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

Size 8.5 Penny Keeper Black Shoes

45 items found

Sort By

Your Selections

Search Results

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
Gender: Men's
Color: Black II
Price: $79.95MSRP: $115.00
Rating: 4Rated 4 stars out of 5(397)

Cole Haan - American Classics Penny Loafer. Color Black/Black. $158.00. 4.2 out of 5 stars

Black Cole Haan American Classics Penny Loafer

Black Cole Haan American Classics Penny Loafer

+2

Brand Name: Cole Haan
Product Name: American Classics Penny Loafer
Gender: Men's
Color: Black/Black
Price: $158.00
Rating: 4Rated 4 stars out of 5(356)

ECCO - S Lite Moc Penny Loafer. Color Black. $170.00. 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: $170.00
Rating: 4Rated 4 stars out of 5(4)

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

Black Florsheim Throttle Penny

Black Florsheim Throttle Penny

+4

Brand Name: Florsheim
Product Name: Throttle Penny
Gender: Men's
Color: Black II
Price: $79.95MSRP: $110.00
Rating: 4Rated 4 stars out of 5(13)

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(90)

Johnston & Murphy - Hayes Penny Loafer. Color Black. On sale for $99.90. MSRP $135.00.. 4.1 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: $135.00
Rating: 4Rated 4 stars out of 5(60)

Cole Haan - Wyatt Penny Driver. Color Black/Black. $125.00. 4.3 out of 5 stars

Black Cole Haan Wyatt Penny Driver

Black Cole Haan Wyatt Penny Driver

+5

Brand Name: Cole Haan
Product Name: Wyatt Penny Driver
Gender: Men's
Color: Black/Black
Price: $125.00
Rating: 4Rated 4 stars out of 5(281)

Cole Haan - Grand Laser Penny Driver. Color Black/Black. On sale for $105.00. MSRP $168.00.. 3.9 out of 5 stars

Black Cole Haan Grand Laser Penny Driver

Black Cole Haan Grand Laser Penny Driver

+4

Brand Name: Cole Haan
Product Name: Grand Laser Penny Driver
Gender: Men's
Color: Black/Black
Price: $105.00MSRP: $168.00
Rating: 4Rated 4 stars out of 5(69)

Cole Haan - Pinch Weekender Penny Textured. Color Dark Chocolate Pebble/Ivory. On sale for $80.00. 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
Gender: Men's
Color: Dark Chocolate Pebble/Ivory
Price: $80.00MSRP: $100.00
Rating: 4Rated 4 stars out of 5(2)

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(295)

Florsheim - Berkley Flex Penny Loafer. Color Black Smooth. $124.95. 4.3 out of 5 stars

Black Florsheim Berkley Flex Penny Loafer

Black Florsheim Berkley Flex Penny Loafer

+5

Brand Name: Florsheim
Product Name: Berkley Flex Penny Loafer
Gender: Men's
Color: Black Smooth
Price: $124.95
Rating: 4Rated 4 stars out of 5(151)

Florsheim - Sorrento Moc Toe Penny Loafer. Color Black Smooth. $129.95. 4.2 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(41)

Cole Haan - Pinch Prep Penny Loafer. Color Black Brushoff. On sale for $119.99. MSRP $227.95.. 4.0 out of 5 stars

Black Cole Haan Pinch Prep Penny Loafer

Black Cole Haan Pinch Prep Penny Loafer

+5

Brand Name: Cole Haan
Product Name: Pinch Prep Penny Loafer
Gender: Men's
Color: Black Brushoff
Price: $119.99MSRP: $227.95
Rating: 4Rated 4 stars out of 5(7)

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
Gender: Men's
Color: Black
Price: $99.97MSRP: $110.00
Rating: 3Rated 3 stars out of 5(3)

Marc Joseph New York - Nebraska. Color Black Grainy. On sale for $79.95. MSRP $185.00.. 4.5 out of 5 stars

Black Marc Joseph New York Nebraska

Black Marc Joseph New York Nebraska

+10

Brand Name: Marc Joseph New York
Product Name: Nebraska
Gender: Men's
Color: Black Grainy
Price: $79.95MSRP: $185.00
Rating: 5Rated 5 stars out of 5(6)

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

+2

Brand Name: Massimo Matteo
Product Name: Florencia Penny Driver
Gender: Men's
Color: Black
Price: $53.10MSRP: $59.00
Rating: 4Rated 4 stars out of 5(51)

Born - Simon III. Color Black Full Grain. On sale for $103.20. MSRP $120.00.. 4.5 out of 5 stars

Black Born Simon III

Black Born Simon III

+2

Brand Name: Born
Product Name: Simon III
Gender: Men's
Color: Black Full Grain
Price: $103.20MSRP: $120.00
Rating: 5Rated 5 stars out of 5(2)

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

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)

Johnston & Murphy - Lyles Penny. Color Black Full Grain. On sale for $119.99. MSRP $165.00..

Black Johnston & Murphy Lyles Penny

Black Johnston & Murphy Lyles Penny

+2

Brand Name: Johnston & Murphy
Product Name: Lyles Penny
Gender: Men's
Color: Black Full Grain
Price: $119.99MSRP: $165.00
Rating

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

Nunn Bush - Drexel Moc Toe Penny Loafer with KORE Walking Comfort Technology. Color Black. On sale for $69.99. MSRP $100.00.. 4.4 out of 5 stars

Black Nunn Bush Drexel Moc Toe Penny Loafer with KORE Walking Comfort Technology

Black 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: Black
Price: $69.99MSRP: $100.00
Rating: 4Rated 4 stars out of 5(155)

Cole Haan - American Classics Pinch Penny Loafer. Color Truffle/Natural. $228.00. 4.0 out of 5 stars

Black Cole Haan American Classics Pinch Penny Loafer

Black Cole Haan American Classics Pinch Penny Loafer

+5

Brand Name: Cole Haan
Product Name: American Classics Pinch Penny Loafer
Gender: Men's
Color: Truffle/Natural
Price: $228.00
Rating: 4Rated 4 stars out of 5(28)

Johnston & Murphy Collection - Baldwin Driver Penny. Color Black. $185.00. 3.7 out of 5 stars

Black Johnston & Murphy Collection Baldwin Driver Penny

Black Johnston & Murphy Collection Baldwin Driver Penny

+3

Brand Name: Johnston & Murphy Collection
Product Name: Baldwin Driver Penny
Gender: Men's
Color: Black
Price: $185.00
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
Gender: Men's
Color: Black
Price: $189.95
Rating: 5Rated 5 stars out of 5(1)

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

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: $185.00
Rating

Marc Joseph New York - Union Street 2. Color Black Grainy. $155.00. 4.8 out of 5 stars

Black Marc Joseph New York Union Street 2

Black Marc Joseph New York Union Street 2

+3

Brand Name: Marc Joseph New York
Product Name: Union Street 2
Gender: Men's
Color: Black Grainy
Price: $155.00
Rating: 5Rated 5 stars out of 5(4)

Tommy Hilfiger - Amile. Color Black. $59.95. 4.5 out of 5 stars

Black Tommy Hilfiger Amile

Black Tommy Hilfiger Amile

+4

Brand Name: Tommy Hilfiger
Product Name: Amile
Gender: Men's
Color: Black
Price: $59.95
Rating: 5Rated 5 stars out of 5(4)

Nunn Bush - Noah Beef Roll Penny Loafer. Color Black. On sale for $69.95. MSRP $100.00.. 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: $69.95MSRP: $100.00
Rating: 4Rated 4 stars out of 5(63)

Nunn Bush - Centro Flex Moccasin Toe Penny Loafer Slip-On. Color Black. $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
Gender: Men's
Color: Black
Price: $100.00
Rating: 5Rated 5 stars out of 5(7)

Frye - Tyler Penny. Color Black 1. $257.95.

Black Frye Tyler Penny

Black Frye Tyler Penny

+4

Brand Name: Frye
Product Name: Tyler Penny
Gender: Men's
Color: Black 1
Price: $257.95
Rating

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

+3

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)

Johnston & Murphy Collection - Baldwin Penny. Color Black. $195.00. 4.7 out of 5 stars

Black Johnston & Murphy Collection Baldwin Penny

Black Johnston & Murphy Collection Baldwin Penny

+5

Brand Name: Johnston & Murphy Collection
Product Name: Baldwin Penny
Gender: Men's
Color: Black
Price: $195.00
Rating: 5Rated 5 stars out of 5(26)

Magnanni - Lawford. Color Black. $445.00.

Black Magnanni Lawford

Black Magnanni Lawford

+2

Brand Name: Magnanni
Product Name: Lawford
Gender: Men's
Color: Black
Price: $445.00
Rating

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

2 left in stock

Black Johnston & Murphy Cort Penny

Black Johnston & Murphy Cort Penny

+2

Brand Name: Johnston & Murphy
Product Name: Cort Penny
Gender: Men's
Color: Black Full Grain Leather
Price: $145.00
Rating: 5Rated 5 stars out of 5(76)

Born - Taylor. Color Black Full Grain Leather. Low Stock. On sale for $111.60. MSRP $120.00.. 4.0 out of 5 stars

1 left in stock

Black Born Taylor

Black Born Taylor

Brand Name: Born
Product Name: Taylor
Gender: Men's
Color: Black Full Grain Leather
Price: $111.60MSRP: $120.00
Rating: 4Rated 4 stars out of 5(5)

Polo Ralph Lauren - Anders Penny. Color Black. $168.00. 4.0 out of 5 stars

Black Polo Ralph Lauren Anders Penny

Black Polo Ralph Lauren Anders Penny

+2

Brand Name: Polo Ralph Lauren
Product Name: Anders Penny
Gender: Men's
Color: Black
Price: $168.00
Rating: 4Rated 4 stars out of 5(1)

Marc Joseph New York - Washington. Color Black Napa. Low Stock. On sale for $154.05. MSRP $195.00.. 4.4 out of 5 stars

9 left in stock

Black Marc Joseph New York Washington

Black Marc Joseph New York Washington

+4

Brand Name: Marc Joseph New York
Product Name: Washington
Gender: Men's
Color: Black Napa
Price: $154.05MSRP: $195.00
Rating: 4Rated 4 stars out of 5(5)

Steve Madden - Crescent. Color Black Velvet. $99.99.

Black Steve Madden Crescent

Black Steve Madden Crescent

Brand Name: Steve Madden
Product Name: Crescent
Gender: Men's
Color: Black Velvet
Price: $99.99
Rating

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)

Bruno Magli - Manfredo. Color Black. Low Stock. On sale for $276.50. MSRP $395.00.. 4.7 out of 5 stars

4 left in stock

Black Bruno Magli Manfredo

Black Bruno Magli Manfredo

+1

Brand Name: Bruno Magli
Product Name: Manfredo
Gender: Men's
Color: Black
Price: $276.50MSRP: $395.00
Rating: 5Rated 5 stars out of 5(3)

Marc Joseph New York - East Village Mens. Color Black Napa. Low Stock. $175.00.

7 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
Gender: Men's
Color: Black Napa
Price: $175.00
Rating

Anthony Veer - Gerry Penny Loafer. Color Black. Low Stock. $199.95. 2.0 out of 5 stars

6 left in stock

Black Anthony Veer Gerry Penny Loafer

Black Anthony Veer Gerry Penny Loafer

+2

Brand Name: Anthony Veer
Product Name: Gerry Penny Loafer
Gender: Men's
Color: Black
Price: $199.95
Rating: 2Rated 2 stars out of 5(1)

Bruno Magli - Tonio. Color Black Cervo. $395.00. 5.0 out of 5 stars

Black Bruno Magli Tonio

Black Bruno Magli Tonio

Brand Name: Bruno Magli
Product Name: Tonio
Gender: Men's
Color: Black Cervo
Price: $395.00
Rating: 5Rated 5 stars out of 5(1)

Sebago - Byron. Color Black. Low Stock. On sale for $127.75. MSRP $165.00.. 2.0 out of 5 stars

8 left in stock

Black Sebago Byron

Black Sebago Byron

Brand Name: Sebago
Product Name: Byron
Gender: Men's
Color: Black
Price: $127.75MSRP: $165.00
Rating: 2Rated 2 stars out of 5(1)

Get on the List

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