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

Size 9.5 Penny Keeper Comfort Products

33 items found

Sort By

Your Selections

Search Results

Rockport - Classic Loafer Lite Penny. Color Black II. On sale for $79.95. MSRP $115.00. 30% off. 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
Gender: Men's
Color: Black II
Price: $79.95MSRP: $115.0030% OFF
Rating: 4Rated 4 stars out of 5(408)

Florsheim - Berkley Flex Penny Loafer. Color Brown Crazy Horse. On sale for $110.22. MSRP $125.00. 12% off. 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: $110.22MSRP: $125.0012% OFF
Rating: 4Rated 4 stars out of 5(191)

Florsheim - Throttle Penny. Color Black II. On sale for $79.95. MSRP $110.00. 27% off. 4.3 out of 5 stars

Black Florsheim Throttle Penny

Black Florsheim Throttle Penny

+2

Brand Name: Florsheim
Product Name: Throttle Penny
Gender: Men's
Color: Black II
Price: $79.95MSRP: $110.0027% OFF
Rating: 4Rated 4 stars out of 5(15)

Cole Haan - Pinch Prep Penny Loafer. Color Scotch. $112.00. 4.1 out of 5 stars

Brown Cole Haan Pinch Prep Penny Loafer

Brown Cole Haan Pinch Prep Penny Loafer

+8

Brand Name: Cole Haan
Product Name: Pinch Prep Penny Loafer
Gender: Men's
Color: Scotch
Price: $112.00
Rating: 4Rated 4 stars out of 5(8)

Polo Ralph Lauren - Alston Penny. Color Black. $178.00. 3.0 out of 5 stars

Black Polo Ralph Lauren Alston Penny

Black Polo Ralph Lauren Alston Penny

+5

Brand Name: Polo Ralph Lauren
Product Name: Alston Penny
Gender: Men's
Color: Black
Price: $178.00
Rating: 3Rated 3 stars out of 5(1)

Cole Haan - Pinch Weekender Penny Textured. Color British Tan/Ivory. On sale for $65.00. MSRP $90.00. 28% off. 4.5 out of 5 stars

Brown Cole Haan Pinch Weekender Penny Textured

Brown Cole Haan Pinch Weekender Penny Textured

+4

Brand Name: Cole Haan
Product Name: Pinch Weekender Penny Textured
Gender: Men's
Color: British Tan/Ivory
Price: $65.00MSRP: $90.0028% OFF
Rating: 5Rated 5 stars out of 5(4)

Johnston & Murphy - Hayes Penny Loafer. Color Black. On sale for $99.90. MSRP $135.00. 26% off. 4.0 out of 5 stars

Black Johnston & Murphy Hayes Penny Loafer

Black Johnston & Murphy Hayes Penny Loafer

+2

Brand Name: Johnston & Murphy
Product Name: Hayes Penny Loafer
Gender: Men's
Color: Black
Price: $99.90MSRP: $135.0026% OFF
Rating: 4Rated 4 stars out of 5(115)

Frye - Tyler Flex Penny. Color Caramel. $198.00. 3.5 out of 5 stars

Brown Frye Tyler Flex Penny

Brown Frye Tyler Flex Penny

+4

Brand Name: Frye
Product Name: Tyler Flex Penny
Gender: Men's
Color: Caramel
Price: $198.00
Rating: 4Rated 4 stars out of 5(2)

Nunn Bush - Noah Beef Roll Penny Loafer. Color Black. On sale for $79.95. MSRP $100.00. 20% off. 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: $79.95MSRP: $100.0020% OFF
Rating: 4Rated 4 stars out of 5(67)

Nunn Bush - Drexel Moc Toe Penny Loafer with KORE Walking Comfort Technology. Color Cognac. On sale for $69.99. MSRP $100.00. 30% off. 4.3 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: $69.99MSRP: $100.0030% OFF
Rating: 4Rated 4 stars out of 5(169)

Marc Joseph New York - Monaco. Color Cognac Grainy. On sale for $60.79. MSRP $185.00. 67% off.

Brown Marc Joseph New York Monaco

Brown Marc Joseph New York Monaco

+5

Brand Name: Marc Joseph New York
Product Name: Monaco
Gender: Men's
Color: Cognac Grainy
Price: $60.79MSRP: $185.0067% OFF
Rating

Florsheim - Midtown Penny Slip-On. Color Cognac Smooth. On sale for $89.95. MSRP $125.00. 28% off. 4.4 out of 5 stars

Neutral Florsheim Midtown Penny Slip-On

Neutral Florsheim Midtown Penny Slip-On

+2

Brand Name: Florsheim
Product Name: Midtown Penny Slip-On
Gender: Men's
Color: Cognac Smooth
Price: $89.95MSRP: $125.0028% OFF
Rating: 4Rated 4 stars out of 5(112)

COACH - Declan Loafer. Color Saddle. On sale for $150.00. MSRP $250.00. 40% off. 4.8 out of 5 stars

Brown COACH Declan Loafer

Brown COACH Declan Loafer

Brand Name: COACH
Product Name: Declan Loafer
Gender: Men's
Color: Saddle
Price: $150.00MSRP: $250.0040% OFF
Rating: 5Rated 5 stars out of 5(4)

ECCO - S Lite Moc Penny Loafer. Color Black. $174.95. 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: $174.95
Rating: 4Rated 4 stars out of 5(4)

Nunn Bush - Lincoln Penny Loafer. Color Burgundy Polished. On sale for $69.95. MSRP $95.00. 26% off. 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: $69.95MSRP: $95.0026% OFF
Rating: 4Rated 4 stars out of 5(312)

Florsheim - Sorrento Moc Toe Penny Loafer. Color Cognac Smooth. $129.95. 4.2 out of 5 stars

Neutral Florsheim Sorrento Moc Toe Penny Loafer

Neutral Florsheim Sorrento Moc Toe Penny Loafer

+2

Brand Name: Florsheim
Product Name: Sorrento Moc Toe Penny Loafer
Gender: Men's
Color: Cognac Smooth
Price: $129.95
Rating: 4Rated 4 stars out of 5(44)

Dockers - Colleague. Color Black. On sale for $49.00. MSRP $79.00. 38% off. 3.3 out of 5 stars

Black Dockers Colleague

Black Dockers Colleague

+3

Brand Name: Dockers
Product Name: Colleague
Gender: Men's
Color: Black
Price: $49.00MSRP: $79.0038% OFF
Rating: 3Rated 3 stars out of 5(3)

Allen Edmonds - Randolph 2.0 Slip-on Sneaker. Color Dark Chili Leather. On sale for $249.00. MSRP $325.00. 23% off. 3.5 out of 5 stars

Brown Allen Edmonds Randolph 2.0 Slip-on Sneaker

Brown Allen Edmonds Randolph 2.0 Slip-on Sneaker

+5

Brand Name: Allen Edmonds
Product Name: Randolph 2.0 Slip-on Sneaker
Gender: Men's
Color: Dark Chili Leather
Price: $249.00MSRP: $325.0023% OFF
Rating: 4Rated 4 stars out of 5(2)

Rockport - Liam. Color Black Leather. $129.95. 4.0 out of 5 stars

Black Rockport Liam

Black Rockport Liam

+1

Brand Name: Rockport
Product Name: Liam
Gender: Men's
Color: Black Leather
Price: $129.95
Rating: 4Rated 4 stars out of 5(2)

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

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)

Samuel Hubbard - Free Spirit for Him. Color Brown Leather. $195.00. 3.5 out of 5 stars

Brown Samuel Hubbard Free Spirit for Him

Brown Samuel Hubbard Free Spirit for Him

+2

Brand Name: Samuel Hubbard
Product Name: Free Spirit for Him
Gender: Men's
Color: Brown Leather
Price: $195.00
Rating: 4Rated 4 stars out of 5(4)

Florsheim - Zaffiro Moc Toe Penny Loafer. Color Black. On sale for $119.99. MSRP $130.00. 8% off. 4.7 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: $119.99MSRP: $130.008% OFF
Rating: 5Rated 5 stars out of 5(16)

SAS - Woodlawn. Color Licorice. On sale for $126.87. MSRP $234.95. 46% off. 3.0 out of 5 stars

Multi SAS Woodlawn

Multi SAS Woodlawn

Brand Name: SAS
Product Name: Woodlawn
Gender: Men's
Color: Licorice
Price: $126.87MSRP: $234.9546% OFF
Rating: 3Rated 3 stars out of 5(6)

Stacy Adams - Spencer Penny Slip-On. Color Tan. On sale for $84.00. MSRP $120.00. 30% off. 5.0 out of 5 stars

Tan Stacy Adams Spencer Penny Slip-On

Tan Stacy Adams Spencer Penny Slip-On

+4

Brand Name: Stacy Adams
Product Name: Spencer Penny Slip-On
Gender: Men's
Color: Tan
Price: $84.00MSRP: $120.0030% OFF
Rating: 5Rated 5 stars out of 5(4)

Bruno Magli - Maioco Penny. Color Black. $395.00.

Black Bruno Magli Maioco Penny

Black Bruno Magli Maioco Penny

+3

Brand Name: Bruno Magli
Product Name: Maioco Penny
Gender: Men's
Color: Black
Price: $395.00
Rating

Allen Edmonds - Randolph. Color Coffee. On sale for $402.98. MSRP $425.00. 5% off. 3.9 out of 5 stars

Brown Allen Edmonds Randolph

Brown Allen Edmonds Randolph

+2

Brand Name: Allen Edmonds
Product Name: Randolph
Gender: Men's
Color: Coffee
Price: $402.98MSRP: $425.005% OFF
Rating: 4Rated 4 stars out of 5(35)

Marc Joseph New York - East Village Mens. Color Whiskey Napa. Low Stock. On sale for $110.25. MSRP $175.00. 37% off.

Low Stock

Tan Marc Joseph New York East Village Mens

Tan Marc Joseph New York East Village Mens

Brand Name: Marc Joseph New York
Product Name: East Village Mens
Gender: Men's
Color: Whiskey Napa
Price: $110.25MSRP: $175.0037% OFF
Rating

Marc Joseph New York - River Road. Color Black Grainy. On sale for $69.95. MSRP $185.00. 62% off. 5.0 out of 5 stars

Black Marc Joseph New York River Road

Black Marc Joseph New York River Road

+3

Brand Name: Marc Joseph New York
Product Name: River Road
Gender: Men's
Color: Black Grainy
Price: $69.95MSRP: $185.0062% OFF
Rating: 5Rated 5 stars out of 5(1)

Bruno Magli - Raging Penny. Color Black. $395.00.

Black Bruno Magli Raging Penny

Black Bruno Magli Raging Penny

Brand Name: Bruno Magli
Product Name: Raging Penny
Gender: Men's
Color: Black
Price: $395.00
Rating

Born - Simon III. Color Tan Full Grain. $119.95. 3.3 out of 5 stars

Tan Born Simon III

Tan Born Simon III

Brand Name: Born
Product Name: Simon III
Gender: Men's
Color: Tan Full Grain
Price: $119.95
Rating: 3Rated 3 stars out of 5(3)

Allen Edmonds - Randolph. Color Black Calf. On sale for $329.00. MSRP $425.00. 23% off. 3.5 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: $329.00MSRP: $425.0023% OFF
Rating: 3Rated 3 stars out of 5(11)

ALDO - Legolas. Color Navy. Low Stock. On sale for $92.16. MSRP $128.00. 28% off.

Low Stock

Navy ALDO Legolas

Navy ALDO Legolas

+2

Brand Name: ALDO
Product Name: Legolas
Gender: Men's
Color: Navy
Price: $92.16MSRP: $128.0028% OFF
Rating

Cole Haan - American Classics Pinch Penny Loafer. Color Truffle/Natural. Low Stock. On sale for $205.20. MSRP $228.00. 10% off. 3.9 out of 5 stars

Low Stock

Black Cole Haan American Classics Pinch Penny Loafer

Black Cole Haan American Classics Pinch Penny Loafer

+2

Brand Name: Cole Haan
Product Name: American Classics Pinch Penny Loafer
Gender: Men's
Color: Truffle/Natural
Price: $205.20MSRP: $228.0010% OFF
Rating: 4Rated 4 stars out of 5(30)

Join Our List, Get 10% Off

Sign up for Zappos emails—new subscribers get 10% off a future order!* Plus, get early access to sales, coupons, and more. (One code per email address.)