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

Size 8.5 Penny Keeper Casual Shoes

49 items found

Sort By

Your Selections

Search Results

. Marc Joseph New York - River Road. Color Black Grainy. On sale for $69.95. MSRP $185.00..

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: $185.00
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
Gender: Men's
Color: Black II
Price: $79.95MSRP: $115.00
Rating: 4Rated 4 stars out of 5(396)

Cole Haan - Grand Laser Penny Driver. Color British Tan/Java. On sale for $93.16. MSRP $155.00.. 3.9 out of 5 stars

Beige Cole Haan Grand Laser Penny Driver

Beige Cole Haan Grand Laser Penny Driver

+2

Brand Name: Cole Haan
Product Name: Grand Laser Penny Driver
Gender: Men's
Color: British Tan/Java
Price: $93.16MSRP: $155.00
Rating: 4Rated 4 stars out of 5(68)

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
Gender: Men's
Color: Brown Crazy Horse II
Price: $79.95MSRP: $110.00
Rating: 4Rated 4 stars out of 5(13)

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
Gender: Men's
Color: Black/Black
Price: $158.00
Rating: 4Rated 4 stars out of 5(345)

Nunn Bush - Noah Beef Roll Penny Loafer. Color Black. On sale for $69.95. MSRP $100.00.. 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: $69.95MSRP: $100.00
Rating: 4Rated 4 stars out of 5(62)

Johnston & Murphy - Hayes Penny Loafer. Color Black. On sale for $99.99. MSRP $135.00.. 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: $99.99MSRP: $135.00
Rating: 4Rated 4 stars out of 5(60)

Cole Haan - Hawthorne Penny Loafer. Color Habana. $110.00. 3.0 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: $110.00
Rating: 3Rated 3 stars out of 5(2)

Cole Haan - Pinch Weekender Penny. Color Sesame/Angora. On sale for $89.95. MSRP $120.00.. 4.3 out of 5 stars

Beige Cole Haan Pinch Weekender Penny

Beige Cole Haan Pinch Weekender Penny

Brand Name: Cole Haan
Product Name: Pinch Weekender Penny
Gender: Men's
Color: Sesame/Angora
Price: $89.95MSRP: $120.00
Rating: 4Rated 4 stars out of 5(3)

Polo Ralph Lauren - Anders Penny. Color Brown. On sale for $117.60. MSRP $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
Gender: Men's
Color: Brown
Price: $117.60MSRP: $168.00
Rating: 4Rated 4 stars out of 5(1)

Polo Ralph Lauren - Alston Penny. Color Tan. $178.00.

Tan Polo Ralph Lauren Alston Penny

Tan Polo Ralph Lauren Alston Penny

+4

Brand Name: Polo Ralph Lauren
Product Name: Alston Penny
Gender: Men's
Color: Tan
Price: $178.00
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
Gender: Men's
Color: Brown
Price: $109.90
Rating: 4Rated 4 stars out of 5(30)

Tommy Hilfiger - Amile. Color Taupe. On sale for $46.74. MSRP $59.95.. 4.5 out of 5 stars

Taupe Tommy Hilfiger Amile

Taupe Tommy Hilfiger Amile

+3

Brand Name: Tommy Hilfiger
Product Name: Amile
Gender: Men's
Color: Taupe
Price: $46.74MSRP: $59.95
Rating: 5Rated 5 stars out of 5(4)

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
Gender: Men's
Color: Dark Tan Leather
Price: $89.99MSRP: $100.00
Rating: 2Rated 2 stars out of 5(17)

Peter Millar - Crown Knit Driver. Color Navy. $175.00. 3.0 out of 5 stars

Navy Peter Millar Crown Knit Driver

Navy Peter Millar Crown Knit Driver

Brand Name: Peter Millar
Product Name: Crown Knit Driver
Gender: Men's
Color: Navy
Price: $175.00
Rating: 3Rated 3 stars out of 5(2)

ECCO - S Lite Moc Penny Loafer. Color Black. $169.95. 4.0 out of 5 stars

Black ECCO S Lite Moc Penny Loafer

Black ECCO S Lite Moc Penny Loafer

+2

Brand Name: ECCO
Product Name: S Lite Moc Penny Loafer
Gender: Men's
Color: Black
Price: $169.95
Rating: 4Rated 4 stars out of 5(4)

Sperry - Cabo II Penny. Color Sand. $109.90. 3.8 out of 5 stars

Beige Sperry Cabo II Penny

Beige Sperry Cabo II Penny

+3

Brand Name: Sperry
Product Name: Cabo II Penny
Gender: Men's
Color: Sand
Price: $109.90
Rating: 4Rated 4 stars out of 5(20)

Cole Haan - Pinch Weekender Penny Textured. Color Black Pebbled Leather/Ivory. $100.00. 4.0 out of 5 stars

Black Cole Haan Pinch Weekender Penny Textured

Black Cole Haan Pinch Weekender Penny Textured

+5

Brand Name: Cole Haan
Product Name: Pinch Weekender Penny Textured
Gender: Men's
Color: Black Pebbled Leather/Ivory
Price: $100.00
Rating: 4Rated 4 stars out of 5(2)

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

Black Steve Madden Crescent

Black Steve Madden Crescent

Brand Name: Steve Madden
Product Name: Crescent
Gender: Men's
Color: Black Velvet
Price: $99.99
Rating

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
Gender: Men's
Color: Cognac
Price: $185.00
Rating: 4Rated 4 stars out of 5(3)

Marc Joseph New York - East Village Mens. Color Whiskey Napa. Low Stock. On sale for $126.00. MSRP $175.00..

5 left in stock

Tan Marc Joseph New York East Village Mens

Tan Marc Joseph New York East Village Mens

+1

Brand Name: Marc Joseph New York
Product Name: East Village Mens
Gender: Men's
Color: Whiskey Napa
Price: $126.00MSRP: $175.00
Rating

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

Blue Steve Madden Ramsee

Blue Steve Madden Ramsee

+3

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

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

Black Johnston & Murphy Collection Baldwin Penny

Black Johnston & Murphy Collection Baldwin Penny

+4

Brand Name: Johnston & Murphy Collection
Product Name: Baldwin Penny
Gender: Men's
Color: Black
Price: $195.00
Rating: 5Rated 5 stars out of 5(26)

Rockport - TruFlex DresSports Penny. Color New Dress Blues. On sale for $73.17. MSRP $119.95.. 5.0 out of 5 stars

Blue Rockport TruFlex DresSports Penny

Blue Rockport TruFlex DresSports Penny

+3

Brand Name: Rockport
Product Name: TruFlex DresSports Penny
Gender: Men's
Color: New Dress Blues
Price: $73.17MSRP: $119.95
Rating: 5Rated 5 stars out of 5(2)

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

Brown Born Andes

Brown Born Andes

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

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

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

Tan Born Simon III

Tan Born Simon III

+2

Brand Name: Born
Product Name: Simon III
Gender: Men's
Color: Tan Full Grain
Price: $120.00
Rating: 5Rated 5 stars out of 5(2)

Dockers - Colleague. Color Tan. On sale for $49.95. MSRP $70.00.. 3.5 out of 5 stars

Tan Dockers Colleague

Tan Dockers Colleague

+2

Brand Name: Dockers
Product Name: Colleague
Gender: Men's
Color: Tan
Price: $49.95MSRP: $70.00
Rating: 4Rated 4 stars out of 5(2)

Nunn Bush - Centro Flex Moccasin Toe Penny Loafer Slip-On. Color Black. On sale for $79.95. MSRP $100.00.. 4.9 out of 5 stars

Black Nunn Bush Centro Flex Moccasin Toe Penny Loafer Slip-On

Black Nunn Bush Centro Flex Moccasin Toe Penny Loafer Slip-On

Brand Name: Nunn Bush
Product Name: Centro Flex Moccasin Toe Penny Loafer Slip-On
Gender: Men's
Color: Black
Price: $79.95MSRP: $100.00
Rating: 5Rated 5 stars out of 5(7)

To Boot New York - O'Conner. Color Windsor Bruciato. Low Stock. On sale for $159.60. MSRP $399.00.. 1.0 out of 5 stars

2 left in stock

Burgundy To Boot New York O'Conner

Burgundy To Boot New York O'Conner

Brand Name: To Boot New York
Product Name: O'Conner
Gender: Men's
Color: Windsor Bruciato
Price: $159.60MSRP: $399.00
Rating: 1Rated 1 star out of 5(1)

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

Black Marc Joseph New York Valley Road 2.0

Black 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: Black Grainy
Price: $79.95MSRP: $195.00
Rating: 4Rated 4 stars out of 5(9)

Samuel Hubbard - Free Spirit for Him. Color Black Tumbled Leather. $195.00. 3.0 out of 5 stars

Black Samuel Hubbard Free Spirit for Him

Black Samuel Hubbard Free Spirit for Him

+3

Brand Name: Samuel Hubbard
Product Name: Free Spirit for Him
Gender: Men's
Color: Black Tumbled Leather
Price: $195.00
Rating: 3Rated 3 stars out of 5(2)

Tommy Hilfiger - Dime. Color Cognac. On sale for $67.91. MSRP $69.95..

Tan Tommy Hilfiger Dime

Tan Tommy Hilfiger Dime

Brand Name: Tommy Hilfiger
Product Name: Dime
Gender: Men's
Color: Cognac
Price: $67.91MSRP: $69.95
Rating

Marc Joseph New York - Union Street 2. Color Tan Burnished Nappa. $155.00. 4.8 out of 5 stars

Tan Marc Joseph New York Union Street 2

Tan Marc Joseph New York Union Street 2

+2

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

Tommy Hilfiger - Tabaro. Color Cognac. $69.30.

Tan Tommy Hilfiger Tabaro

Tan Tommy Hilfiger Tabaro

Brand Name: Tommy Hilfiger
Product Name: Tabaro
Gender: Men's
Color: Cognac
Price: $69.30
Rating

Marc Joseph New York - Washington. Color Whiskey Napa. Low Stock. On sale for $79.95. MSRP $195.00.. 4.4 out of 5 stars

2 left in stock

Tan Marc Joseph New York Washington

Tan Marc Joseph New York Washington

+3

Brand Name: Marc Joseph New York
Product Name: Washington
Gender: Men's
Color: Whiskey Napa
Price: $79.95MSRP: $195.00
Rating: 4Rated 4 stars out of 5(5)

Marc Joseph New York - Milford Ave. Color Havana Grainy. On sale for $110.55. MSRP $165.00.. 5.0 out of 5 stars

Mahogany Marc Joseph New York Milford Ave

Mahogany Marc Joseph New York Milford Ave

Brand Name: Marc Joseph New York
Product Name: Milford Ave
Gender: Men's
Color: Havana Grainy
Price: $110.55MSRP: $165.00
Rating: 5Rated 5 stars out of 5(2)

Bruno Magli - Eduardo. Color Cognac Suede. Low Stock. On sale for $100.00. MSRP $250.00.. 5.0 out of 5 stars

1 left in stock

Brown Bruno Magli Eduardo

Brown Bruno Magli Eduardo

Brand Name: Bruno Magli
Product Name: Eduardo
Gender: Men's
Color: Cognac Suede
Price: $100.00MSRP: $250.00
Rating: 5Rated 5 stars out of 5(1)

PIKOLINOS - Avila M1T-3205. Color Black. $189.95. 5.0 out of 5 stars

Black PIKOLINOS Avila M1T-3205

Black PIKOLINOS Avila M1T-3205

+2

Brand Name: PIKOLINOS
Product Name: Avila M1T-3205
Gender: Men's
Color: Black
Price: $189.95
Rating: 5Rated 5 stars out of 5(1)

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
Gender: Men's
Color: Cordovan
Price: $49.99MSRP: $70.00
Rating: 2Rated 2 stars out of 5(1)

Anthony Veer - Gerry Penny Loafer. Color Black. Low Stock. On sale for $139.96. MSRP $199.95.. 2.0 out of 5 stars

6 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
Gender: Men's
Color: Black
Price: $139.96MSRP: $199.95
Rating: 2Rated 2 stars out of 5(1)

Anthony Veer - Sherman Penny Loafer. Color Chocolate Brown. On sale for $121.66. 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
Gender: Men's
Color: Chocolate Brown
Price: $121.66MSRP: $149.90
Rating: 5Rated 5 stars out of 5(3)

Marc Joseph New York - Lexington. Color Brown Nappa Leather. Low Stock. On sale for $140.40. MSRP $195.00.. 4.2 out of 5 stars

5 left in stock

Brown Marc Joseph New York Lexington

Brown Marc Joseph New York Lexington

+3

Brand Name: Marc Joseph New York
Product Name: Lexington
Gender: Men's
Color: Brown Nappa Leather
Price: $140.40MSRP: $195.00
Rating: 4Rated 4 stars out of 5(5)

Johnston & Murphy - Cort Penny. Color Black Full Grain Leather. Low Stock. $145.00. 4.5 out of 5 stars

3 left in stock

Black Johnston & Murphy Cort Penny

Black Johnston & Murphy Cort Penny

+2

Brand Name: Johnston & Murphy
Product Name: Cort Penny
Gender: Men's
Color: Black Full Grain Leather
Price: $145.00
Rating: 5Rated 5 stars out of 5(76)

Vince Camuto - Lamcy. Color Cognac/Brown. Low Stock. On sale for $105.79. MSRP $149.00.. 4.0 out of 5 stars

6 left in stock

Brown Vince Camuto Lamcy

Brown Vince Camuto Lamcy

Brand Name: Vince Camuto
Product Name: Lamcy
Gender: Men's
Color: Cognac/Brown
Price: $105.79MSRP: $149.00
Rating: 4Rated 4 stars out of 5(1)

Born - Taylor. Color Brown Full Grain Leather. Low Stock. On sale for $109.20. MSRP $120.00.. 4.0 out of 5 stars

1 left in stock

Brown Born Taylor

Brown Born Taylor

+2

Brand Name: Born
Product Name: Taylor
Gender: Men's
Color: Brown Full Grain Leather
Price: $109.20MSRP: $120.00
Rating: 4Rated 4 stars out of 5(5)

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
Gender: Men's
Color: Dark Brown
Price: $59.99MSRP: $85.00
Rating

Thomas & Vine - Watkins Embossed Penny Loafer. Color Cognac. Low Stock. On sale for $104.99. MSRP $149.99.. 2.5 out of 5 stars

5 left in stock

Tan Thomas & Vine Watkins Embossed Penny Loafer

Tan Thomas & Vine Watkins Embossed Penny Loafer

Brand Name: Thomas & Vine
Product Name: Watkins Embossed Penny Loafer
Gender: Men's
Color: Cognac
Price: $104.99MSRP: $149.99
Rating: 3Rated 3 stars out of 5(6)

Carlos by Carlos Santana - Ritchie Driver Loafer. Color Olive Calf Nubuck. Low Stock. On sale for $76.29. MSRP $88.95.. 3.7 out of 5 stars

8 left in stock

Brown Carlos by Carlos Santana Ritchie Driver Loafer

Brown Carlos by Carlos Santana Ritchie Driver Loafer

+2

Brand Name: Carlos by Carlos Santana
Product Name: Ritchie Driver Loafer
Gender: Men's
Color: Olive Calf Nubuck
Price: $76.29MSRP: $88.95
Rating: 4Rated 4 stars out of 5(7)

Get on the List

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