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

Penny Keeper Casual Comfort Shoes

59 items found

Sort By

Your Selections

Search Results

VIONIC - Uptown. Color Camel Leather. $130.00. 4.3 out of 5 stars

Tan VIONIC Uptown

Tan VIONIC Uptown

+13

Brand Name: VIONIC
Product Name: Uptown
Color: Camel Leather
Price: $130.00
Rating: 4Rated 4 stars out of 5(381)

VIONIC - Cheryl II. Color Black Nappa. $135.00. 3.9 out of 5 stars

Black VIONIC Cheryl II

Black VIONIC Cheryl II

+4

Brand Name: VIONIC
Product Name: Cheryl II
Color: Black Nappa
Price: $135.00
Rating: 4Rated 4 stars out of 5(137)

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)

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)

Kork-Ease - Carlisle. Color Tan. $160.00. 3.9 out of 5 stars

Tan Kork-Ease Carlisle

Tan Kork-Ease Carlisle

+1

Brand Name: Kork-Ease
Product Name: Carlisle
Color: Tan
Price: $160.00
Rating: 4Rated 4 stars out of 5(37)

Eastland 1955 Edition - Patricia. Color Camel. On sale for $79.95. MSRP $100.00.. 3.6 out of 5 stars

Tan Eastland 1955 Edition Patricia

Tan Eastland 1955 Edition Patricia

+12

Brand Name: Eastland 1955 Edition
Product Name: Patricia
Color: Camel
Price: $79.95MSRP: $100.00
Rating: 4Rated 4 stars out of 5(100)

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)

Naturalizer - SOUL Naturalizer - Nova. Color Black Synthetic. On sale for $49.04. MSRP $109.99.. 3.5 out of 5 stars

Black Naturalizer SOUL Naturalizer - Nova

Black Naturalizer SOUL Naturalizer - Nova

Brand Name: Naturalizer
Product Name: SOUL Naturalizer - Nova
Color: Black Synthetic
Price: $49.04MSRP: $109.99
Rating: 3Rated 3 stars out of 5(11)

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

10 left in stock

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)

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)

Eastland 1955 Edition - Classic II. Color Black Leather. On sale for $88.94. MSRP $100.00.. 3.8 out of 5 stars

Black Eastland 1955 Edition Classic II

Black Eastland 1955 Edition Classic II

+5

Brand Name: Eastland 1955 Edition
Product Name: Classic II
Color: Black Leather
Price: $88.94MSRP: $100.00
Rating: 4Rated 4 stars out of 5(185)

Born - Nerina. Color Black Nubuck. $125.00. 4.0 out of 5 stars

Black Born Nerina

Black Born Nerina

+3

Brand Name: Born
Product Name: Nerina
Color: Black Nubuck
Price: $125.00
Rating: 4Rated 4 stars out of 5(89)

PIKOLINOS - Aldaya W8J-3541. Color Cuero. Low Stock. $179.95. 4.0 out of 5 stars

6 left in stock

Tan PIKOLINOS Aldaya W8J-3541

Tan PIKOLINOS Aldaya W8J-3541

+3

Brand Name: PIKOLINOS
Product Name: Aldaya W8J-3541
Color: Cuero
Price: $179.95
Rating: 4Rated 4 stars out of 5(29)

Born - Carrera. Color Black. Low Stock. $135.00. 4.4 out of 5 stars

7 left in stock

Black Born Carrera

Black Born Carrera

+5

Brand Name: Born
Product Name: Carrera
Color: Black
Price: $135.00
Rating: 4Rated 4 stars out of 5(42)

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)

ECCO - S Lite Moc Penny Loafer. Color Black. $169.59. 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
Color: Black
Price: $169.59
Rating: 4Rated 4 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
Color: Dark Tan Leather
Price: $89.99MSRP: $100.00
Rating: 2Rated 2 stars out of 5(17)

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)

Rockport - Kacey Penny. Color Black Patent. On sale for $69.99. MSRP $100.00.. 3.4 out of 5 stars

Black Rockport Kacey Penny

Black Rockport Kacey Penny

Brand Name: Rockport
Product Name: Kacey Penny
Color: Black Patent
Price: $69.99MSRP: $100.00
Rating: 3Rated 3 stars out of 5(47)

Samuel Hubbard - Free Spirit For Her. Color Luggage Tan Full Grain/White Topstitch/Gum Sole. Low Stock. $175.00. 4.2 out of 5 stars

6 left in stock

Brown Samuel Hubbard Free Spirit For Her

Brown Samuel Hubbard Free Spirit For Her

+7

Brand Name: Samuel Hubbard
Product Name: Free Spirit For Her
Color: Luggage Tan Full Grain/White Topstitch/Gum Sole
Price: $175.00
Rating: 4Rated 4 stars out of 5(21)

PIKOLINOS - Aldaya W8J-3541C2. Color Marfil. $179.95. 4.4 out of 5 stars

Beige PIKOLINOS Aldaya W8J-3541C2

Beige PIKOLINOS Aldaya W8J-3541C2

+2

Brand Name: PIKOLINOS
Product Name: Aldaya W8J-3541C2
Color: Marfil
Price: $179.95
Rating: 4Rated 4 stars out of 5(21)

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
Color: Tan Full Grain
Price: $120.00
Rating: 5Rated 5 stars out of 5(2)

Spring Step - Lexington. Color Stone. $129.95. 4.0 out of 5 stars

White Spring Step Lexington

White Spring Step Lexington

+4

Brand Name: Spring Step
Product Name: Lexington
Color: Stone
Price: $129.95
Rating: 4Rated 4 stars out of 5(1)

Spring Step - Capitola. Color Bone. $129.95.

Bone Spring Step Capitola

Bone Spring Step Capitola

+3

Brand Name: Spring Step
Product Name: Capitola
Color: Bone
Price: $129.95
Rating

ECCO - Felicia Penny Loafer. Color Marine. On sale for $106.27. MSRP $140.00.. 4.2 out of 5 stars

Blue ECCO Felicia Penny Loafer

Blue ECCO Felicia Penny Loafer

+2 colors/patterns

Brand Name: ECCO
Product Name: Felicia Penny Loafer
Color: Marine
Price: $106.27MSRP: $140.00
Rating: 4Rated 4 stars out of 5(12)

Dr. Scholl's - Nice Day. Color Black Synthetic. On sale for $53.00. MSRP $100.00.. 3.6 out of 5 stars

Black Dr. Scholl's Nice Day

Black Dr. Scholl's Nice Day

Brand Name: Dr. Scholl's
Product Name: Nice Day
Color: Black Synthetic
Price: $53.00MSRP: $100.00
Rating: 4Rated 4 stars out of 5(5)

Kork-Ease - Barbara. Color Brown. $185.00. 4.4 out of 5 stars

Brown Kork-Ease Barbara

Brown Kork-Ease Barbara

Brand Name: Kork-Ease
Product Name: Barbara
Color: Brown
Price: $185.00
Rating: 4Rated 4 stars out of 5(10)

Vaneli - Zayna. Color Black Milled Calf. Low Stock. On sale for $157.45. MSRP $175.00.. 3.6 out of 5 stars

5 left in stock

Black Vaneli Zayna

Black Vaneli Zayna

+2

Brand Name: Vaneli
Product Name: Zayna
Color: Black Milled Calf
Price: $157.45MSRP: $175.00
Rating: 4Rated 4 stars out of 5(5)

Vaneli - Kimmo. Color Tobacco Nival Suede. On sale for $122.44. MSRP $175.00.. 2.0 out of 5 stars

Brown Vaneli Kimmo

Brown Vaneli Kimmo

Brand Name: Vaneli
Product Name: Kimmo
Color: Tobacco Nival Suede
Price: $122.44MSRP: $175.00
Rating: 2Rated 2 stars out of 5(2)

Born - Holliston. Color Natural. $135.00. 4.0 out of 5 stars

Beige Born Holliston

Beige Born Holliston

Brand Name: Born
Product Name: Holliston
Color: Natural
Price: $135.00
Rating: 4Rated 4 stars out of 5(6)

FLY LONDON - TOKY803FLY. Color Black Dublin. Low Stock. $274.95. 3.2 out of 5 stars

7 left in stock

Black FLY LONDON TOKY803FLY

Black FLY LONDON TOKY803FLY

Brand Name: FLY LONDON
Product Name: TOKY803FLY
Color: Black Dublin
Price: $274.95
Rating: 3Rated 3 stars out of 5(4)

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)

ECCO - Modtray Penny Loafer. Color Black Leather. Low Stock. $179.95. 3.8 out of 5 stars

1 left in stock

Black ECCO Modtray Penny Loafer

Black ECCO Modtray Penny Loafer

+3

Brand Name: ECCO
Product Name: Modtray Penny Loafer
Color: Black Leather
Price: $179.95
Rating: 4Rated 4 stars out of 5(31)

Vaneli - Adebel. Color Navy/Sky Nappa. On sale for $97.46. MSRP $150.00..

Black Vaneli Adebel

Black Vaneli Adebel

+2

Brand Name: Vaneli
Product Name: Adebel
Color: Navy/Sky Nappa
Price: $97.46MSRP: $150.00
Rating

Walking Cradles - Winnie 2. Color Black Patent. Low Stock. On sale for $44.85. MSRP $149.50.. 4.0 out of 5 stars

7 left in stock

Black Walking Cradles Winnie 2

Black Walking Cradles Winnie 2

+3

Brand Name: Walking Cradles
Product Name: Winnie 2
Color: Black Patent
Price: $44.85MSRP: $149.50
Rating: 4Rated 4 stars out of 5(42)

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)

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

1 left in stock

Brown Johnston & Murphy Cort Penny

Brown Johnston & Murphy Cort Penny

+2

Brand Name: Johnston & Murphy
Product Name: Cort Penny
Color: Mahogany Full Grain
Price: $145.00
Rating: 5Rated 5 stars out of 5(76)

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)

Kork-Ease - Modeste. Color Black. $175.00. 3.2 out of 5 stars

Black Kork-Ease Modeste

Black Kork-Ease Modeste

Brand Name: Kork-Ease
Product Name: Modeste
Color: Black
Price: $175.00
Rating: 3Rated 3 stars out of 5(13)

Rockport - Susana Penny. Color Black Leather. On sale for $98.51. MSRP $119.95.. 3.8 out of 5 stars

Black Rockport Susana Penny

Black Rockport Susana Penny

+2

Brand Name: Rockport
Product Name: Susana Penny
Color: Black Leather
Price: $98.51MSRP: $119.95
Rating: 4Rated 4 stars out of 5(6)

Walking Cradles - Dannon. Color Brown Patent Croco. Low Stock. On sale for $46.49. MSRP $154.95.. 4.0 out of 5 stars

4 left in stock

Brown Walking Cradles Dannon

Brown Walking Cradles Dannon

Brand Name: Walking Cradles
Product Name: Dannon
Color: Brown Patent Croco
Price: $46.49MSRP: $154.95
Rating: 4Rated 4 stars out of 5(45)

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

5 left in stock

Black Mephisto Alexis

Black Mephisto Alexis

+2

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

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
Color: Black
Price: $189.95
Rating: 5Rated 5 stars out of 5(1)

Alegria - Taylor. Color Upgrade Black. $140.00. 3.8 out of 5 stars

Black Alegria Taylor

Black Alegria Taylor

Brand Name: Alegria
Product Name: Taylor
Color: Upgrade Black
Price: $140.00
Rating: 4Rated 4 stars out of 5(262)

La Canadienne - Richie. Color White Leather. Low Stock. On sale for $135.00. MSRP $450.00..

2 left in stock

White La Canadienne Richie

White La Canadienne Richie

Brand Name: La Canadienne
Product Name: Richie
Color: White Leather
Price: $135.00MSRP: $450.00
Rating

Gabor - Gabor 25.213. Color Pink. Low Stock. On sale for $62.70. MSRP $209.00.. 4.7 out of 5 stars

7 left in stock

Pink Gabor Gabor 25.213

Pink Gabor Gabor 25.213

+2

Brand Name: Gabor
Product Name: Gabor 25.213
Color: Pink
Price: $62.70MSRP: $209.00
Rating: 5Rated 5 stars out of 5(3)

Vaneli - Assia. Color Black Suede Combo. Low Stock. On sale for $101.50. MSRP $145.00.. 4.6 out of 5 stars

1 left in stock

Black Vaneli Assia

Black Vaneli Assia

Brand Name: Vaneli
Product Name: Assia
Color: Black Suede Combo
Price: $101.50MSRP: $145.00
Rating: 5Rated 5 stars out of 5(8)

SAS - Classic Slip On Comfort Loafer. Color Navy. $148.95. 4.1 out of 5 stars

Navy SAS Classic Slip On Comfort Loafer

Navy SAS Classic Slip On Comfort Loafer

+3

Brand Name: SAS
Product Name: Classic Slip On Comfort Loafer
Color: Navy
Price: $148.95
Rating: 4Rated 4 stars out of 5(142)

Josef Seibel - Sienna 96. Color Camel Washed. Low Stock. $150.00. 4.3 out of 5 stars

2 left in stock

Tan Josef Seibel Sienna 96

Tan Josef Seibel Sienna 96

Brand Name: Josef Seibel
Product Name: Sienna 96
Color: Camel Washed
Price: $150.00
Rating: 4Rated 4 stars out of 5(30)

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
Color: Cognac Smooth Leather
Price: $79.95MSRP: $105.00
Rating: 4Rated 4 stars out of 5(62)

Miz Mooz - Legend. Color Bordeaux Patent. Low Stock. $159.95. 4.2 out of 5 stars

1 left in stock

Brown Miz Mooz Legend

Brown Miz Mooz Legend

Brand Name: Miz Mooz
Product Name: Legend
Color: Bordeaux Patent
Price: $159.95
Rating: 4Rated 4 stars out of 5(6)

Born - Taylor. Color Brown Full Grain Leather. Low Stock. $120.00. 4.0 out of 5 stars

1 left in stock

Brown Born Taylor

Brown Born Taylor

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

Aerosoles - Penny Driver. Color Black Faux Suede. Low Stock. $89.00. 4.0 out of 5 stars

1 left in stock

Black Aerosoles Penny Driver

Black Aerosoles Penny Driver

Brand Name: Aerosoles
Product Name: Penny Driver
Color: Black Faux Suede
Price: $89.00
Rating: 4Rated 4 stars out of 5(2)

La Canadienne - Dominic. Color Biscotti suede-274. $425.00. 5.0 out of 5 stars

Brown La Canadienne Dominic

Brown La Canadienne Dominic

Brand Name: La Canadienne
Product Name: Dominic
Color: Biscotti suede-274
Price: $425.00
Rating: 5Rated 5 stars out of 5(1)

Eastland 1955 Edition - HOLLY. Color Brown. On sale for $53.71. MSRP $65.00.. 3.9 out of 5 stars

Brown Eastland 1955 Edition HOLLY

Brown Eastland 1955 Edition HOLLY

Brand Name: Eastland 1955 Edition
Product Name: HOLLY
Color: Brown
Price: $53.71MSRP: $65.00
Rating: 4Rated 4 stars out of 5(8)

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

LifeStride - Anna. Color Navy. Low Stock. $69.94. 3.7 out of 5 stars

1 left in stock

Navy LifeStride Anna

Navy LifeStride Anna

Brand Name: LifeStride
Product Name: Anna
Color: Navy
Price: $69.94
Rating: 4Rated 4 stars out of 5(27)

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)

Get on the List

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