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

Size 9.5 Penny Keeper Casual Shoes

62 items found

Sort By

Your Selections

Search Results

. Marc Joseph New York - River Road. Color Brown Grainy. $185.00.

Brown Marc Joseph New York River Road

Brown Marc Joseph New York River Road

Brand Name: Marc Joseph New York
Product Name: River Road
Color: Brown Grainy
Price: $185.00
Rating

Rockport - Classic Loafer Lite Penny. Color Black II. On sale for $79.95. MSRP $115.00.. 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
Color: Black II
Price: $79.95MSRP: $115.00
Rating: 4Rated 4 stars out of 5(396)

Cole Haan - Hawthorne Penny Loafer. Color Black. On sale for $99.97. MSRP $110.00.. 3.0 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
Color: Black
Price: $99.97MSRP: $110.00
Rating: 3Rated 3 stars out of 5(2)

Florsheim - Throttle Penny. Color Brown Crazy Horse II. On sale for $79.95. MSRP $110.00.. 4.3 out of 5 stars

Brown Florsheim Throttle Penny

Brown Florsheim Throttle Penny

+3

Brand Name: Florsheim
Product Name: Throttle Penny
Color: Brown Crazy Horse II
Price: $79.95MSRP: $110.00
Rating: 4Rated 4 stars out of 5(12)

Cole Haan - Pinch Weekender Penny Textured. Color British Tan/Ivory. $100.00. 4.0 out of 5 stars

Brown Cole Haan Pinch Weekender Penny Textured

Brown Cole Haan Pinch Weekender Penny Textured

+5

Brand Name: Cole Haan
Product Name: Pinch Weekender Penny Textured
Color: British Tan/Ivory
Price: $100.00
Rating: 4Rated 4 stars out of 5(2)

Polo Ralph Lauren - Anders Penny. Color Brown. $168.00. 4.0 out of 5 stars

Brown Polo Ralph Lauren Anders Penny

Brown Polo Ralph Lauren Anders Penny

+2

Brand Name: Polo Ralph Lauren
Product Name: Anders Penny
Color: Brown
Price: $168.00
Rating: 4Rated 4 stars out of 5(1)

Polo Ralph Lauren - Alston Penny. Color Teak. $168.00.

Brown Polo Ralph Lauren Alston Penny

Brown Polo Ralph Lauren Alston Penny

+4

Brand Name: Polo Ralph Lauren
Product Name: Alston Penny
Color: Teak
Price: $168.00
Rating

Johnston & Murphy - Hayes Penny Loafer. Color Burgundy. On sale for $99.99. MSRP $135.00.. 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
Color: Burgundy
Price: $99.99MSRP: $135.00
Rating: 4Rated 4 stars out of 5(59)

Johnston & Murphy Collection - Baldwin Penny. Color Brandy. $195.00. 4.7 out of 5 stars

Brown Johnston & Murphy Collection Baldwin Penny

Brown Johnston & Murphy Collection Baldwin Penny

+4

Brand Name: Johnston & Murphy Collection
Product Name: Baldwin Penny
Color: Brandy
Price: $195.00
Rating: 5Rated 5 stars out of 5(26)

Nunn Bush - Noah Beef Roll Penny Loafer. Color Brown. On sale for $79.95. MSRP $100.00.. 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
Color: Brown
Price: $79.95MSRP: $100.00
Rating: 4Rated 4 stars out of 5(62)

Massimo Matteo - Florencia Penny Driver. Color Black. On sale for $53.10. MSRP $59.00.. 4.2 out of 5 stars

Black Massimo Matteo Florencia Penny Driver

Black Massimo Matteo Florencia Penny Driver

+3

Brand Name: Massimo Matteo
Product Name: Florencia Penny Driver
Color: Black
Price: $53.10MSRP: $59.00
Rating: 4Rated 4 stars out of 5(51)

Sperry - Cabo II Penny. Color Brown. On sale for $47.98. MSRP $109.95.. 3.8 out of 5 stars

Brown Sperry Cabo II Penny

Brown Sperry Cabo II Penny

+3

Brand Name: Sperry
Product Name: Cabo II Penny
Color: Brown
Price: $47.98MSRP: $109.95
Rating: 4Rated 4 stars out of 5(20)

COACH - Declan Loafer. Color Black. On sale for $192.50. MSRP $250.00.. 4.5 out of 5 stars

Black COACH Declan Loafer

Black COACH Declan Loafer

+1

Brand Name: COACH
Product Name: Declan Loafer
Color: Black
Price: $192.50MSRP: $250.00
Rating: 5Rated 5 stars out of 5(2)

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

+3

Brand Name: Cole Haan
Product Name: American Classics Penny Loafer
Color: Black/Black
Price: $158.00
Rating: 4Rated 4 stars out of 5(341)

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

Brown Steve Madden Ramsee

Brown Steve Madden Ramsee

+4

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

Florsheim - Zaffiro Moc Toe Penny Loafer. Color Black. $129.95. 5.0 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
Color: Black
Price: $129.95
Rating: 5Rated 5 stars out of 5(8)

Steve Madden - Vallme. Color Black. $69.99.

Black Steve Madden Vallme

Black Steve Madden Vallme

Brand Name: Steve Madden
Product Name: Vallme
Color: Black
Price: $69.99
Rating

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

Brown Sperry Authentic Original Penny

Brown Sperry Authentic Original Penny

+3

Brand Name: Sperry
Product Name: Authentic Original Penny
Color: Brown
Price: $109.90
Rating: 4Rated 4 stars out of 5(30)

ECCO - S Lite Moc Penny Loafer. Color Cognac. $169.95. 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
Color: Cognac
Price: $169.95
Rating: 4Rated 4 stars out of 5(4)

Born - Andes. Color Dark Brown. $110.00. 4.0 out of 5 stars

Brown Born Andes

Brown Born Andes

+2

Brand Name: Born
Product Name: Andes
Color: Dark Brown
Price: $110.00
Rating: 4Rated 4 stars out of 5(40)

Cole Haan - Pinch Weekender Penny. Color Sesame/Angora. On sale for $83.59. MSRP $120.00.. 4.3 out of 5 stars

Beige Cole Haan Pinch Weekender Penny

Beige Cole Haan Pinch Weekender Penny

+9

Brand Name: Cole Haan
Product Name: Pinch Weekender Penny
Color: Sesame/Angora
Price: $83.59MSRP: $120.00
Rating: 4Rated 4 stars out of 5(3)

Clarks - Markman Way. Color Dark Tan Leather. On sale for $89.99. MSRP $100.00.. 2.5 out of 5 stars

Brown Clarks Markman Way

Brown Clarks Markman Way

Brand Name: Clarks
Product Name: Markman Way
Color: Dark Tan Leather
Price: $89.99MSRP: $100.00
Rating: 2Rated 2 stars out of 5(17)

Sperry - Topsfield Penny Loafer. Color Black 1. $129.95. 4.3 out of 5 stars

Black Sperry Topsfield Penny Loafer

Black Sperry Topsfield Penny Loafer

+2

Brand Name: Sperry
Product Name: Topsfield Penny Loafer
Color: Black 1
Price: $129.95
Rating: 4Rated 4 stars out of 5(27)

Samuel Hubbard - Free Spirit for Him. Color Brown Leather. Low Stock. $195.00. 3.0 out of 5 stars

7 left in stock

Brown Samuel Hubbard Free Spirit for Him

Brown Samuel Hubbard Free Spirit for Him

+3

Brand Name: Samuel Hubbard
Product Name: Free Spirit for Him
Color: Brown Leather
Price: $195.00
Rating: 3Rated 3 stars out of 5(2)

Rockport - TruFlex DresSports Penny. Color New Dress Blues. On sale for $100.42. MSRP $119.95.. 5.0 out of 5 stars

Blue Rockport TruFlex DresSports Penny

Blue Rockport TruFlex DresSports Penny

+4

Brand Name: Rockport
Product Name: TruFlex DresSports Penny
Color: New Dress Blues
Price: $100.42MSRP: $119.95
Rating: 5Rated 5 stars out of 5(2)

Marc Joseph New York - Valley Road 2.0. Color Cognac Grainy. On sale for $79.95. MSRP $195.00.. 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
Color: Cognac Grainy
Price: $79.95MSRP: $195.00
Rating: 4Rated 4 stars out of 5(9)

Cole Haan - Pinch Prep Penny Loafer. Color Irish Coffee/Truffle Nubuck/Dark Sequoia. Low Stock. On sale for $99.97. MSRP $130.00.. 3.5 out of 5 stars

8 left in stock

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
Color: Irish Coffee/Truffle Nubuck/Dark Sequoia
Price: $99.97MSRP: $130.00
Rating

Dockers - Colleague. Color Tan. On sale for $49.95. MSRP $70.00.. 5.0 out of 5 stars

Tan Dockers Colleague

Tan Dockers Colleague

+2

Brand Name: Dockers
Product Name: Colleague
Color: Tan
Price: $49.95MSRP: $70.00
Rating: 5Rated 5 stars out of 5(1)

Steve Madden - Crescent. Color Black Velvet. $99.99.

Black Steve Madden Crescent

Black Steve Madden Crescent

Brand Name: Steve Madden
Product Name: Crescent
Color: Black Velvet
Price: $99.99
Rating

Born - Simon III. Color Black Full Grain. $120.00. 4.5 out of 5 stars

Black Born Simon III

Black Born Simon III

+2

Brand Name: Born
Product Name: Simon III
Color: Black Full Grain
Price: $120.00
Rating: 5Rated 5 stars out of 5(2)

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

Black Marc Joseph New York Union Street 2

Black Marc Joseph New York Union Street 2

+3

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

Frye - Tyler Penny. Color Almond. $257.95.

Brown Frye Tyler Penny

Brown Frye Tyler Penny

+4

Brand Name: Frye
Product Name: Tyler Penny
Color: Almond
Price: $257.95
Rating

Bruno Magli - Tonio. Color Dark Brown Cervo. On sale for $296.25. MSRP $395.00.. 5.0 out of 5 stars

Brown Bruno Magli Tonio

Brown Bruno Magli Tonio

+2 colors/patterns

Brand Name: Bruno Magli
Product Name: Tonio
Color: Dark Brown Cervo
Price: $296.25MSRP: $395.00
Rating: 5Rated 5 stars out of 5(1)

Marc Joseph New York - Washington. Color Black Napa. On sale for $72.15. MSRP $195.00.. 4.4 out of 5 stars

Black Marc Joseph New York Washington

Black Marc Joseph New York Washington

+3

Brand Name: Marc Joseph New York
Product Name: Washington
Color: Black Napa
Price: $72.15MSRP: $195.00
Rating: 4Rated 4 stars out of 5(5)

Dockers - Colleague. Color Cordovan. On sale for $49.99. MSRP $70.00.. 2.0 out of 5 stars

Burgundy Dockers Colleague

Burgundy Dockers Colleague

Brand Name: Dockers
Product Name: Colleague
Color: Cordovan
Price: $49.99MSRP: $70.00
Rating: 2Rated 2 stars out of 5(1)

Marc Joseph New York - East Village Mens. Color Black Napa. On sale for $115.50. MSRP $175.00..

Black Marc Joseph New York East Village Mens

Black Marc Joseph New York East Village Mens

+1

Brand Name: Marc Joseph New York
Product Name: East Village Mens
Color: Black Napa
Price: $115.50MSRP: $175.00
Rating

Tommy Hilfiger - Tabaro. Color Cognac. $69.95.

Tan Tommy Hilfiger Tabaro

Tan Tommy Hilfiger Tabaro

Brand Name: Tommy Hilfiger
Product Name: Tabaro
Color: Cognac
Price: $69.95
Rating

Johnston & Murphy Collection - Dayton Penny Loafer. Color Brown. Low Stock. $245.00.

10 left in stock

Brown Johnston & Murphy Collection Dayton Penny Loafer

Brown Johnston & Murphy Collection Dayton Penny Loafer

Brand Name: Johnston & Murphy Collection
Product Name: Dayton Penny Loafer
Color: Brown
Price: $245.00
Rating

Cole Haan - Wyatt Bit Driver. Color Stormy Weather Nubuck Perf/Gum. $125.00. 4.3 out of 5 stars

Gray Cole Haan Wyatt Bit Driver

Gray Cole Haan Wyatt Bit Driver

+5

Brand Name: Cole Haan
Product Name: Wyatt Bit Driver
Color: Stormy Weather Nubuck Perf/Gum
Price: $125.00
Rating: 4Rated 4 stars out of 5(276)

Johnston & Murphy Collection - Baldwin Driver Penny. Color Cognac. $185.00. 3.7 out of 5 stars

Tan Johnston & Murphy Collection Baldwin Driver Penny

Tan Johnston & Murphy Collection Baldwin Driver Penny

+3

Brand Name: Johnston & Murphy Collection
Product Name: Baldwin Driver Penny
Color: Cognac
Price: $185.00
Rating: 4Rated 4 stars out of 5(3)

Allen Edmonds - Supersport Penny. Color Walnut. $300.00. 3.6 out of 5 stars

Brown Allen Edmonds Supersport Penny

Brown Allen Edmonds Supersport Penny

+4

Brand Name: Allen Edmonds
Product Name: Supersport Penny
Color: Walnut
Price: $300.00
Rating: 4Rated 4 stars out of 5(27)

johnnie-O - Moxy Leather Penny. Color Bourbon. Low Stock. On sale for $63.36. MSRP $198.00..

9 left in stock

Brown johnnie-O Moxy Leather Penny

Brown johnnie-O Moxy Leather Penny

Brand Name: johnnie-O
Product Name: Moxy Leather Penny
Color: Bourbon
Price: $63.36MSRP: $198.00
Rating

Marc Joseph New York - Milford Ave. Color Black Napa. Low Stock. On sale for $76.95. MSRP $165.00.. 5.0 out of 5 stars

5 left in stock

Black Marc Joseph New York Milford Ave

Black Marc Joseph New York Milford Ave

Brand Name: Marc Joseph New York
Product Name: Milford Ave
Color: Black Napa
Price: $76.95MSRP: $165.00
Rating: 5Rated 5 stars out of 5(2)

SAS - Woodlawn. Color Mahogany. On sale for $84.58. MSRP $234.95.. 3.0 out of 5 stars

Mahogany SAS Woodlawn

Mahogany SAS Woodlawn

Brand Name: SAS
Product Name: Woodlawn
Color: Mahogany
Price: $84.58MSRP: $234.95
Rating: 3Rated 3 stars out of 5(6)

Allen Edmonds - Randolph. Color Black Calf. $425.00. 3.2 out of 5 stars

Black Allen Edmonds Randolph

Black Allen Edmonds Randolph

Brand Name: Allen Edmonds
Product Name: Randolph
Color: Black Calf
Price: $425.00
Rating: 3Rated 3 stars out of 5(9)

Martin Dingman - All American Penny. Color Chestnut. Low Stock. $295.00. 1.0 out of 5 stars

6 left in stock

Brown Martin Dingman All American Penny

Brown Martin Dingman All American Penny

Brand Name: Martin Dingman
Product Name: All American Penny
Color: Chestnut
Price: $295.00
Rating: 1Rated 1 star out of 5(1)

Rockport - Modern Prep Penny. Color Burgundy. On sale for $82.00. MSRP $119.95.. 3.9 out of 5 stars

Burgundy Rockport Modern Prep Penny

Burgundy Rockport Modern Prep Penny

Brand Name: Rockport
Product Name: Modern Prep Penny
Color: Burgundy
Price: $82.00MSRP: $119.95
Rating: 4Rated 4 stars out of 5(191)

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

Brown Dockers Vaughn

Brown Dockers Vaughn

+2

Brand Name: Dockers
Product Name: Vaughn
Color: Dark Brown
Price: $59.99MSRP: $85.00
Rating

Magnanni - Lawford. Color Black. On sale for $422.75. MSRP $445.00..

Black Magnanni Lawford

Black Magnanni Lawford

+2

Brand Name: Magnanni
Product Name: Lawford
Color: Black
Price: $422.75MSRP: $445.00
Rating

Bruno Magli - Xane. Color Taupe Suede. Low Stock. On sale for $168.75. MSRP $225.00.. 4.3 out of 5 stars

4 left in stock

Taupe Bruno Magli Xane

Taupe Bruno Magli Xane

+4

Brand Name: Bruno Magli
Product Name: Xane
Color: Taupe Suede
Price: $168.75MSRP: $225.00
Rating: 4Rated 4 stars out of 5(3)

Anthony Veer - Gerry Penny Loafer. Color Black. Low Stock. $199.95. 2.0 out of 5 stars

8 left in stock

Black Anthony Veer Gerry Penny Loafer

Black Anthony Veer Gerry Penny Loafer

+2

Brand Name: Anthony Veer
Product Name: Gerry Penny Loafer
Color: Black
Price: $199.95
Rating: 2Rated 2 stars out of 5(1)

To Boot New York - Idris. Color Light Blue Suede. Low Stock. On sale for $152.75. MSRP $325.00.. 5.0 out of 5 stars

4 left in stock

Blue To Boot New York Idris

Blue To Boot New York Idris

+2

Brand Name: To Boot New York
Product Name: Idris
Color: Light Blue Suede
Price: $152.75MSRP: $325.00
Rating: 5Rated 5 stars out of 5(1)

Johnston & Murphy Collection - Jameson Penny. Color Brown. Low Stock. On sale for $213.75. MSRP $285.00.. 3.0 out of 5 stars

5 left in stock

Brown Johnston & Murphy Collection Jameson Penny

Brown Johnston & Murphy Collection Jameson Penny

Brand Name: Johnston & Murphy Collection
Product Name: Jameson Penny
Color: Brown
Price: $213.75MSRP: $285.00
Rating: 3Rated 3 stars out of 5(3)

Anthony Veer - Sherman Penny Loafer. Color Chocolate Brown. On sale for $127.42. MSRP $149.90.. 5.0 out of 5 stars

Brown Anthony Veer Sherman Penny Loafer

Brown Anthony Veer Sherman Penny Loafer

Brand Name: Anthony Veer
Product Name: Sherman Penny Loafer
Color: Chocolate Brown
Price: $127.42MSRP: $149.90
Rating: 5Rated 5 stars out of 5(3)

Johnston & Murphy Collection - Dayton Woven Penny. Color Brown Italian Calfskin. $245.00. 4.1 out of 5 stars

Brown Johnston & Murphy Collection Dayton Woven Penny

Brown Johnston & Murphy Collection Dayton Woven Penny

Brand Name: Johnston & Murphy Collection
Product Name: Dayton Woven Penny
Color: Brown Italian Calfskin
Price: $245.00
Rating: 4Rated 4 stars out of 5(10)

La Canadienne - Lorne. Color Biscotti Suede. $425.00.

Gold La Canadienne Lorne

Gold La Canadienne Lorne

Brand Name: La Canadienne
Product Name: Lorne
Color: Biscotti Suede
Price: $425.00
Rating

Vince - Eston. Color Cocoa Brown. Low Stock. On sale for $179.97. MSRP $375.00..

8 left in stock

Brown Vince Eston

Brown Vince Eston

+2

Brand Name: Vince
Product Name: Eston
Color: Cocoa Brown
Price: $179.97MSRP: $375.00
Rating

Tommy Hilfiger - Dime. Color Cognac. $69.95.

Tan Tommy Hilfiger Dime

Tan Tommy Hilfiger Dime

Brand Name: Tommy Hilfiger
Product Name: Dime
Color: Cognac
Price: $69.95
Rating

Steve Madden - Ewald. Color Navy Fabric. $95.00.

Blue Steve Madden Ewald

Blue Steve Madden Ewald

Brand Name: Steve Madden
Product Name: Ewald
Color: Navy Fabric
Price: $95.00
Rating

Allen Edmonds - Randolph Sneaker. Color Chili. Low Stock. $300.00. 4.2 out of 5 stars

10 left in stock

Brown Allen Edmonds Randolph Sneaker

Brown Allen Edmonds Randolph Sneaker

Brand Name: Allen Edmonds
Product Name: Randolph Sneaker
Color: Chili
Price: $300.00
Rating: 4Rated 4 stars out of 5(50)

Bruno Magli - Manfredo. Color Navy. Low Stock. On sale for $296.25. MSRP $395.00.. 4.7 out of 5 stars

6 left in stock

Navy Bruno Magli Manfredo

Navy Bruno Magli Manfredo

+1

Brand Name: Bruno Magli
Product Name: Manfredo
Color: Navy
Price: $296.25MSRP: $395.00
Rating: 5Rated 5 stars out of 5(3)

Mephisto - Alexis. Color Dark Brown. Low Stock. $348.95. 3.7 out of 5 stars

10 left in stock

Brown Mephisto Alexis

Brown Mephisto Alexis

+2

Brand Name: Mephisto
Product Name: Alexis
Color: Dark Brown
Price: $348.95
Rating: 4Rated 4 stars out of 5(3)

Get on the List

Subscribe to Zappos emails for exclusive product launches, early notifications for sales, and a few extra-special surprises.