Black Leather Penny Loafers, Hand-Sewn Since 1946
The Classic Dan is Sebago's original men's penny loafer: a low-cut, beefroll-style slip-on built from smooth corrected grain leather and hand-sewn by a single craftsman, pair by pair. Named for one of Sebago's founders, it has anchored the Cityside collection for more than 75 years.
Dress it up with tailoring or wear it down with denim. Either way it earns its place in the rotation.
Materials and Construction
- Upper: 100% leather
- Outsole: 80% leather, 20% rubber
- Lining: Unlined upper with leather sock lining
- Construction: Hand-sewn beefroll penny loafer
- Made in Mexico
How Do Sebago Loafers Fit?
Sebago loafers run about a half size large. If you normally wear a 9, order an 8.5. They also run narrow through the midfoot and toe box, so if you have a wider foot or usually size up for width, choose the Wide.
The leather feels firm out of the box. Wear them with socks for the first few outings. As the leather softens it molds to the shape of your foot, and the fit becomes yours specifically.
We ship to all 50 US States, Puerto Rico and US Virgin Islands. Orders ship 1-3 days after the order is placed during normal business hours (Monday – Friday), excluding postal/federal holidays.
Returns
Sebago has a 30 day return policy for all products that are not customized.
S
Fit: Runs Big
Love the quality and look of the shoes. Unfortunately they are way too big for my feet. I am a size 8.5 with wide feet so I usually have to move up to size 9. I bought a 8 wide but is still seems to be 1-2 full sizes too big. This was the smallest size at the time of purchase so I wasn't able to try smaller sizes. I will need to return these.
L
Sebago blew me away. The quality control is really good. I couldn't find any flaw at all. The packaging is really nice too. Each loafer was wrapped in its own felt bag. Very much worth the price.
I tried GH Bass beforehand, and had to return them due to terrible quality control.
P
I must admit that I tried four sizes before landing on the best fit, but it was worth it. Their return policy made it pretty easy to deal with, too. They are high quality, classic cool, highly versatile, great shoes. It's hard to find things like this these days.
I recommend half size down from your normal sneaker size and Wide, the regular is quite narrow especially around the midfoot and toebox. And yes, they do mold to your foot as they break in. I was a little worried about heel lift on the Wide at first, but when the sole softened and the rest of the shoe molded around my foot they became just right.
R
Man i saw the comments and they do run big i may have 2 return them for a size smaller but they are beautiful
R
The shoes are fantastic. I wish there could be information about the size in millimetre in addition to the shoe number. This because the shoes are bigger than normal size and it is also recommended to go down one size one ordering. This will help to get the right fit.
A
Excelent shoes
G
Love my Classic Dan! It lives up to your reputation!
A
My shoe bugs are flawed. I contacted the customer service but they didn't respond to me :(
R
Love these shoes for more than 25 years!
J
For perfectly thanks to grant’s help
A
read your mail Service department, My Order shipped on 1.22.2026, and as of this morning, 2.5.2026, I have not recieved them
I have asked for a refund, get on it.
J
I am disappointed with the customer service. The shoe was shipped and left on my son's Boston Brownstone steps by the shipper who didn't ring the bell or leave it in the Lobby where all shipments are left securely. Sadly, no one will take responsibility, and I paid $250 for a pair of shoes not received. In a big city no one leaves a box on the steps of a building. My son works at home so it could have been prevented.
K
Love the shoe and craftsmanship!. I just wish the toe box could be a little wider.
J
Buen artículo y calidad.
L
very comfortable shoes
A
Great fit, sized down 1/2 and went with wide.
M
Love the fit and they are the classic loafers I always wanted! They look great
A
Great shoe and fit
D
Everything I wanted. The leather smells lovely 🖤