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

Size 10.5 Penny Keeper Shoes

50 items found

Sort By

Your Selections

Search Results

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
Color: Dark Brown
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(13)

Cole Haan - Grand Laser Penny Driver. Color British Tan/Java. On sale for $93.74. 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
Color: British Tan/Java
Price: $93.74MSRP: $155.00
Rating: 4Rated 4 stars out of 5(68)

Cole Haan - Wyatt Penny Driver. Color British Tan/Nicotine. On sale for $120.00. MSRP $125.00.. 4.3 out of 5 stars

Brown Cole Haan Wyatt Penny Driver

Brown Cole Haan Wyatt Penny Driver

+5

Brand Name: Cole Haan
Product Name: Wyatt Penny Driver
Color: British Tan/Nicotine
Price: $120.00MSRP: $125.00
Rating: 4Rated 4 stars out of 5(276)

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
Color: Black Smooth
Price: $89.95MSRP: $125.00
Rating: 4Rated 4 stars out of 5(89)

Marc Joseph New York - Nebraska. Color Tan Napa. On sale for $79.95. MSRP $185.00.. 4.5 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
Color: Tan Napa
Price: $79.95MSRP: $185.00
Rating: 5Rated 5 stars out of 5(6)

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
Color: Burgundy Polished
Price: $64.95MSRP: $90.00
Rating: 4Rated 4 stars out of 5(293)

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
Color: Cognac
Price: $74.95MSRP: $100.00
Rating: 4Rated 4 stars out of 5(154)

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)

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)

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 - Pinch Prep Penny Loafer. Color Black Brushoff. On sale for $112.00. MSRP $227.95.. 3.5 out of 5 stars

Black Cole Haan Pinch Prep Penny Loafer

Black Cole Haan Pinch Prep Penny Loafer

+4

Brand Name: Cole Haan
Product Name: Pinch Prep Penny Loafer
Color: Black Brushoff
Price: $112.00MSRP: $227.95
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
Color: Black
Price: $79.95MSRP: $100.00
Rating: 5Rated 5 stars out of 5(7)

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)

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
Color: Black
Price: $59.40MSRP: $69.95
Rating: 3Rated 3 stars out of 5(2)

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

5 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 - East Village Mens. Color Black Napa. Low Stock. On sale for $115.50. MSRP $175.00..

8 left in stock

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

Cole Haan - Pinch Weekender Penny. Color Sesame/Angora. On sale for $79.95. 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: $79.95MSRP: $120.00
Rating: 4Rated 4 stars out of 5(3)

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

Cole Haan - American Classics Pinch Penny Loafer. Color Navy Blazer/Angora/Dark Chocolate. On sale for $159.60. MSRP $228.00.. 4.0 out of 5 stars

Navy Cole Haan American Classics Pinch Penny Loafer

Navy Cole Haan American Classics Pinch Penny Loafer

+2

Brand Name: Cole Haan
Product Name: American Classics Pinch Penny Loafer
Color: Navy Blazer/Angora/Dark Chocolate
Price: $159.60MSRP: $228.00
Rating: 4Rated 4 stars out of 5(24)

Cole Haan - Pinch Weekender Penny Textured. Color Dark Chocolate Pebble/Ivory. On sale for $93.00. MSRP $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
Color: Dark Chocolate Pebble/Ivory
Price: $93.00MSRP: $100.00
Rating: 4Rated 4 stars out of 5(2)

Rockport - TruFlex DresSports Penny. Color New Dress Blues. On sale for $79.99. 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: $79.99MSRP: $119.95
Rating: 5Rated 5 stars out of 5(2)

ALDO - Legolas. Color Other Brown. Low Stock. On sale for $118.99. MSRP $128.00..

7 left in stock

Brown ALDO Legolas

Brown ALDO Legolas

+2

Brand Name: ALDO
Product Name: Legolas
Color: Other Brown
Price: $118.99MSRP: $128.00
Rating

Bruno Magli - Nathan. Color Rust Calf. On sale for $223.50. MSRP $298.00.. 4.3 out of 5 stars

Orange Bruno Magli Nathan

Orange Bruno Magli Nathan

Brand Name: Bruno Magli
Product Name: Nathan
Color: Rust Calf
Price: $223.50MSRP: $298.00
Rating: 4Rated 4 stars out of 5(6)

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
Color: Black
Price: $49.95MSRP: $70.00
Rating: 5Rated 5 stars out of 5(1)

Stacy Adams - Marlowe Penny Slip-On Loafer. Color Cognac Leather. On sale for $93.20. 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
Color: Cognac Leather
Price: $93.20MSRP: $114.95
Rating: 5Rated 5 stars out of 5(28)

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)

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)

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

Brown Tommy Hilfiger Amile

Brown Tommy Hilfiger Amile

+3

Brand Name: Tommy Hilfiger
Product Name: Amile
Color: Dark Brown
Price: $51.00MSRP: $59.95
Rating: 5Rated 5 stars out of 5(4)

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)

Bruno Magli - Silas. Color Navy Suede. Low Stock. On sale for $223.50. MSRP $298.00.. 2.8 out of 5 stars

9 left in stock

Blue Bruno Magli Silas

Blue Bruno Magli Silas

+4

Brand Name: Bruno Magli
Product Name: Silas
Color: Navy Suede
Price: $223.50MSRP: $298.00
Rating: 3Rated 3 stars out of 5(6)

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

Tommy Hilfiger - Tabaro. Color Cognac. On sale for $59.40. MSRP $69.95..

Tan Tommy Hilfiger Tabaro

Tan Tommy Hilfiger Tabaro

Brand Name: Tommy Hilfiger
Product Name: Tabaro
Color: Cognac
Price: $59.40MSRP: $69.95
Rating

Johnston & Murphy - Lewis Penny. Color Tan Full Grain Leather. Low Stock. On sale for $99.99. MSRP $149.00.. 4.2 out of 5 stars

1 left in stock

Tan Johnston & Murphy Lewis Penny

Tan Johnston & Murphy Lewis Penny

Brand Name: Johnston & Murphy
Product Name: Lewis Penny
Color: Tan Full Grain Leather
Price: $99.99MSRP: $149.00
Rating: 4Rated 4 stars out of 5(51)

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)

Marc Joseph New York - Lexington. Color Black Nappa Leather. Low Stock. On sale for $70.95. MSRP $195.00.. 4.2 out of 5 stars

1 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
Color: Black Nappa Leather
Price: $70.95MSRP: $195.00
Rating: 4Rated 4 stars out of 5(5)

Marc Joseph New York - Union Street 2. Color Tan Burnished Nappa. On sale for $108.50. MSRP $155.00.. 4.8 out of 5 stars

Tan Marc Joseph New York Union Street 2

Tan Marc Joseph New York Union Street 2

+3

Brand Name: Marc Joseph New York
Product Name: Union Street 2
Color: Tan Burnished Nappa
Price: $108.50MSRP: $155.00
Rating: 5Rated 5 stars out of 5(4)

Carlos by Carlos Santana - Ritchie Driver Loafer. Color Navy Calf Nubuck. Low Stock. On sale for $76.99. MSRP $88.95.. 3.7 out of 5 stars

4 left in stock

Navy Carlos by Carlos Santana Ritchie Driver Loafer

Navy Carlos by Carlos Santana Ritchie Driver Loafer

+2

Brand Name: Carlos by Carlos Santana
Product Name: Ritchie Driver Loafer
Color: Navy Calf Nubuck
Price: $76.99MSRP: $88.95
Rating: 4Rated 4 stars out of 5(7)

Bruno Magli - Maioco Penny. Color Cognac. Low Stock. On sale for $320.20. MSRP $395.00..

8 left in stock

Tan Bruno Magli Maioco Penny

+2

Brand Name: Bruno Magli
Product Name: Maioco Penny
Color: Cognac
Price: $320.20MSRP: $395.00
Rating

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

Sebago - Byron. Color Black. Low Stock. On sale for $71.75. MSRP $165.00..

7 left in stock

Black Sebago Byron

Black Sebago Byron

Brand Name: Sebago
Product Name: Byron
Color: Black
Price: $71.75MSRP: $165.00
Rating

Johnston & Murphy Collection - Damon Penny. Color Black Italian Calfskin. Low Stock. On sale for $130.65. MSRP $195.00..

7 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
Color: Black Italian Calfskin
Price: $130.65MSRP: $195.00
Rating

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

10 left in stock

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)

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)

Florsheim - Central Moc Toe Penny Leather. Color Brown Crazy Horse. On sale for $99.95. MSRP $105.00.. 4.4 out of 5 stars

Brown Florsheim Central Moc Toe Penny Leather

Brown Florsheim Central Moc Toe Penny Leather

+2

Brand Name: Florsheim
Product Name: Central Moc Toe Penny Leather
Color: Brown Crazy Horse
Price: $99.95MSRP: $105.00
Rating: 4Rated 4 stars out of 5(62)

Born - Taylor. Color Black Full Grain Leather. Low Stock. On sale for $78.00. MSRP $120.00.. 4.0 out of 5 stars

2 left in stock

Black Born Taylor

Black Born Taylor

+2

Brand Name: Born
Product Name: Taylor
Color: Black Full Grain Leather
Price: $78.00MSRP: $120.00
Rating: 4Rated 4 stars out of 5(5)

Allen Edmonds - Supersport Penny. Color Loden. Low Stock. On sale for $170.25. MSRP $295.00.. 3.6 out of 5 stars

8 left in stock

Green Allen Edmonds Supersport Penny

Green Allen Edmonds Supersport Penny

+4

Brand Name: Allen Edmonds
Product Name: Supersport Penny
Color: Loden
Price: $170.25MSRP: $295.00
Rating: 4Rated 4 stars out of 5(27)

Steve Madden - Bentin. Color Navy Suede. Low Stock. On sale for $129.02. MSRP $135.00..

4 left in stock

Blue Steve Madden Bentin

Blue Steve Madden Bentin

+2

Brand Name: Steve Madden
Product Name: Bentin
Color: Navy Suede
Price: $129.02MSRP: $135.00
Rating

Get on the List

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