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

Men's Penny Keeper Shoes

50 items found

Sort By

Your Selections

Search Results

Cole Haan - Grand Laser Penny Driver. Color British Tan/Java. On sale for $93.80. MSRP $155.00.. 3.9 out of 5 stars

Beige Cole Haan Grand Laser Penny Driver

Beige Cole Haan Grand Laser Penny Driver

+3

Brand Name: Cole Haan
Product Name: Grand Laser Penny Driver
Gender: Men's
Color: British Tan/Java
Price: $93.80MSRP: $155.00
Rating: 4Rated 4 stars out of 5(68)

Rockport - Classic Loafer Lite Penny. Color Dark Brown. On sale for $79.95. MSRP $115.00.. 3.9 out of 5 stars

Brown Rockport Classic Loafer Lite Penny

Brown Rockport Classic Loafer Lite Penny

+3

Brand Name: Rockport
Product Name: Classic Loafer Lite Penny
Gender: Men's
Color: Dark Brown
Price: $79.95MSRP: $115.00
Rating: 4Rated 4 stars out of 5(396)

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)

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
Gender: Men's
Color: Black
Price: $99.97MSRP: $110.00
Rating: 3Rated 3 stars out of 5(2)

Florsheim - Midtown Penny Slip-On. Color Black Smooth. On sale for $89.95. MSRP $125.00.. 4.4 out of 5 stars

Black Florsheim Midtown Penny Slip-On

Black Florsheim Midtown Penny Slip-On

+2

Brand Name: Florsheim
Product Name: Midtown Penny Slip-On
Gender: Men's
Color: Black Smooth
Price: $89.95MSRP: $125.00
Rating: 4Rated 4 stars out of 5(88)

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
Gender: Men's
Color: Burgundy
Price: $99.99MSRP: $135.00
Rating: 4Rated 4 stars out of 5(56)

Marc Joseph New York - Nebraska. Color Black Grainy. On sale for $79.95. MSRP $185.00.. 4.5 out of 5 stars

Black Marc Joseph New York Nebraska

Black Marc Joseph New York Nebraska

+10

Brand Name: Marc Joseph New York
Product Name: Nebraska
Gender: Men's
Color: Black Grainy
Price: $79.95MSRP: $185.00
Rating: 5Rated 5 stars out of 5(6)

Nunn Bush - Drexel Moc Toe Penny Loafer with KORE Walking Comfort Technology. Color Cognac. On sale for $74.95. MSRP $100.00.. 4.4 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: $100.00
Rating: 4Rated 4 stars out of 5(154)

Peter Millar - Crown Knit Driver. Color Chocolate. Low Stock. On sale for $98.00. MSRP $175.00.. 3.0 out of 5 stars

3 left in stock

Brown Peter Millar Crown Knit Driver

Brown Peter Millar Crown Knit Driver

Brand Name: Peter Millar
Product Name: Crown Knit Driver
Gender: Men's
Color: Chocolate
Price: $98.00MSRP: $175.00
Rating: 3Rated 3 stars out of 5(2)

Steve Madden - Vallme. Color Cognac. $69.99.

Tan Steve Madden Vallme

Tan Steve Madden Vallme

Brand Name: Steve Madden
Product Name: Vallme
Gender: Men's
Color: Cognac
Price: $69.99
Rating

Florsheim - Throttle Penny. Color Cognac. On sale for $69.95. MSRP $110.00.. 4.3 out of 5 stars

Tan Florsheim Throttle Penny

Tan Florsheim Throttle Penny

+3

Brand Name: Florsheim
Product Name: Throttle Penny
Gender: Men's
Color: Cognac
Price: $69.95MSRP: $110.00
Rating: 4Rated 4 stars out of 5(11)

Marc Joseph New York - Lexington. Color Black Nappa Leather. Low Stock. On sale for $80.73. MSRP $195.00.. 4.2 out of 5 stars

3 left in stock

Black Marc Joseph New York Lexington

Black Marc Joseph New York Lexington

+3

Brand Name: Marc Joseph New York
Product Name: Lexington
Gender: Men's
Color: Black Nappa Leather
Price: $80.73MSRP: $195.00
Rating: 4Rated 4 stars out of 5(5)

Sperry - Authentic Original Penny. Color Brown. On sale for $93.46. MSRP $109.95.. 4.5 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: $93.46MSRP: $109.95
Rating: 4Rated 4 stars out of 5(26)

Nunn Bush - Lincoln Penny Loafer. Color Burgundy Polished. On sale for $64.95. MSRP $90.00.. 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: $64.95MSRP: $90.00
Rating: 4Rated 4 stars out of 5(293)

Massimo Matteo - Florencia Penny Driver. Color Black. $59.00. 4.2 out of 5 stars

Black Massimo Matteo Florencia Penny Driver

Black Massimo Matteo Florencia Penny Driver

+2

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

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)

Johnston & Murphy - Lewis Penny. Color Tan Full Grain Leather. Low Stock. On sale for $99.99. MSRP $149.00.. 4.3 out of 5 stars

2 left in stock

Tan Johnston & Murphy Lewis Penny

Tan Johnston & Murphy Lewis Penny

Brand Name: Johnston & Murphy
Product Name: Lewis Penny
Gender: Men's
Color: Tan Full Grain Leather
Price: $99.99MSRP: $149.00
Rating: 4Rated 4 stars out of 5(23)

Cole Haan - American Classics Pinch Penny Loafer. Color Irish Coffee/Truffle Nubuck/Dark Sequoia. On sale for $99.97. MSRP $130.00..

Brown Cole Haan American Classics Pinch Penny Loafer

Brown Cole Haan American Classics Pinch Penny Loafer

Brand Name: Cole Haan
Product Name: American Classics Pinch Penny Loafer
Gender: Men's
Color: Irish Coffee/Truffle Nubuck/Dark Sequoia
Price: $99.97MSRP: $130.00
Rating

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

Black Dockers Colleague

Black Dockers Colleague

+2

Brand Name: Dockers
Product Name: Colleague
Gender: Men's
Color: Black
Price: $49.95MSRP: $70.00
Rating: 5Rated 5 stars out of 5(1)

Cole Haan - Pinch Weekender Penny. Color Sesame/Angora. On sale for $90.00. MSRP $120.00..

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: $90.00MSRP: $120.00
Rating

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)

Sperry - Cabo II Penny. Color Sand. On sale for $93.46. MSRP $109.95.. 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: $93.46MSRP: $109.95
Rating: 4Rated 4 stars out of 5(20)

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
Gender: Men's
Color: Cognac Grainy
Price: $79.95MSRP: $195.00
Rating: 4Rated 4 stars out of 5(9)

Cole Haan - Wyatt Bit Driver. Color Black. On sale for $80.00. MSRP $105.00.. 4.3 out of 5 stars

Black Cole Haan Wyatt Bit Driver

Black Cole Haan Wyatt Bit Driver

+5

Brand Name: Cole Haan
Product Name: Wyatt Bit Driver
Gender: Men's
Color: Black
Price: $80.00MSRP: $105.00
Rating: 4Rated 4 stars out of 5(276)

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)

Born - Andes. Color Orange/Brown Full Grain. Low Stock. On sale for $58.30. MSRP $110.00.. 4.0 out of 5 stars

9 left in stock

Orange Born Andes

Orange Born Andes

+2

Brand Name: Born
Product Name: Andes
Gender: Men's
Color: Orange/Brown Full Grain
Price: $58.30MSRP: $110.00
Rating: 4Rated 4 stars out of 5(40)

Thomas & Vine - Bishop Apron Toe Penny Loafer. Color Cognac. Low Stock. On sale for $84.91. MSRP $129.99.. 3.8 out of 5 stars

1 left in stock

Tan Thomas & Vine Bishop Apron Toe Penny Loafer

Tan Thomas & Vine Bishop Apron Toe Penny Loafer

Brand Name: Thomas & Vine
Product Name: Bishop Apron Toe Penny Loafer
Gender: Men's
Color: Cognac
Price: $84.91MSRP: $129.99
Rating: 4Rated 4 stars out of 5(10)

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

Stacy Adams - Marlowe Penny Slip-On Loafer. Color Cognac Leather. On sale for $89.37. MSRP $114.95.. 4.6 out of 5 stars

Brown Stacy Adams Marlowe Penny Slip-On Loafer

Brown Stacy Adams Marlowe Penny Slip-On Loafer

+3

Brand Name: Stacy Adams
Product Name: Marlowe Penny Slip-On Loafer
Gender: Men's
Color: Cognac Leather
Price: $89.37MSRP: $114.95
Rating: 5Rated 5 stars out of 5(28)

Tommy Hilfiger - Amile. Color Black. On sale for $51.00. MSRP $59.95.. 4.5 out of 5 stars

Black Tommy Hilfiger Amile

Black Tommy Hilfiger Amile

+3

Brand Name: Tommy Hilfiger
Product Name: Amile
Gender: Men's
Color: Black
Price: $51.00MSRP: $59.95
Rating: 5Rated 5 stars out of 5(4)

Tommy Hilfiger - Tabaro. Color Cognac. $69.95.

Tan Tommy Hilfiger Tabaro

Tan Tommy Hilfiger Tabaro

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

Floafers - Floafers Country Club Driver. Color Cypress/Gum. On sale for $35.49. MSRP $49.99.. 4.3 out of 5 stars

Green Floafers Floafers Country Club Driver

Green Floafers Floafers Country Club Driver

+4

Brand Name: Floafers
Product Name: Floafers Country Club Driver
Gender: Men's
Color: Cypress/Gum
Price: $35.49MSRP: $49.99
Rating: 4Rated 4 stars out of 5(30)

Tommy Hilfiger - Simol. Color Black. On sale for $59.40. MSRP $69.95.. 3.0 out of 5 stars

Black Tommy Hilfiger Simol

Black Tommy Hilfiger Simol

+2

Brand Name: Tommy Hilfiger
Product Name: Simol
Gender: Men's
Color: Black
Price: $59.40MSRP: $69.95
Rating: 3Rated 3 stars out of 5(2)

TOMS - Baja. Color Moonlight Blue. Low Stock. $54.90. 3.9 out of 5 stars

2 left in stock

Blue TOMS Baja

Blue TOMS Baja

+7

Brand Name: TOMS
Product Name: Baja
Gender: Men's
Color: Moonlight Blue
Price: $54.90
Rating: 4Rated 4 stars out of 5(94)

Rockport - Modern Prep Penny. Color Burgundy. On sale for $82.40. 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
Gender: Men's
Color: Burgundy
Price: $82.40MSRP: $119.95
Rating: 4Rated 4 stars out of 5(191)

Marc Joseph New York - Milford Ave. Color Havana Grainy. On sale for $85.14. 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: $85.14MSRP: $165.00
Rating: 5Rated 5 stars out of 5(1)

Rockport - TruFlex DresSports Penny. Color Dark Brown. On sale for $79.95. MSRP $119.95.. 5.0 out of 5 stars

Brown Rockport TruFlex DresSports Penny

Brown Rockport TruFlex DresSports Penny

+4

Brand Name: Rockport
Product Name: TruFlex DresSports Penny
Gender: Men's
Color: Dark Brown
Price: $79.95MSRP: $119.95
Rating: 5Rated 5 stars out of 5(2)

Dockers - Vaughn. Color Navy. On sale for $63.01. MSRP $85.00..

Navy Dockers Vaughn

Navy Dockers Vaughn

+2

Brand Name: Dockers
Product Name: Vaughn
Gender: Men's
Color: Navy
Price: $63.01MSRP: $85.00
Rating

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)

Tommy Hilfiger - Dime. Color Cognac. $69.95.

Tan Tommy Hilfiger Dime

Tan Tommy Hilfiger Dime

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

Steve Madden - Ramsee. Color Taupe Suede. On sale for $79.32. MSRP $120.00.. 3.8 out of 5 stars

Taupe Steve Madden Ramsee

Taupe Steve Madden Ramsee

+4

Brand Name: Steve Madden
Product Name: Ramsee
Gender: Men's
Color: Taupe Suede
Price: $79.32MSRP: $120.00
Rating: 4Rated 4 stars out of 5(10)

Carlos by Carlos Santana - Ritchie Driver Loafer. Color Olive Calf Nubuck. Low Stock. On sale for $76.99. 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: $76.99MSRP: $88.95
Rating: 4Rated 4 stars out of 5(7)

Johnston & Murphy - Emmett Penny. Color Dark Tan Full Grain. Low Stock. $99.90.

1 left in stock

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

Johnston & Murphy Collection - Damon Penny. Color Black Italian Calfskin. Low Stock. On sale for $95.11. MSRP $195.00..

6 left in stock

Black Johnston & Murphy Collection Damon Penny

Black Johnston & Murphy Collection Damon Penny

+2

Brand Name: Johnston & Murphy Collection
Product Name: Damon Penny
Gender: Men's
Color: Black Italian Calfskin
Price: $95.11MSRP: $195.00
Rating

Vagabond Shoemakers - Alex Suede Penny Loafer. Color Java Suede. Low Stock. On sale for $95.00. MSRP $190.00.. 5.0 out of 5 stars

4 left in stock

Black Vagabond Shoemakers Alex Suede Penny Loafer

Black Vagabond Shoemakers Alex Suede Penny Loafer

Brand Name: Vagabond Shoemakers
Product Name: Alex Suede Penny Loafer
Gender: Men's
Color: Java Suede
Price: $95.00MSRP: $190.00
Rating: 5Rated 5 stars out of 5(1)

Florsheim - Central Moc Toe Penny Leather. Color Cognac Smooth Leather. On sale for $79.95. MSRP $105.00.. 4.4 out of 5 stars

Tan Florsheim Central Moc Toe Penny Leather

Tan Florsheim Central Moc Toe Penny Leather

+2

Brand Name: Florsheim
Product Name: Central Moc Toe Penny Leather
Gender: Men's
Color: Cognac Smooth Leather
Price: $79.95MSRP: $105.00
Rating: 4Rated 4 stars out of 5(62)

Steve Madden - Bentin. Color Tobacco Suede. Low Stock. On sale for $89.97. MSRP $135.00..

4 left in stock

Brown Steve Madden Bentin

Brown Steve Madden Bentin

+2

Brand Name: Steve Madden
Product Name: Bentin
Gender: Men's
Color: Tobacco Suede
Price: $89.97MSRP: $135.00
Rating

Steve Madden - Ewald. Color Navy Fabric. $94.60.

Blue Steve Madden Ewald

Blue Steve Madden Ewald

Brand Name: Steve Madden
Product Name: Ewald
Gender: Men's
Color: Navy Fabric
Price: $94.60
Rating

Thomas & Vine - Watkins Embossed Penny Loafer. Color Cognac. Low Stock. On sale for $99.99. MSRP $149.99.. 2.5 out of 5 stars

7 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: $99.99MSRP: $149.99
Rating: 3Rated 3 stars out of 5(6)

Marc Joseph New York - Washington. Color Brown Napa. Low Stock. On sale for $96.71. MSRP $195.00.. 4.4 out of 5 stars

1 left in stock

Brown Marc Joseph New York Washington

Brown Marc Joseph New York Washington

+2

Brand Name: Marc Joseph New York
Product Name: Washington
Gender: Men's
Color: Brown Napa
Price: $96.71MSRP: $195.00
Rating: 4Rated 4 stars out of 5(5)

Get on the List

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