)

Florsheim - Zaffiro Moc Toe Penny Loafer. Color Cognac. On sale for $119.99. MSRP $130.00. 8% off. 4.7 out of 5 stars

Tan Florsheim Zaffiro Moc Toe Penny Loafer

Tan Florsheim Zaffiro Moc Toe Penny Loafer

+2

Brand Name: Florsheim
Product Name: Zaffiro Moc Toe Penny Loafer
Gender: Men's
Color: Cognac
Price: $119.99MSRP: $130.008% OFF
Rating: 5Rated 5 stars out of 5(16)

Florsheim - Sorrento Moc Toe Penny Loafer. Color Black Smooth. $129.95. 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: $129.95
Rating: 4Rated 4 stars out of 5(44)

Tommy Hilfiger - Amile. Color Taupe. On sale for $59.50. MSRP $85.00. 30% off. 4.6 out of 5 stars

Taupe Tommy Hilfiger Amile

Taupe Tommy Hilfiger Amile

+4

Brand Name: Tommy Hilfiger
Product Name: Amile
Gender: Men's
Color: Taupe
Price: $59.50MSRP: $85.0030% OFF
Rating: 5Rated 5 stars out of 5(5)

Cole Haan - Nanctucket Penny Loafer. Color Black Pebbled Leather/Ivory. $80.00. 4.5 out of 5 stars

Black Cole Haan Nanctucket Penny Loafer

Black Cole Haan Nanctucket Penny Loafer

+4

Brand Name: Cole Haan
Product Name: Nanctucket Penny Loafer
Gender: Men's
Color: Black Pebbled Leather/Ivory
Price: $80.00
Rating: 5Rated 5 stars out of 5(4)

Marc Joseph New York - Lexington. Color Brown Suede. Low Stock. On sale for $154.05. MSRP $195.00. 21% off. 4.3 out of 5 stars

Low Stock

Brown Marc Joseph New York Lexington

Brown Marc Joseph New York Lexington

Brand Name: Marc Joseph New York
Product Name: Lexington
Gender: Men's
Color: Brown Suede
Price: $154.05MSRP: $195.0021% OFF
Rating: 4Rated 4 stars out of 5(6)

Johnston & Murphy Collection - Baldwin Driver Penny. Color Black. On sale for $175.75. MSRP $185.00. 5% off. 3.9 out of 5 stars

Black Johnston & Murphy Collection Baldwin Driver Penny

Black Johnston & Murphy Collection Baldwin Driver Penny

+3

Brand Name: Johnston & Murphy Collection
Product Name: Baldwin Driver Penny
Gender: Men's
Color: Black
Price: $175.75MSRP: $185.005% OFF
Rating: 4Rated 4 stars out of 5(31)

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

Brown Marc Joseph New York Union Street 2

Brown Marc Joseph New York Union Street 2

+3

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

Marc Joseph New York - Valley Road 2.0. Color Navy Napa. On sale for $79.95. MSRP $195.00. 59% off. 4.2 out of 5 stars

Blue Marc Joseph New York Valley Road 2.0

Blue 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: Navy Napa
Price: $79.95MSRP: $195.0059% OFF
Rating: 4Rated 4 stars out of 5(9)

Stacy Adams - Spencer Penny Slip-On. Color Burgundy. On sale for $97.66. MSRP $120.00. 19% off. 5.0 out of 5 stars

Burgundy Stacy Adams Spencer Penny Slip-On

Burgundy Stacy Adams Spencer Penny Slip-On

+4

Brand Name: Stacy Adams
Product Name: Spencer Penny Slip-On
Gender: Men's
Color: Burgundy
Price: $97.66MSRP: $120.0019% OFF
Rating: 5Rated 5 stars out of 5(4)

Steve Madden - Ramsee. Color Taupe Suede. On sale for $51.60. MSRP $120.00. 57% off. 3.8 out of 5 stars

Taupe Steve Madden Ramsee

Taupe Steve Madden Ramsee

+2

Brand Name: Steve Madden
Product Name: Ramsee
Gender: Men's
Color: Taupe Suede
Price: $51.60MSRP: $120.0057% OFF
Rating: 4Rated 4 stars out of 5(10)

COACH - Declan Loafer. Color Midnight Navy. On sale for $187.50. MSRP $250.00. 25% off. 4.8 out of 5 stars

Blue COACH Declan Loafer

Blue COACH Declan Loafer

Brand Name: COACH
Product Name: Declan Loafer
Gender: Men's
Color: Midnight Navy
Price: $187.50MSRP: $250.0025% OFF
Rating: 5Rated 5 stars out of 5(4)

Polo Ralph Lauren - Alston Penny. Color Tan. On sale for $124.60. MSRP $178.00. 30% off. 3.0 out of 5 stars

Tan Polo Ralph Lauren Alston Penny

Tan Polo Ralph Lauren Alston Penny

+6

Brand Name: Polo Ralph Lauren
Product Name: Alston Penny
Gender: Men's
Color: Tan
Price: $124.60MSRP: $178.0030% OFF
Rating: 3Rated 3 stars out of 5(1)

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)

Frye - Tyler Flex Penny. Color Caramel. $198.00. 3.5 out of 5 stars

Brown Frye Tyler Flex Penny

Brown Frye Tyler Flex Penny

+4

Brand Name: Frye
Product Name: Tyler Flex Penny
Gender: Men's
Color: Caramel
Price: $198.00
Rating: 4Rated 4 stars out of 5(2)

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)

Rockport - Liam. Color Dark Brown Leather. On sale for $116.95. MSRP $129.95. 10% 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 Brown Leather
Price: $116.95MSRP: $129.9510% OFF
Rating: 4Rated 4 stars out of 5(2)

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)

Dockers - Colleague. Color Tan. On sale for $49.95. MSRP $79.00. 37% off. 3.3 out of 5 stars

Tan Dockers Colleague

Tan Dockers Colleague

+3

Brand Name: Dockers
Product Name: Colleague
Gender: Men's
Color: Tan
Price: $49.95MSRP: $79.0037% OFF
Rating: 3Rated 3 stars out of 5(3)

Bruno Magli - Silas. Color Taupe. Low Stock. On sale for $199.99. MSRP $298.00. 33% off. 3.1 out of 5 stars

Low Stock

Taupe Bruno Magli Silas

Taupe Bruno Magli Silas

Brand Name: Bruno Magli
Product Name: Silas
Gender: Men's
Color: Taupe
Price: $199.99MSRP: $298.0033% OFF
Rating: 3Rated 3 stars out of 5(7)

Cole Haan - Hawthorne Penny Loafer. Color Habana. $112.00. 3.5 out of 5 stars

Brown Cole Haan Hawthorne Penny Loafer

Brown Cole Haan Hawthorne Penny Loafer

+2

Brand Name: Cole Haan
Product Name: Hawthorne Penny Loafer
Gender: Men's
Color: Habana
Price: $112.00
Rating: 4Rated 4 stars out of 5(4)

Polo Ralph Lauren - Anders Penny. Color Brown. On sale for $117.60. MSRP $168.00. 30% off. 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: $117.60MSRP: $168.0030% OFF
Rating: 3Rated 3 stars out of 5(2)

SAS - Woodlawn. Color Mahogany. Low Stock. On sale for $166.81. MSRP $234.95. 29% off. 3.0 out of 5 stars

Low Stock

Mahogany SAS Woodlawn

Mahogany SAS Woodlawn

Brand Name: SAS
Product Name: Woodlawn
Gender: Men's
Color: Mahogany
Price: $166.81MSRP: $234.9529% OFF
Rating: 3Rated 3 stars out of 5(6)

Born - Simon III. Color Tan Full Grain. $119.95. 3.3 out of 5 stars

Tan Born Simon III

Tan Born Simon III

Brand Name: Born
Product Name: Simon III
Gender: Men's
Color: Tan Full Grain
Price: $119.95
Rating: 3Rated 3 stars out of 5(3)

Tommy Hilfiger - Simol. Color Cognac. Low Stock. On sale for $69.30. MSRP $99.00. 30% off. 3.0 out of 5 stars

Low Stock

Tan Tommy Hilfiger Simol

Tan Tommy Hilfiger Simol

Brand Name: Tommy Hilfiger
Product Name: Simol
Gender: Men's
Color: Cognac
Price: $69.30MSRP: $99.0030% OFF
Rating: 3Rated 3 stars out of 5(2)

Dockers - Colleague. Color Cordovan. On sale for $50.29. MSRP $70.00. 28% off. 2.0 out of 5 stars

Burgundy Dockers Colleague

Burgundy Dockers Colleague

Brand Name: Dockers
Product Name: Colleague
Gender: Men's
Color: Cordovan
Price: $50.29MSRP: $70.0028% OFF
Rating: 2Rated 2 stars out of 5(1)

Marc Joseph New York - Monaco. Color Cognac Grainy. On sale for $60.22. MSRP $185.00. 67% off.

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: Cognac Grainy
Price: $60.22MSRP: $185.0067% OFF
Rating

Steve Madden - Jules. Color Black/ Black. $120.00.

Black Steve Madden Jules

Black Steve Madden Jules

Brand Name: Steve Madden
Product Name: Jules
Gender: Men's
Color: Black/ Black
Price: $120.00
Rating

Dockers - Vaughn. Color Dark Brown. On sale for $59.99. MSRP $85.00. 29% off.

Brown Dockers Vaughn

Brown Dockers Vaughn

+2

Brand Name: Dockers
Product Name: Vaughn
Gender: Men's
Color: Dark Brown
Price: $59.99MSRP: $85.0029% OFF
Rating

Steve Madden - Crescent. Color Black Velvet. $100.00.

Black Steve Madden Crescent

Black Steve Madden Crescent

Brand Name: Steve Madden
Product Name: Crescent
Gender: Men's
Color: Black Velvet
Price: $100.00
Rating

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

Low Stock

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

. Tommy Hilfiger - Ladden. Color Tan. $99.00.

Tan Tommy Hilfiger Ladden

Tan Tommy Hilfiger Ladden

Brand Name: Tommy Hilfiger
Product Name: Ladden
Gender: Men's
Color: Tan
Price: $99.00
Rating

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.)