Skip to main content

Enjoy Holiday Savings on New In-Season Markdowns up to 33% - 40% off select styles - SHOP NOW

iPhone Updates & Can't Find Our Emails in Your Inbox? - CLICK HERE

The 2025 Dillard's Christmas Gift Guide is here - Volume 3 - SHOP NOW

Check For In-Store Availability On The Products You Love - LEARN MORE

EARN POINTS WHEN YOU USE YOUR DILLARD’S CREDIT CARD - LEARN MORE

  • Dillard's Logo
  • Back In Stock
  • Sale and Clearance
  • Shop By Brand
  • Limited Availability
  • Credit Card
  • Store LocatorFind a Store
Shop Dillards.com - The Style of Christmas
When typing in this field, a list of search results will appear and be automatically updated as you type.
User Login IconLogin
  • Login
  • My Dillard's Account
  • Just For You
  • Order History
  • Returns
  • My Wish List
  • Find a Store
Shopping Bag(0) items in cart
  • Women
  • Juniors
  • Men
  • Kids
  • Shoes
  • Handbags
  • Accessories
  • Lingerie
  • Home
  • Beauty
  • Dillard's Exclusive
  • Just For You
  • Shoes
  • Men's Shoes

Men's Penny Keeper Shoes

Just For You
  • Just For You
    (Edit)
New Arrivals
  • New Arrivals
Sale
  • Sale

Category

  • Dress Shoes
  • Casual Shoes
  • Comfort

Brand

search
Brand
  • ALDO
  • ALIGN
  • Birkenstock
  • Born
  • Bruno Magli
  • COACH
  • Cole Haan
  • ECCO
  • Flag LTD.
  • Frye
  • G.H. Bass
  • Hugo Boss
  • Johnnie-O
  • Johnston & Murphy
  • Josef Seibel
  • Kurt Geiger London
  • Magnanni
  • Marc Nolan
  • Polo Ralph Lauren
  • Sperry
  • Steve Madden
  • Taft
  • Ted Baker London
  • To Boot New York
  • Vionic
color
  • Black
  • Grey
  • White
  • Ivory
  • Tan
  • Brown
  • Red
  • Pink
  • Orange
  • Yellow
  • Green
  • Blue
  • Animal
  • Floral
size
  • 6
  • 7
  • 7.5
  • 8
  • 8.5
  • 9
  • 9.5
  • 10
  • 10.5
  • 11
  • 11.5
  • 12
  • 12.5
  • 13
  • 14
  • 15
  • 16
shoe width
  • Medium
  • Wide
occasion
  • Career
  • Casual
  • Daytime Occasion
  • Social/Cocktail/Evening
styling feature
  • Penny Keeper
  • Studs
shoe silhouette
  • Clog
  • Driver
  • Huarache
  • Loafer
  • Mule
  • Venetian
platform height
  • Flat
  • Low
  • All
  • Dress Shoes
  • Casual Shoes
  • Comfort
clear allPenny Keeperclear filter
  • 123 Items
  • 1
  • 2
  • Next Page
  • Last
Polo Ralph Lauren Men's Anders Leather Penny LoafersMen's Anders Leather Penny Loafers

Polo Ralph LaurenMen's Anders Leather Penny Loafers

Extended Sizes
Rated 4.0526 out of 5 starsRated 4.0526 out of 5 starsRated 4.0526 out of 5 starsRated 4.0526 out of 5 starsRated 4.0526 out of 5 stars(19)
Flag LTD. Men's Mario Leather Driver Penny LoafersMen's Mario Leather Driver Penny Loafers

Flag LTD.Men's Mario Leather Driver Penny Loafers

Save on Select Items
Orig.
Now
Dillard's Exclusive
Rated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 stars(12)
Johnston & Murphy Men's Harrison Leather Penny LoafersMen's Harrison Leather Penny Loafers

Johnston & MurphyMen's Harrison Leather Penny Loafers

Birkenstock Men's Naples Wrapped Leather Penny Keeper ClogsMen's Naples Wrapped Leather Penny Keeper Clogs

BirkenstockMen's Naples Wrapped Leather Penny Keeper Clogs

Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)
Marc Nolan Men's Calum Badlands Croco Embossed Leather Penny LoafersMen's Calum Badlands Croco Embossed Leather Penny Loafers

Marc NolanMen's Calum Badlands Croco Embossed Leather Penny Loafers

Extended Sizes
Marc Nolan Men's Calum Cow Print Fur Penny LoafersMen's Calum Cow Print Fur Penny Loafers

Marc NolanMen's Calum Cow Print Fur Penny Loafers

Extended Sizes
Steve Madden Men's Boca Leather Penny LoafersMen's Boca Leather Penny Loafers

Steve MaddenMen's Boca Leather Penny Loafers

Extended Sizes
Birkenstock Men's Naples Suede Wrapped Penny Keeper ClogsMen's Naples Suede Wrapped Penny Keeper Clogs

BirkenstockMen's Naples Suede Wrapped Penny Keeper Clogs

Rated 3.5 out of 5 starsRated 3.5 out of 5 starsRated 3.5 out of 5 starsRated 3.5 out of 5 starsRated 3.5 out of 5 stars(2)
Men's Anders Leather Penny Loafers

PLACEHOLDERMen's Anders Leather Penny Loafers

Extended Sizes
Rated 4.0526 out of 5 starsRated 4.0526 out of 5 starsRated 4.0526 out of 5 starsRated 4.0526 out of 5 starsRated 4.0526 out of 5 stars(19)

Johnston & MurphyMen's Emmett Leather Penny Loafers

Rated 4.4133 out of 5 starsRated 4.4133 out of 5 starsRated 4.4133 out of 5 starsRated 4.4133 out of 5 starsRated 4.4133 out of 5 stars(75)

Cole HaanMen's Pinch Penny Loafers

Extended Sizes
Rated 4.2727 out of 5 starsRated 4.2727 out of 5 starsRated 4.2727 out of 5 starsRated 4.2727 out of 5 starsRated 4.2727 out of 5 stars(55)

PLACEHOLDERMen's Anders Leather Penny Loafers

Extended Sizes
Rated 4.0526 out of 5 starsRated 4.0526 out of 5 starsRated 4.0526 out of 5 starsRated 4.0526 out of 5 starsRated 4.0526 out of 5 stars(19)

Johnston & MurphyMen's Collier Suede Penny Loafers

Extended Sizes
Rated 4.8 out of 5 starsRated 4.8 out of 5 starsRated 4.8 out of 5 starsRated 4.8 out of 5 starsRated 4.8 out of 5 stars(5)

Marc NolanMen's Adler Mixed Leather Lug Penny Loafers

Extended Sizes

PLACEHOLDERMen's Anders Leather Penny Loafers

Extended Sizes
Rated 4.0526 out of 5 starsRated 4.0526 out of 5 starsRated 4.0526 out of 5 starsRated 4.0526 out of 5 starsRated 4.0526 out of 5 stars(19)

Flag LTD.Mario Woven Leather Penny Driver Loafers

Dillard's Exclusive
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Cole HaanMen's Wyatt Leather Penny Driver Loafers

Extended Sizes
Rated 2.3333 out of 5 starsRated 2.3333 out of 5 starsRated 2.3333 out of 5 starsRated 2.3333 out of 5 starsRated 2.3333 out of 5 stars(3)

PLACEHOLDERMen's Anders Leather Penny Loafers

Extended Sizes
Rated 4.0526 out of 5 starsRated 4.0526 out of 5 starsRated 4.0526 out of 5 starsRated 4.0526 out of 5 starsRated 4.0526 out of 5 stars(19)

Johnston & MurphyMens Gibbons Embossed Leather Penny Loafers

Extended Sizes

Marc NolanMen's Adler Glazed Leather Penny Loafers

Extended Sizes

Flag LTD.Men's Vincent Leather Penny Loafers

Dillard's Exclusive
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(9)

Cole HaanMen's Ledley Grand Leather Penny Loafers

Save on Select Items
Orig.
Now
Rated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 stars(1)

Steve MaddenMen's Santee Velvet Dress Penny Loafers

Johnston & MurphyCollection Men's Baldwin Suede Penny Loafers

Internet Exclusive

Johnston & MurphyHayes Oiled Leather Penny Keeper Loafers

Rated 4.3655 out of 5 starsRated 4.3655 out of 5 starsRated 4.3655 out of 5 starsRated 4.3655 out of 5 starsRated 4.3655 out of 5 stars(145)

Marc NolanMen's Del Mar Croco Embossed Suede Penny Loafer Mules

Internet Exclusive
Extended Sizes

Johnston & MurphyMen's XC+Copley Waterproof Penny Loafer

Internet Exclusive
Extended Sizes
Rated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 stars(2)

Marc NolanMen's Calum Pebble Leather and Mesh Penny Loafers

Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Marc NolanMen's Del Mar Cow Print Dark Horse Penny Loafer Mules

Internet Exclusive
Extended Sizes

Flag LTD.Men's Mario Crocodile Embossed Leather Penny Loafer Drivers

Dillard's Exclusive

Marc NolanMen's Adler Colorblock Croco Embossed Leather Penny Loafers

Internet Exclusive
Extended Sizes

COACHMen's Signature Coin Leather Driver Loafers

ECCOMen's Metropole Verona Leather Penny Loafers

Internet Exclusive

Johnston & MurphyMen's Collier Leather Penny Loafers

Extended Sizes
Rated 3.8571 out of 5 starsRated 3.8571 out of 5 starsRated 3.8571 out of 5 starsRated 3.8571 out of 5 starsRated 3.8571 out of 5 stars(7)

Marc NolanMen's Calum Croco Embossed Leather Penny Loafers

Extended Sizes

Marc NolanMen's Abe Patent Leather and Suede Penny Loafers

Extended Sizes

BornMen's Marcel Leather Penny Driver Loafers

Rated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 stars(1)

ECCOMen's Lite Leather Moc Penny Loafers

Extended Sizes
Rated 4.2 out of 5 starsRated 4.2 out of 5 starsRated 4.2 out of 5 starsRated 4.2 out of 5 starsRated 4.2 out of 5 stars(5)

Steve MaddenMen's Ashland Leather Penny Loafers

Extended Sizes

Johnston & MurphyCollection Mens Baldwin Suede Penny Loafers

Rated 3.5 out of 5 starsRated 3.5 out of 5 starsRated 3.5 out of 5 starsRated 3.5 out of 5 starsRated 3.5 out of 5 stars(2)

Steve MaddenMen's Natan Leather Contrast Stitch Penny Loafers

Extended Sizes
Rated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 starsRated 4.25 out of 5 stars(4)

Josef SeibelMen's Stuart 08 Leather Penny Loafers

Cole HaanMen's Davies Grand Penny Driver Loafers

ALIGNMen's Archer Penny Loafers

Johnston & MurphyCollection Men's Baldwin Leather Penny Loafers

Rated 4.1034 out of 5 starsRated 4.1034 out of 5 starsRated 4.1034 out of 5 starsRated 4.1034 out of 5 starsRated 4.1034 out of 5 stars(29)

Marc NolanMen's Clint Suede Kiltie Loafers

Internet Exclusive
Extended Sizes

SperryMen's Authentic Original Harbor Penny Loafers

G.H. BassMen's 1936 Logan Weejun Leather Penny Loafers

Internet Exclusive
Extended Sizes
Only size 7.5, 10 available
Rated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 stars(1)

Marc NolanMen's Calum Patent Leather and Mesh Penny Loafers

Internet Exclusive
Extended Sizes

Steve MaddenMen's Zephyr Leather Lug Penny Loafers

Extended Sizes

Marc NolanMen's Adler Patent Leather Penny Loafers

Extended Sizes

Cole HaanMen's Carnegie Penny Loafers

Marc NolanMen's Adler Patent Tortoise Print Penny Loafers

Internet Exclusive
Extended Sizes

COACHMen's Reagan Patent Leather Penny Loafers

Internet Exclusive
Rated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 stars(4)

MagnanniMen's Shayne Leather Woven Penny Loafers

Polo Ralph LaurenMen's Alston Penny Loafers

Internet Exclusive
Extended Sizes
Rated 4.8889 out of 5 starsRated 4.8889 out of 5 starsRated 4.8889 out of 5 starsRated 4.8889 out of 5 starsRated 4.8889 out of 5 stars(9)

Johnston & MurphyMen's Beck Leather Slip On Penny Loafers

Rated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 stars(1)

Marc NolanMen's Adler Pebble Leather Lug Penny Loafers

Internet Exclusive
Extended Sizes

Cole HaanMen's Grand Leather Laser Cut Penny Driver Loafers

Extended Sizes
Rated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 stars(55)

Polo Ralph LaurenMen's Alston Plaid Penny Loafers

Internet Exclusive
Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(2)

VionicMen's Uptown Suede Penny Loafers

Internet Exclusive
Extended Sizes
Rated 4.7857 out of 5 starsRated 4.7857 out of 5 starsRated 4.7857 out of 5 starsRated 4.7857 out of 5 starsRated 4.7857 out of 5 stars(14)

Polo Ralph LaurenMen's Anders Suede Penny Loafers

Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(2)

Flag LTD.Vincent Woven Leather Huarache Penny Loafers

Dillard's Exclusive
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(2)

Marc NolanMen's Adler Croco Embossed Leather Penny Loafers

Internet Exclusive
Extended Sizes

G.H. BassMen's Larson Weejun Leather Penny Loafers

Internet Exclusive
Only size 9 available
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

To Boot New YorkMen's Zenith Woven Penny Loafers

Internet Exclusive

Johnston & MurphyCollection Men's Taylor Suede Penny Loafers

Internet Exclusive
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Johnston & MurphyMen's Cort 2.0 Colorblock Croco Embossed Leather Penny Loafers

Internet Exclusive
Extended Sizes

COACHMen's Declan Suede Penny Loafers

Internet Exclusive

Steve MaddenMen's Natan Leather and Raffia Dress Penny Loafers

Internet Exclusive
Extended Sizes
Only size 9 available

Steve MaddenMen's Halian Leather Lug Sole Penny Loafers

Internet Exclusive
Only size 10.5 available

Marc NolanMen's Adler Pebble Leather Penny Loafers

Internet Exclusive
Extended Sizes

Marc NolanMen's Calum Floral Embossed Leather Penny Loafers

Internet Exclusive
Extended Sizes

Bruno MagliMen's Lastra Leather Penny Loafers

Internet Exclusive
Extended Sizes

Marc NolanMen's Del Mar Pebble Leather Contrast Trim Penny Loafer Mules

Internet Exclusive
Extended Sizes

VionicMen's Uptown Leather Penny Loafers

Extended Sizes
Rated 4.7857 out of 5 starsRated 4.7857 out of 5 starsRated 4.7857 out of 5 starsRated 4.7857 out of 5 starsRated 4.7857 out of 5 stars(14)

Marc NolanMen's Calum Leather Penny Loafers

Extended Sizes

Kurt Geiger LondonMen's Brompton Leather and Haircalf Penny Loafers

Internet Exclusive

Marc NolanMen's Adler Lizard Embossed Leather Lug Penny Loafers

Internet Exclusive
Extended Sizes

Johnston & MurphyCollection Men's Taylor Leather Penny Loafers

Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Johnston & MurphyCollection Men's Baldwin Nubuck Penny Loafers

Internet Exclusive
Rated 2.0 out of 5 starsRated 2.0 out of 5 starsRated 2.0 out of 5 starsRated 2.0 out of 5 starsRated 2.0 out of 5 stars(1)

Marc NolanMen's Abe Suede Penny Loafers

Internet Exclusive
Extended Sizes

G.H. BassMen's Larson Color Block Weejun Penny Loafers

Internet Exclusive
Extended Sizes
Only size 11 available

Marc NolanMen's Abe Suede Penny Loafers

Extended Sizes

Marc NolanMen's Calum Leather Rose Penny Loafers

Internet Exclusive
Extended Sizes

FryeMen's Tyler Flex Suede Penny Loafers

Internet Exclusive
Rated 3.6897 out of 5 starsRated 3.6897 out of 5 starsRated 3.6897 out of 5 starsRated 3.6897 out of 5 starsRated 3.6897 out of 5 stars(29)

TaftMen's Luke Leather Penny Driver Moc Loafers

Extended Sizes
Rated 4.3333 out of 5 starsRated 4.3333 out of 5 starsRated 4.3333 out of 5 starsRated 4.3333 out of 5 starsRated 4.3333 out of 5 stars(6)

Marc NolanMen's Del Mar Pebble Leather Loafer Mules

Internet Exclusive
Extended Sizes

Ted Baker LondonMen's Parliament Suede Penny Loafers

Internet Exclusive
Extended Sizes
Only size 7 available

ECCOMen's Soft 7 Suede Penny Loafers

Extended Sizes

Bruno MagliMen's Raging Penny Loafers

Internet Exclusive

TaftMen's Luke Suede Penny Driver Moc Loafers

Internet Exclusive
Extended Sizes
Rated 4.2857 out of 5 starsRated 4.2857 out of 5 starsRated 4.2857 out of 5 starsRated 4.2857 out of 5 starsRated 4.2857 out of 5 stars(7)

ALDOMen's Keifer Leather Penny Dress Loafers

Internet Exclusive
Extended Sizes

Bruno MagliMen's Leather Tonio Slip On Penny Loafers

Internet Exclusive
Extended Sizes
Only size 11 available

TaftMen's Jack Floral Jacquard and Leather Penny Loafers

Internet Exclusive
Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(2)

FryeMen's Tyler Flex Distressed Leather Penny Loafers

Internet Exclusive

Marc NolanMen's Del Mar Pebble Leather Penny Loafer Mules

Internet Exclusive
Extended Sizes

ALDOMen's Keifer Leather Studded Penny Dress Loafers

Internet Exclusive
Extended Sizes

Johnnie-OMen's Clubhouse Penny Loafers

Frye Men's Tyler Penny LoafersMen's Tyler Penny Loafers

FryeMen's Tyler Penny Loafers

Internet Exclusive
Rated 3.7273 out of 5 starsRated 3.7273 out of 5 starsRated 3.7273 out of 5 starsRated 3.7273 out of 5 starsRated 3.7273 out of 5 stars(22)
  • 123 Items
  • 1
  • 2
  • Next Page
  • Last

Customer Service

  • Contact Us
  • FAQ, Notices & Policies
  • Product Recalls
  • Returns
  • FAQ, Notices & Policies
  • Product Recalls

Dillard's Credit Card

  • Apply for a Dillard's Card Apply for a Dillard's Card
  • Pay Bill / View Credit Account Opens a simulated dialog
  • Dillard's Cardholder Benefits Dillard's Cardholder Benefits

Contact Us

  • Call 1-817-831-5482
  • Monday-Friday: 7AM-9PM GMT-6
  • Saturday-Sunday: 9AM-7PM GMT-6
  • Contact Us Via Email

More Ways To Shop

  • Registry - Wedding, Baby, and Gift
  • Gift Cards
  • Store Locations
  • Change Country
Stay in Touch.

Sign up for emails and get updates about
new products and the latest trends!

We Are Hiring!
Join our team
Click HERE to learn more
Be a Mobile VIP!

Sign up for texts and be the first to know
about upcoming sales and great offers.

We use certain tools to capture data related to when you open our messages, click on any links or banners it contains, or make purchases.

  • InstagramOpens Dillard's Instagram in a new window
  • FacebookOpens Dillard's Facebook in a new window
  • PintrestOpens Dillard's Pinterest in a new window
  • Twitter/XOpens Dillard's Twitter/X in a new window
  • YouTubeOpens Dillard's YouTube in a new window
  • TikTokOpens Dillard's TikTok in a new window
  • SnapchatOpens Dillard's Snapchat in a new window
  • Site Map
  • Terms Of Use
  • Terms Of Use
  • Dillard's Privacy Policy
  • Dillard's Privacy Policy
  • California Transparency in Supply Chains Act
  • California Transparency in Supply Chains Act
  • Careers
  • Investor Relations
  • About Us

Prices and sale offers may vary by store location, including Dillards.com, and are subject to change. © 2025 Dillard's

***