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

Size 9.5 Penny Keeper Shoes

52 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(407)

Florsheim - Berkley Flex Penny Loafer. Color Brown Crazy Horse. On sale for $108.00. MSRP $125.00. 14% 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: $108.00MSRP: $125.0014% OFF
Rating: 4Rated 4 stars out of 5(185)

Cole Haan - Nanctucket Penny Loafer. Color British Tan/Ivory. $90.00. 4.3 out of 5 stars

Brown Cole Haan Nanctucket Penny Loafer

Brown Cole Haan Nanctucket Penny Loafer

+4

Brand Name: Cole Haan
Product Name: Nanctucket Penny Loafer
Gender: Men's
Color: British Tan/Ivory
Price: $90.00
Rating: 4Rated 4 stars out of 5(3)

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

Brown Marc Joseph New York Nebraska

Brown Marc Joseph New York Nebraska

+7

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

. Cole Haan - Grand Laser Penny Driver. Color Light Sesame Suede/Gum. $140.00. 3.9 out of 5 stars

Gray Cole Haan Grand Laser Penny Driver

Gray Cole Haan Grand Laser Penny Driver

+5

Brand Name: Cole Haan
Product Name: Grand Laser Penny Driver
Gender: Men's
Color: Light Sesame Suede/Gum
Price: $140.00
Rating: 4Rated 4 stars out of 5(70)

Cole Haan - Pinch Prep Penny Loafer. Color Scotch. $111.46. 4.1 out of 5 stars

Brown Cole Haan Pinch Prep Penny Loafer

Brown Cole Haan Pinch Prep Penny Loafer

+9

Brand Name: Cole Haan
Product Name: Pinch Prep Penny Loafer
Gender: Men's
Color: Scotch
Price: $111.46
Rating: 4Rated 4 stars out of 5(8)

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

Brown Marc Joseph New York Valley Road 2.0

Brown Marc Joseph New York Valley Road 2.0

+4

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(9)

Dockers - Colleague. Color Cordovan. On sale for $50.24. 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: $50.24MSRP: $70.0028% OFF
Rating: 2Rated 2 stars out of 5(1)

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

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(15)

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(358)

Johnston & Murphy - Hayes Penny Loafer. Color Black. On sale for $95.00. MSRP $135.00. 30% off. 4.0 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: $95.00MSRP: $135.0030% OFF
Rating: 4Rated 4 stars out of 5(103)

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(111)

Marc Joseph New York - Monaco. Color Cognac Grainy. On sale for $60.97. 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: $60.97MSRP: $185.0067% OFF
Rating

Tommy Hilfiger - Amile. Color Black. On sale for $64.99. MSRP $85.00. 24% off. 4.6 out of 5 stars

Black Tommy Hilfiger Amile

Black Tommy Hilfiger Amile

+4

Brand Name: Tommy Hilfiger
Product Name: Amile
Gender: Men's
Color: Black
Price: $64.99MSRP: $85.0024% OFF
Rating: 5Rated 5 stars out of 5(5)

Cole Haan - Hawthorne Penny Loafer. Color Black. $110.00. 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: $110.00
Rating: 4Rated 4 stars out of 5(4)

Florsheim - Zaffiro Moc Toe Penny Loafer. Color Black. On sale for $119.99. MSRP $130.00. 8% off. 4.6 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: $119.99MSRP: $130.008% OFF
Rating: 5Rated 5 stars out of 5(13)

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)

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)

Nunn Bush - Drexel Moc Toe Penny Loafer with KORE Walking Comfort Technology. Color Cognac. On sale for $74.95. MSRP $100.00. 25% 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: $74.95MSRP: $100.0025% OFF
Rating: 4Rated 4 stars out of 5(166)

Cole Haan - Wyatt Penny Driver. Color Black/Black. $105.50. 4.3 out of 5 stars

Black Cole Haan Wyatt Penny Driver

Black Cole Haan Wyatt Penny Driver

+3

Brand Name: Cole Haan
Product Name: Wyatt Penny Driver
Gender: Men's
Color: Black/Black
Price: $105.50
Rating: 4Rated 4 stars out of 5(282)

Tommy Hilfiger - Simol. Color Cognac. On sale for $69.99. MSRP $99.00. 29% off. 3.0 out of 5 stars

Tan Tommy Hilfiger Simol

Tan Tommy Hilfiger Simol

+2

Brand Name: Tommy Hilfiger
Product Name: Simol
Gender: Men's
Color: Cognac
Price: $69.99MSRP: $99.0029% OFF
Rating: 3Rated 3 stars out of 5(2)

Tommy Hilfiger - Tabaro. Color Cognac. On sale for $89.10. MSRP $99.00. 10% off.

Tan Tommy Hilfiger Tabaro

Tan Tommy Hilfiger Tabaro

Brand Name: Tommy Hilfiger
Product Name: Tabaro
Gender: Men's
Color: Cognac
Price: $89.10MSRP: $99.0010% OFF
Rating

Nunn Bush - Lincoln Penny Loafer. Color Burgundy Polished. On sale for $69.95. MSRP $95.00. 26% 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: $95.0026% OFF
Rating: 4Rated 4 stars out of 5(310)

Dockers - Colleague. Color Cordovan. On sale for $49.00. MSRP $79.00. 38% off. 3.5 out of 5 stars

Burgundy Dockers Colleague

Burgundy Dockers Colleague

+3

Brand Name: Dockers
Product Name: Colleague
Gender: Men's
Color: Cordovan
Price: $49.00MSRP: $79.0038% OFF
Rating: 4Rated 4 stars out of 5(2)

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(47)

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

+6

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)

COACH - Declan Loafer. Color Midnight Navy. On sale for $150.96. MSRP $250.00. 40% 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: $150.96MSRP: $250.0040% OFF
Rating: 5Rated 5 stars out of 5(4)

Frye - Tyler Flex Penny. Color Mushroom. $197.95. 3.5 out of 5 stars

Gray Frye Tyler Flex Penny

Gray Frye Tyler Flex Penny

+4

Brand Name: Frye
Product Name: Tyler Flex Penny
Gender: Men's
Color: Mushroom
Price: $197.95
Rating: 4Rated 4 stars out of 5(2)

Marc Joseph New York - River Road. Color Black Grainy. On sale for $69.95. MSRP $185.00. 62% 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: $69.95MSRP: $185.0062% OFF
Rating: 5Rated 5 stars out of 5(1)

Clarks - Markman Way. Color Dark Tan Leather. On sale for $80.00. MSRP $100.00. 20% off. 2.5 out of 5 stars

Brown Clarks Markman Way

Brown Clarks Markman Way

Brand Name: Clarks
Product Name: Markman Way
Gender: Men's
Color: Dark Tan Leather
Price: $80.00MSRP: $100.0020% OFF
Rating: 3Rated 3 stars out of 5(20)

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)

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

Taupe Polo Ralph Lauren Anders Penny

Taupe Polo Ralph Lauren Anders Penny

+3

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

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

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

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

Brown Steve Madden Ramsee

Brown Steve Madden Ramsee

+3

Brand Name: Steve Madden
Product Name: Ramsee
Gender: Men's
Color: Tobacco
Price: $120.00
Rating: 4Rated 4 stars out of 5(10)

Sperry - Authentic Original Penny. Color Navy. $109.90. 4.4 out of 5 stars

Navy Sperry Authentic Original Penny

Navy Sperry Authentic Original Penny

+3

Brand Name: Sperry
Product Name: Authentic Original Penny
Gender: Men's
Color: Navy
Price: $109.90
Rating: 4Rated 4 stars out of 5(31)

Rockport - Liam. Color Black Leather. $129.95. 4.0 out of 5 stars

Black Rockport Liam

Black Rockport Liam

+1

Brand Name: Rockport
Product Name: Liam
Gender: Men's
Color: Black Leather
Price: $129.95
Rating: 4Rated 4 stars out of 5(2)

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

Navy Dockers Vaughn

Navy Dockers Vaughn

+2

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

Stacy Adams - Spencer Penny Slip-On. Color Burgundy. On sale for $90.87. MSRP $120.00. 24% 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: $90.87MSRP: $120.0024% OFF
Rating: 5Rated 5 stars out of 5(3)

ALDO - Legolas. Color Navy. On sale for $107.52. MSRP $128.00. 16% off.

Navy ALDO Legolas

Navy ALDO Legolas

+2

Brand Name: ALDO
Product Name: Legolas
Gender: Men's
Color: Navy
Price: $107.52MSRP: $128.0016% OFF
Rating

Born - Simon III. Color Tan Full Grain. $120.00. 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: $120.00
Rating: 3Rated 3 stars out of 5(3)

Johnston & Murphy Collection - Baldwin Driver Penny. Color Black. On sale for $166.50. MSRP $185.00. 10% off. 4.0 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: $166.50MSRP: $185.0010% OFF
Rating: 4Rated 4 stars out of 5(28)

Marc Joseph New York - East Village Mens. Color Whiskey Napa. Low Stock. On sale for $110.25. MSRP $175.00. 37% off.

Low Stock

Tan Marc Joseph New York East Village Mens

Tan Marc Joseph New York East Village Mens

Brand Name: Marc Joseph New York
Product Name: East Village Mens
Gender: Men's
Color: Whiskey Napa
Price: $110.25MSRP: $175.0037% OFF
Rating

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

Olive Marc Joseph New York Union Street 2

Olive Marc Joseph New York Union Street 2

+4

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

Sperry - Cabo II Penny. Color Sand. $109.90. 3.9 out of 5 stars

Beige Sperry Cabo II Penny

Beige Sperry Cabo II Penny

Brand Name: Sperry
Product Name: Cabo II Penny
Gender: Men's
Color: Sand
Price: $109.90
Rating: 4Rated 4 stars out of 5(21)

SAS - Woodlawn. Color Licorice. On sale for $136.27. MSRP $234.95. 42% off. 3.0 out of 5 stars

Multi SAS Woodlawn

Multi SAS Woodlawn

Brand Name: SAS
Product Name: Woodlawn
Gender: Men's
Color: Licorice
Price: $136.27MSRP: $234.9542% OFF
Rating: 3Rated 3 stars out of 5(6)

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(100)

Marc Joseph New York - Lexington. Color Brown Suede. Low Stock. On sale for $154.05. MSRP $195.00. 21% off. 4.2 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(5)

Johnston & Murphy Collection - Damon Penny. Color Black Italian Calfskin. Low Stock. On sale for $171.60. MSRP $195.00. 12% off.

Low Stock

Black Johnston & Murphy Collection Damon Penny

Black Johnston & Murphy Collection Damon Penny

Brand Name: Johnston & Murphy Collection
Product Name: Damon Penny
Gender: Men's
Color: Black Italian Calfskin
Price: $171.60MSRP: $195.0012% OFF
Rating

johnnie-O - Moxy Leather Penny. Color Bourbon. Low Stock. On sale for $122.76. MSRP $198.00. 38% off.

Low Stock

Brown johnnie-O Moxy Leather Penny

Brown johnnie-O Moxy Leather Penny

Brand Name: johnnie-O
Product Name: Moxy Leather Penny
Gender: Men's
Color: Bourbon
Price: $122.76MSRP: $198.0038% OFF
Rating

Tommy Hilfiger - Dime. Color Cognac. On sale for $74.25. MSRP $99.00. 25% off.

Tan Tommy Hilfiger Dime

Tan Tommy Hilfiger Dime

Brand Name: Tommy Hilfiger
Product Name: Dime
Gender: Men's
Color: Cognac
Price: $74.25MSRP: $99.0025% OFF
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.)