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

Penny Keeper Casual Comfort Shoes

51 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(430)

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(147)

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)

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)

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)

Eastland 1955 Edition - Classic II. Color Black Leather. On sale for $87.68. 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: $87.68MSRP: $100.00
Rating: 4Rated 4 stars out of 5(185)

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

White Kork-Ease Carlisle

White Kork-Ease Carlisle

+2

Brand Name: Kork-Ease
Product Name: Carlisle
Color: White
Price: $160.00
Rating: 4Rated 4 stars out of 5(38)

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)

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
Color: Dark Brown
Price: $110.00
Rating: 4Rated 4 stars out of 5(40)

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)

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 - Nerina. Color Navy. $125.00. 4.0 out of 5 stars

Navy Born Nerina

Navy Born Nerina

+3

Brand Name: Born
Product Name: Nerina
Color: Navy
Price: $125.00
Rating: 4Rated 4 stars out of 5(92)

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

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(44)

PIKOLINOS - Aldaya W8J-3541. Color Black. $179.95. 4.0 out of 5 stars

Black PIKOLINOS Aldaya W8J-3541

Black PIKOLINOS Aldaya W8J-3541

+2

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

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)

PIKOLINOS - Aldaya W8J-3541C2. Color Marfil. $179.95. 4.3 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(24)

Dr. Scholl's - Nice Day. Color Black Synthetic. On sale for $75.83. MSRP $100.00.. 3.7 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: $75.83MSRP: $100.00
Rating: 4Rated 4 stars out of 5(6)

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

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)

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)

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)

PIKOLINOS - Avila M1T-3205. Color Cuero. Low Stock. $189.95. 5.0 out of 5 stars

5 left in stock

Tan PIKOLINOS Avila M1T-3205

Tan PIKOLINOS Avila M1T-3205

+2

Brand Name: PIKOLINOS
Product Name: Avila M1T-3205
Color: Cuero
Price: $189.95
Rating: 5Rated 5 stars out of 5(1)

. Born - Marlo. Color Dark Brown. $134.95.

Brown Born Marlo

Brown Born Marlo

Brand Name: Born
Product Name: Marlo
Color: Dark Brown
Price: $134.95
Rating

Samuel Hubbard - Free Spirit For Her. Color Stonewashed Blue Suede/Gum Sole. Low Stock. $175.00. 4.2 out of 5 stars

8 left in stock

Blue Samuel Hubbard Free Spirit For Her

Blue Samuel Hubbard Free Spirit For Her

+5

Brand Name: Samuel Hubbard
Product Name: Free Spirit For Her
Color: Stonewashed Blue Suede/Gum Sole
Price: $175.00
Rating: 4Rated 4 stars out of 5(21)

Naturalizer - SOUL Naturalizer - Nova. Color Burgundy Synthetic. On sale for $68.18. MSRP $99.99.. 3.5 out of 5 stars

Burgundy Naturalizer SOUL Naturalizer - Nova

Burgundy Naturalizer SOUL Naturalizer - Nova

Brand Name: Naturalizer
Product Name: SOUL Naturalizer - Nova
Color: Burgundy Synthetic
Price: $68.18MSRP: $99.99
Rating: 3Rated 3 stars out of 5(11)

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)

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
Color: New Dress Blues
Price: $73.17MSRP: $119.95
Rating: 5Rated 5 stars out of 5(2)

SAS - Woodlawn. Color Mahogany. Low Stock. On sale for $195.01. MSRP $234.95.. 3.0 out of 5 stars

6 left in stock

Mahogany SAS Woodlawn

Mahogany SAS Woodlawn

Brand Name: SAS
Product Name: Woodlawn
Color: Mahogany
Price: $195.01MSRP: $234.95
Rating: 3Rated 3 stars out of 5(6)

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)

Vaneli - Adebel. Color Fushia/Blush Nappa. Low Stock. On sale for $130.46. MSRP $150.00..

7 left in stock

Pink Vaneli Adebel

Pink Vaneli Adebel

+2

Brand Name: Vaneli
Product Name: Adebel
Color: Fushia/Blush Nappa
Price: $130.46MSRP: $150.00
Rating

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(3)

Rockport - Susana Penny. Color Sand Leather. On sale for $80.37. MSRP $119.95.. 3.8 out of 5 stars

Beige Rockport Susana Penny

Beige Rockport Susana Penny

+2

Brand Name: Rockport
Product Name: Susana Penny
Color: Sand Leather
Price: $80.37MSRP: $119.95
Rating: 4Rated 4 stars out of 5(6)

ECCO - Modtray Penny Loafer. Color Cognac. On sale for $131.84. MSRP $179.95.. 3.8 out of 5 stars

Tan ECCO Modtray Penny Loafer

Tan ECCO Modtray Penny Loafer

+3

Brand Name: ECCO
Product Name: Modtray Penny Loafer
Color: Cognac
Price: $131.84MSRP: $179.95
Rating: 4Rated 4 stars out of 5(32)

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

9 left in stock

Burgundy Rockport Modern Prep Penny

Burgundy Rockport Modern Prep Penny

+2 colors/patterns

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

Vaneli - Zayna. Color Black Milled Calf. Low Stock. On sale for $166.20. MSRP $175.00.. 3.6 out of 5 stars

8 left in stock

Black Vaneli Zayna

Black Vaneli Zayna

Brand Name: Vaneli
Product Name: Zayna
Color: Black Milled Calf
Price: $166.20MSRP: $175.00
Rating: 4Rated 4 stars out of 5(5)

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

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

5 left in stock

Pink Gabor Gabor 25.213

Pink Gabor Gabor 25.213

+3

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

ECCO - Felicia Penny Loafer. Color Marine. On sale for $109.99. MSRP $140.00.. 4.2 out of 5 stars

Blue ECCO Felicia Penny Loafer

Blue ECCO Felicia Penny Loafer

Brand Name: ECCO
Product Name: Felicia Penny Loafer
Color: Marine
Price: $109.99MSRP: $140.00
Rating: 4Rated 4 stars out of 5(12)

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)

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

Brand Name: SAS
Product Name: Classic Slip On Comfort Loafer
Color: Navy
Price: $148.95
Rating: 4Rated 4 stars out of 5(144)

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)

Vaneli - Assia. Color Black Suede Combo. Low Stock. $144.95. 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: $144.95
Rating: 5Rated 5 stars out of 5(8)

Vaneli - Kimmo. Color Tobacco Nival Suede. On sale for $120.72. 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: $120.72MSRP: $175.00
Rating: 2Rated 2 stars out of 5(2)

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
Color: Brown Full Grain Leather
Price: $109.20MSRP: $120.00
Rating: 4Rated 4 stars out of 5(5)

Walking Cradles - Winnie 2. Color Navy Crinkle Patent. Low Stock. $149.45. 4.0 out of 5 stars

1 left in stock

Black Walking Cradles Winnie 2

Black Walking Cradles Winnie 2

+4

Brand Name: Walking Cradles
Product Name: Winnie 2
Color: Navy Crinkle Patent
Price: $149.45
Rating: 4Rated 4 stars out of 5(42)

Walking Cradles - Dannon. Color Black Holographic Plaid/Black Patent. Low Stock. On sale for $106.88. MSRP $154.95.. 4.0 out of 5 stars

3 left in stock

Multi Walking Cradles Dannon

Multi Walking Cradles Dannon

+2

Brand Name: Walking Cradles
Product Name: Dannon
Color: Black Holographic Plaid/Black Patent
Price: $106.88MSRP: $154.95
Rating: 4Rated 4 stars out of 5(45)

Eastland 1955 Edition - HOLLY. Color Black. On sale for $60.00. MSRP $65.00.. 3.9 out of 5 stars

Black Eastland 1955 Edition HOLLY

Black Eastland 1955 Edition HOLLY

Brand Name: Eastland 1955 Edition
Product Name: HOLLY
Color: Black
Price: $60.00MSRP: $65.00
Rating: 4Rated 4 stars out of 5(8)

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)

Deer Stags - Civic Comfort Penny Loafer. Color Brown. Low Stock. On sale for $43.54. MSRP $90.00..

8 left in stock

Brown Deer Stags Civic Comfort Penny Loafer

Brown Deer Stags Civic Comfort Penny Loafer

Brand Name: Deer Stags
Product Name: Civic Comfort Penny Loafer
Color: Brown
Price: $43.54MSRP: $90.00
Rating

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)

Josef Seibel - Sienna 96. Color Ocean Washed. Low Stock. $145.00. 4.4 out of 5 stars

2 left in stock

Black Josef Seibel Sienna 96

Black Josef Seibel Sienna 96

Brand Name: Josef Seibel
Product Name: Sienna 96
Color: Ocean Washed
Price: $145.00
Rating: 4Rated 4 stars out of 5(31)

Get on the List

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