EXTRA 20% OFF*
*Offer ends 12/29/25 at 11:59pm PST. Exclusions apply.
Hurry, hurry: use code SAVE20
Select styles only.
Shop Now

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

Size 9 Medium Size Penny Keeper Products

34 items found

Sort By

Your Selections

Search Results

Florsheim - Throttle Penny. Color Brown Crazy Horse II. On sale for $79.95. MSRP $110.00. 27% off. 4.0 out of 5 stars

Brown Florsheim Throttle Penny

Brown Florsheim Throttle Penny

+2

Brand Name: Florsheim
Product Name: Throttle Penny
Gender: Men's
Color: Brown Crazy Horse II
Price: $79.95MSRP: $11027% OFF
Rating: 4Rated 4 stars out of 5(21)

Rockport - Classic Loafer Lite Penny. Color Cognac. On sale for $89.95. MSRP $124.95. 28% off. 3.9 out of 5 stars

Tan Rockport Classic Loafer Lite Penny

Tan Rockport Classic Loafer Lite Penny

+3

Brand Name: Rockport
Product Name: Classic Loafer Lite Penny
Gender: Men's
Color: Cognac
Price: $89.95MSRP: $124.9528% OFF
Rating: 4Rated 4 stars out of 5(414)

Johnston & Murphy - Dayton Penny Loafer. Color Brown. On sale for $147.00. MSRP $245.00. 40% off. 5.0 out of 5 stars

Brown Johnston & Murphy Dayton Penny Loafer

Brown Johnston & Murphy Dayton Penny Loafer

Brand Name: Johnston & Murphy
Product Name: Dayton Penny Loafer
Gender: Men's
Color: Brown
Price: $147MSRP: $24540% OFF
Rating: 5Rated 5 stars out of 5(7)

Dockers - Colleague. Color Cordovan. On sale for $49.99. MSRP $90.00. 44% off. 4.0 out of 5 stars

Burgundy Dockers Colleague

Burgundy Dockers Colleague

+3

Brand Name: Dockers
Product Name: Colleague
Gender: Men's
Color: Cordovan
Price: $49.99MSRP: $9044% OFF
Rating: 4Rated 4 stars out of 5(5)

Marc Joseph New York - Monaco. Color Tan Napa. On sale for $59.45. MSRP $185.00. 68% off. 3.5 out of 5 stars

Tan Marc Joseph New York Monaco

Tan Marc Joseph New York Monaco

+5

Brand Name: Marc Joseph New York
Product Name: Monaco
Gender: Men's
Color: Tan Napa
Price: $59.45MSRP: $18568% OFF
Rating: 4Rated 4 stars out of 5(4)

Marc Joseph New York - Nebraska. Color Grey Suede. On sale for $79.95. MSRP $185.00. 57% off. 3.9 out of 5 stars

Gray Marc Joseph New York Nebraska

Gray Marc Joseph New York Nebraska

+7

Brand Name: Marc Joseph New York
Product Name: Nebraska
Gender: Men's
Color: Grey Suede
Price: $79.95MSRP: $18557% OFF
Rating: 4Rated 4 stars out of 5(17)

Florsheim - Sorrento Moc Toe Penny Loafers. Color Cognac Smooth. On sale for $109.95. MSRP $145.00. 24% off. 4.3 out of 5 stars

Neutral Florsheim Sorrento Moc Toe Penny Loafers

Neutral Florsheim Sorrento Moc Toe Penny Loafers

+2

Brand Name: Florsheim
Product Name: Sorrento Moc Toe Penny Loafers
Gender: Men's
Color: Cognac Smooth
Price: $109.95MSRP: $14524% OFF
Rating: 4Rated 4 stars out of 5(54)

Nunn Bush - Odin II Moc Toe Penny Loafer Lightweight and Comfortable Slip-On. Color Burgundy. On sale for $79.95. MSRP $110.00. 27% off. 5.0 out of 5 stars

Burgundy Nunn Bush Odin II Moc Toe Penny Loafer Lightweight and Comfortable Slip-On

Burgundy Nunn Bush Odin II Moc Toe Penny Loafer Lightweight and Comfortable Slip-On

+3

Brand Name: Nunn Bush
Product Name: Odin II Moc Toe Penny Loafer Lightweight and Comfortable Slip-On
Gender: Men's
Color: Burgundy
Price: $79.95MSRP: $11027% OFF
Rating: 5Rated 5 stars out of 5(3)

Tommy Hilfiger - Ruven. Color Black. On sale for $69.35. MSRP $95.00. 27% off.

Black Tommy Hilfiger Ruven

Black Tommy Hilfiger Ruven

+2

Brand Name: Tommy Hilfiger
Product Name: Ruven
Gender: Men's
Color: Black
Price: $69.35MSRP: $9527% OFF
Rating

Johnston & Murphy - Hayes Penny Loafers. Color Burgundy. $119.90. 4.1 out of 5 stars

Burgundy Johnston & Murphy Hayes Penny Loafers

Burgundy Johnston & Murphy Hayes Penny Loafers

+2

Brand Name: Johnston & Murphy
Product Name: Hayes Penny Loafers
Gender: Men's
Color: Burgundy
Price: $119.90
Rating: 4Rated 4 stars out of 5(117)

Nunn Bush - Drexel Moc Toe Penny Loafer with KORE Walking Comfort Technology. Color Black. On sale for $69.99. MSRP $110.00. 36% off. 4.3 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: $11036% OFF
Rating: 4Rated 4 stars out of 5(174)

Steve Madden - Belleaire. Color Tan. On sale for $70.00. MSRP $140.00. 50% off.

Tan Steve Madden Belleaire

Tan Steve Madden Belleaire

+2

Brand Name: Steve Madden
Product Name: Belleaire
Gender: Men's
Color: Tan
Price: $70MSRP: $14050% OFF
Rating

Nunn Bush - Lincoln Penny Loafer. Color Black Polished. On sale for $69.95. MSRP $100.00. 30% off. 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: $69.95MSRP: $10030% OFF
Rating: 4Rated 4 stars out of 5(323)

Nunn Bush - Noah Beef Roll Penny Loafers. Color Black. On sale for $65.39. MSRP $110.00. 41% off. 4.1 out of 5 stars

Black Nunn Bush Noah Beef Roll Penny Loafers

Black Nunn Bush Noah Beef Roll Penny Loafers

+2

Brand Name: Nunn Bush
Product Name: Noah Beef Roll Penny Loafers
Gender: Men's
Color: Black
Price: $65.39MSRP: $11041% OFF
Rating: 4Rated 4 stars out of 5(67)

Samuel Hubbard - Free Spirit for Him. Color Black Tumbled Leather. $195.00. 3.5 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
Rating: 4Rated 4 stars out of 5(4)

Rockport - Liam. Color Dark Brown Leather. On sale for $64.97. MSRP $129.95. 50% off. 4.3 out of 5 stars

Brown Rockport Liam

Brown Rockport Liam

Brand Name: Rockport
Product Name: Liam
Gender: Men's
Color: Dark Brown Leather
Price: $64.97MSRP: $129.9550% OFF
Rating: 4Rated 4 stars out of 5(3)

Steve Madden - Santee. Color Black 1. On sale for $109.89. MSRP $120.00. 8% off.

Black Steve Madden Santee

Black Steve Madden Santee

Brand Name: Steve Madden
Product Name: Santee
Gender: Men's
Color: Black 1
Price: $109.89MSRP: $1208% OFF
Rating

Marc Joseph New York - Union Street 2. Color Olive Suede. Low Stock. On sale for $124.00. MSRP $155.00. 20% off. 4.8 out of 5 stars

Low Stock

Olive Marc Joseph New York Union Street 2

Olive Marc Joseph New York Union Street 2

+3

Brand Name: Marc Joseph New York
Product Name: Union Street 2
Gender: Men's
Color: Olive Suede
Price: $124MSRP: $15520% OFF
Rating: 5Rated 5 stars out of 5(4)

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

Brown Marc Joseph New York River Road

Brown Marc Joseph New York River Road

+3

Brand Name: Marc Joseph New York
Product Name: River Road
Gender: Men's
Color: Cognac Grainy
Price: $69.95MSRP: $18562% OFF
Rating: 5Rated 5 stars out of 5(1)

Steve Madden - Crescent. Color Black Velvet. On sale for $69.97. MSRP $100.00. 30% off. 5.0 out of 5 stars

Black Steve Madden Crescent

Black Steve Madden Crescent

Brand Name: Steve Madden
Product Name: Crescent
Gender: Men's
Color: Black Velvet
Price: $69.97MSRP: $10030% OFF
Rating: 5Rated 5 stars out of 5(1)

Tommy Hilfiger - Tabaro. Color Cognac. Low Stock. On sale for $49.50. MSRP $99.00. 50% off.

Low Stock

Tan Tommy Hilfiger Tabaro

Tan Tommy Hilfiger Tabaro

Brand Name: Tommy Hilfiger
Product Name: Tabaro
Gender: Men's
Color: Cognac
Price: $49.50MSRP: $9950% OFF
Rating

Tommy Hilfiger - Amile. Color Dark Brown. On sale for $59.63. MSRP $89.00. 33% off. 4.6 out of 5 stars

Brown Tommy Hilfiger Amile

Brown Tommy Hilfiger Amile

+4

Brand Name: Tommy Hilfiger
Product Name: Amile
Gender: Men's
Color: Dark Brown
Price: $59.63MSRP: $8933% OFF
Rating: 5Rated 5 stars out of 5(5)

Johnston & Murphy - Baldwin Penny. Color Navy Waxed English Suede/Brown Full Grain. On sale for $149.99. MSRP $218.00. 31% off. 4.4 out of 5 stars

Brown Johnston & Murphy Baldwin Penny

Brown Johnston & Murphy Baldwin Penny

+7

Brand Name: Johnston & Murphy
Product Name: Baldwin Penny
Gender: Men's
Color: Navy Waxed English Suede/Brown Full Grain
Price: $149.99MSRP: $21831% OFF
Rating: 4Rated 4 stars out of 5(52)

Florsheim - Berkley Flex Penny Loafers. Color Burgundy. On sale for $116.54. MSRP $140.00. 17% off. 4.2 out of 5 stars

Burgundy Florsheim Berkley Flex Penny Loafers

Burgundy Florsheim Berkley Flex Penny Loafers

+5

Brand Name: Florsheim
Product Name: Berkley Flex Penny Loafers
Gender: Men's
Color: Burgundy
Price: $116.54MSRP: $14017% OFF
Rating: 4Rated 4 stars out of 5(227)

Polo Ralph Lauren - Anders Penny. Color Black. $168.00. 3.0 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
Rating: 3Rated 3 stars out of 5(2)

Frye - Tyler Flex Penny. Color Mushroom. Low Stock. On sale for $99.00. MSRP $198.00. 50% off. 4.1 out of 5 stars

Low Stock

Neutral Frye Tyler Flex Penny

Neutral Frye Tyler Flex Penny

+5

Brand Name: Frye
Product Name: Tyler Flex Penny
Gender: Men's
Color: Mushroom
Price: $99MSRP: $19850% OFF
Rating: 4Rated 4 stars out of 5(8)

Cole Haan - Grand Laser Penny Driver. Color Black/Black. On sale for $69.97. MSRP $150.00. 53% off. 4.0 out of 5 stars

Black Cole Haan Grand Laser Penny Driver

Black Cole Haan Grand Laser Penny Driver

+2

Brand Name: Cole Haan
Product Name: Grand Laser Penny Driver
Gender: Men's
Color: Black/Black
Price: $69.97MSRP: $15053% OFF
Rating: 4Rated 4 stars out of 5(74)

Cole Haan - Pinch Prep Penny Loafer. Color Birchbeige Suede/Dark Chocolate. On sale for $114.74. MSRP $130.00. 12% off. 4.0 out of 5 stars

Beige Cole Haan Pinch Prep Penny Loafer

Beige Cole Haan Pinch Prep Penny Loafer

+4

Brand Name: Cole Haan
Product Name: Pinch Prep Penny Loafer
Gender: Men's
Color: Birchbeige Suede/Dark Chocolate
Price: $114.74MSRP: $13012% OFF
Rating: 4Rated 4 stars out of 5(11)

Polo Ralph Lauren - Alston Penny. Color Tan. $178.00. 4.0 out of 5 stars

Tan Polo Ralph Lauren Alston Penny

Tan Polo Ralph Lauren Alston Penny

+2

Brand Name: Polo Ralph Lauren
Product Name: Alston Penny
Gender: Men's
Color: Tan
Price: $178
Rating: 4Rated 4 stars out of 5(2)

Stacy Adams - Spencer Penny Slip-On. Color Tan. On sale for $65.00. MSRP $130.00. 50% off. 4.8 out of 5 stars

Tan Stacy Adams Spencer Penny Slip-On

Tan Stacy Adams Spencer Penny Slip-On

+2

Brand Name: Stacy Adams
Product Name: Spencer Penny Slip-On
Gender: Men's
Color: Tan
Price: $65MSRP: $13050% OFF
Rating: 5Rated 5 stars out of 5(9)

Florsheim - Zaffiro Moc Toe Penny Loafers. Color Black. $144.99. 4.7 out of 5 stars

Black Florsheim Zaffiro Moc Toe Penny Loafers

Black Florsheim Zaffiro Moc Toe Penny Loafers

+2

Brand Name: Florsheim
Product Name: Zaffiro Moc Toe Penny Loafers
Gender: Men's
Color: Black
Price: $144.99
Rating: 5Rated 5 stars out of 5(17)

Cole Haan - Wyatt Penny Driver. Color Black/Black. On sale for $111.14. MSRP $140.00. 21% off. 4.3 out of 5 stars

Black Cole Haan Wyatt Penny Driver

Black Cole Haan Wyatt Penny Driver

+2

Brand Name: Cole Haan
Product Name: Wyatt Penny Driver
Gender: Men's
Color: Black/Black
Price: $111.14MSRP: $14021% OFF
Rating: 4Rated 4 stars out of 5(283)

ECCO - S Lite Moc Penny Loafers. Color Cognac. On sale for $174.95. MSRP $179.95. 3% off. 4.0 out of 5 stars

Tan ECCO S Lite Moc Penny Loafers

Tan ECCO S Lite Moc Penny Loafers

+2

Brand Name: ECCO
Product Name: S Lite Moc Penny Loafers
Gender: Men's
Color: Cognac
Price: $174.95MSRP: $179.953% OFF
Rating: 4Rated 4 stars out of 5(4)

PIKOLINOS - Avila M1T-3205. Color Black. Low Stock. $195.00. 5.0 out of 5 stars

Low Stock

Black PIKOLINOS Avila M1T-3205

Black PIKOLINOS Avila M1T-3205

Brand Name: PIKOLINOS
Product Name: Avila M1T-3205
Gender: Men's
Color: Black
Price: $195
Rating: 5Rated 5 stars out of 5(1)

Join Our Email List

Never miss out on latest drops & sales—plus, new subscribers get 10% off.*

*One code per email address.