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 ...
Reviews
5.0
32 ratings
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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.
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Pete · July 10, 2026
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.
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Customer · July 8, 2026
Man i saw the comments and they do run big i may have 2 return them for a size smaller but they are beautiful