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

Penny Keeper Leather Comfort Comfort Shoes

57 items found

Sort By

Your Selections

Search Results

. VIONIC - Cheryl II. Color Navy Blazer Leather. $130.00. 3.9 out of 5 stars

Navy VIONIC Cheryl II

Navy VIONIC Cheryl II

+4

Brand Name: VIONIC
Product Name: Cheryl II
Gender: Women's
Color: Navy Blazer Leather
Price: $130.00
Rating: 4Rated 4 stars out of 5(132)

. VIONIC - Uptown. Color Ivory Multi Leather. $120.00. 4.2 out of 5 stars

Beige VIONIC Uptown

Beige VIONIC Uptown

+13

Brand Name: VIONIC
Product Name: Uptown
Gender: Women's
Color: Ivory Multi Leather
Price: $120.00
Rating: 4Rated 4 stars out of 5(284)

Florsheim - Berkley Flex Penny Loafer. Color Brown Crazy Horse. $124.95. 4.2 out of 5 stars

Brown Florsheim Berkley Flex Penny Loafer

Brown Florsheim Berkley Flex Penny Loafer

+5

Brand Name: Florsheim
Product Name: Berkley Flex Penny Loafer
Gender: Men's
Color: Brown Crazy Horse
Price: $124.95
Rating: 4Rated 4 stars out of 5(144)

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)

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(12)

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(89)

Nunn Bush - Lincoln Penny Loafer. Color Black Polished. On sale for $64.95. MSRP $95.00.. 4.2 out of 5 stars

Black Nunn Bush Lincoln Penny Loafer

Black Nunn Bush Lincoln Penny Loafer

+2 colors/patterns

Brand Name: Nunn Bush
Product Name: Lincoln Penny Loafer
Gender: Men's
Color: Black Polished
Price: $64.95MSRP: $95.00
Rating: 4Rated 4 stars out of 5(293)

Florsheim - Sorrento Moc Toe Penny Loafer. Color Black Smooth. $129.95. 4.3 out of 5 stars

Black Florsheim Sorrento Moc Toe Penny Loafer

Black Florsheim Sorrento Moc Toe Penny Loafer

+2

Brand Name: Florsheim
Product Name: Sorrento Moc Toe Penny Loafer
Gender: Men's
Color: Black Smooth
Price: $129.95
Rating: 4Rated 4 stars out of 5(40)

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
Gender: Women's
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
Gender: Women's
Color: Camel
Price: $79.95MSRP: $100.00
Rating: 4Rated 4 stars out of 5(99)

ECCO - Dress Classic 15 Penny Loafer. Color Black/Limestone/Cognac. On sale for $112.51. MSRP $150.00.. 4.3 out of 5 stars

Black ECCO Dress Classic 15 Penny Loafer

Black ECCO Dress Classic 15 Penny Loafer

+5

Brand Name: ECCO
Product Name: Dress Classic 15 Penny Loafer
Gender: Women's
Color: Black/Limestone/Cognac
Price: $112.51MSRP: $150.00
Rating: 4Rated 4 stars out of 5(17)

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)

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
Gender: Men's
Color: Brown
Price: $79.95MSRP: $100.00
Rating: 4Rated 4 stars out of 5(62)

Vaneli - Adrik. Color Beige Crunch. $149.95. 4.6 out of 5 stars

Beige Vaneli Adrik

Beige Vaneli Adrik

Brand Name: Vaneli
Product Name: Adrik
Gender: Women's
Color: Beige Crunch
Price: $149.95
Rating: 5Rated 5 stars out of 5(9)

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)

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

8 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
Gender: Men's
Color: Black
Price: $79.95MSRP: $100.00
Rating: 5Rated 5 stars out of 5(7)

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

9 left in stock

Tan PIKOLINOS Aldaya W8J-3541

Tan PIKOLINOS Aldaya W8J-3541

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

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
Gender: Men's
Color: Black
Price: $129.95
Rating: 5Rated 5 stars out of 5(8)

Eastland 1955 Edition - Classic II. Color Black Leather. On sale for $88.88. 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
Gender: Women's
Color: Black Leather
Price: $88.88MSRP: $100.00
Rating: 4Rated 4 stars out of 5(185)

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

+2

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)

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

Brown ECCO Felicia Penny Loafer

Brown ECCO Felicia Penny Loafer

+2 colors/patterns

Brand Name: ECCO
Product Name: Felicia Penny Loafer
Gender: Women's
Color: Potting Soil
Price: $109.99MSRP: $140.00
Rating: 4Rated 4 stars out of 5(12)

Spring Step - Audette. Color Blue. $109.95. 1.0 out of 5 stars

Blue Spring Step Audette

Blue Spring Step Audette

+4

Brand Name: Spring Step
Product Name: Audette
Gender: Women's
Color: Blue
Price: $109.95
Rating: 1Rated 1 star out of 5(1)

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)

Spring Step - Capitola. Color Bone. $129.95.

Bone Spring Step Capitola

Bone Spring Step Capitola

+3

Brand Name: Spring Step
Product Name: Capitola
Gender: Women's
Color: Bone
Price: $129.95
Rating

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

+3

Brand Name: Rockport
Product Name: TruFlex DresSports Penny
Gender: Men's
Color: New Dress Blues
Price: $79.99MSRP: $119.95
Rating: 5Rated 5 stars out of 5(2)

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
Gender: Women's
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
Gender: Men's
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
Gender: Women's
Color: Stone
Price: $129.95
Rating: 4Rated 4 stars out of 5(1)

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

+3

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

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

Beige Born Holliston

Beige Born Holliston

Brand Name: Born
Product Name: Holliston
Gender: Women's
Color: Natural
Price: $135.00
Rating: 4Rated 4 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

+2

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

Rockport - Susana Penny. Color White Leather. Low Stock. On sale for $50.38. MSRP $119.95.. 3.8 out of 5 stars

9 left in stock

White Rockport Susana Penny

White Rockport Susana Penny

+3

Brand Name: Rockport
Product Name: Susana Penny
Gender: Women's
Color: White Leather
Price: $50.38MSRP: $119.95
Rating: 4Rated 4 stars out of 5(6)

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
Gender: Women's
Color: Upgrade Black
Price: $140.00
Rating: 4Rated 4 stars out of 5(262)

Vaneli - Zayna. Color Black Milled Calf. Low Stock. $174.95. 3.6 out of 5 stars

3 left in stock

Black Vaneli Zayna

Black Vaneli Zayna

+2

Brand Name: Vaneli
Product Name: Zayna
Gender: Women's
Color: Black Milled Calf
Price: $174.95
Rating: 4Rated 4 stars out of 5(5)

Allen Edmonds - Randolph. Color Walnut. $425.00. 4.0 out of 5 stars

Brown Allen Edmonds Randolph

Brown Allen Edmonds Randolph

+2

Brand Name: Allen Edmonds
Product Name: Randolph
Gender: Men's
Color: Walnut
Price: $425.00
Rating: 4Rated 4 stars out of 5(32)

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
Gender: Men's
Color: Black Calf
Price: $425.00
Rating: 3Rated 3 stars out of 5(9)

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
Gender: Women's
Color: Black Dublin
Price: $274.95
Rating: 3Rated 3 stars out of 5(4)

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
Gender: Women's
Color: Brown
Price: $185.00
Rating: 4Rated 4 stars out of 5(10)

La Canadienne - Lorne. Color Biscotti Suede. $425.00.

Gold La Canadienne Lorne

Gold La Canadienne Lorne

Brand Name: La Canadienne
Product Name: Lorne
Gender: Men's
Color: Biscotti Suede
Price: $425.00
Rating

SAS - Woodlawn. Color Mahogany. On sale for $96.33. MSRP $234.95.. 3.0 out of 5 stars

Mahogany SAS Woodlawn

Mahogany SAS Woodlawn

Brand Name: SAS
Product Name: Woodlawn
Gender: Men's
Color: Mahogany
Price: $96.33MSRP: $234.95
Rating: 3Rated 3 stars out of 5(6)

Rockport - Modern Prep Penny. Color Burgundy. On sale for $99.99. 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: $99.99MSRP: $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
Gender: Women's
Color: Black
Price: $175.00
Rating: 3Rated 3 stars out of 5(13)

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
Gender: Women's
Color: Tobacco Nival Suede
Price: $122.44MSRP: $175.00
Rating: 2Rated 2 stars out of 5(2)

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

3 left in stock

Brown Walking Cradles Dannon

Brown Walking Cradles Dannon

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

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

4 left in stock

Tan PIKOLINOS Avila M1T-3205

Tan PIKOLINOS Avila M1T-3205

+2

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

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

3 left in stock

White La Canadienne Richie

White La Canadienne Richie

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

Josef Seibel - Sienna 96. Color Ocean Washed. Low Stock. $145.00. 4.3 out of 5 stars

2 left in stock

Black Josef Seibel Sienna 96

Black Josef Seibel Sienna 96

+2

Brand Name: Josef Seibel
Product Name: Sienna 96
Gender: Women's
Color: Ocean Washed
Price: $145.00
Rating: 4Rated 4 stars out of 5(30)

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
Gender: Men's
Color: Mahogany Full Grain
Price: $145.00
Rating: 5Rated 5 stars out of 5(76)

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)

Mephisto - Kurtis. Color Black Hopper. Low Stock. $388.95. 1.0 out of 5 stars

2 left in stock

Black Mephisto Kurtis

Black Mephisto Kurtis

+2

Brand Name: Mephisto
Product Name: Kurtis
Gender: Men's
Color: Black Hopper
Price: $388.95
Rating: 1Rated 1 star out of 5(1)

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
Gender: Women's
Color: Navy
Price: $148.95
Rating: 4Rated 4 stars out of 5(142)

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
Gender: Women's
Color: Biscotti suede-274
Price: $425.00
Rating: 5Rated 5 stars out of 5(1)

Allen Edmonds - Randolph Sneaker. Color Chili. $300.00. 4.3 out of 5 stars

Brown Allen Edmonds Randolph Sneaker

Brown Allen Edmonds Randolph Sneaker

Brand Name: Allen Edmonds
Product Name: Randolph Sneaker
Gender: Men's
Color: Chili
Price: $300.00
Rating: 4Rated 4 stars out of 5(49)

Rockport Works - Top Shore. Color Black. Low Stock. $142.99. 3.5 out of 5 stars

4 left in stock

Black Rockport Works Top Shore

Black Rockport Works Top Shore

Brand Name: Rockport Works
Product Name: Top Shore
Gender: Women's
Color: Black
Price: $142.99
Rating: 4Rated 4 stars out of 5(22)

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
Gender: Women's
Color: Pink
Price: $62.70MSRP: $209.00
Rating: 5Rated 5 stars out of 5(3)

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

6 left in stock

Black Mephisto Alexis

Black Mephisto Alexis

+2

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

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
Gender: Men's
Color: Brown Full Grain Leather
Price: $120.00
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.