I bought a pair of these penny loafers 30 years ago when they were still being made here in Maine. They still had wear in them minus the ability to "shine up" well but even still were good looking and my "go to" shoe with a jacket and blue jeans. This pair fit like bed room slippers after break in. I finally bit the bullet and bought a new pair knowing this pair was living on well borrowed time. This new pair is constructed the exact same way, in every detail, minus two nail heads visible in the soles. No big deal. My old pair was a 10.5 D and I ordered a 10.5 D. Understand that these shoes are true to size if you really understand what your shoe size is. If you have never owned a pair of these classic Sebago penny loafers you will be unhappy with the fit. Board the "pain train" and do the work to break them in and have the best shoes in your wardrobe that you have ever owned. Put on a pair slightly larger SOAKING WET socks than you plan to wear in reality. Use a shoe horn, put them on, and wear them a little bit everyday until they take shape to your feet. Trust me folks ... these shoes will fit like they are suppose to and fit like a glove after going this and also wear like iron, or so I hope, for another 30 years...but don't think they will feel any where correct straight out of the box, this is an unreasonable expectation from this QUALITY penny loafer! Leather stretches .... do the work and end up loving a pair of shoes that you will not want to take off. After a week of break in, I'm wearing my new loafers with thin dress socks and oft times sock-less and my feet are HAPPY!UPDATE: After having these shoes for a year, they are a complete disappointment. These Sebago's are now manufactured outside of the USA and are, sadly, cheaply built using inferior material and cost cutting methods. The leather soles have holes worn through to the inner liner and the sole actually split around the stitch seam around the toe area. The top leather finish "flakes" off at the flex points of the shoe which reveals leather beneath which can not be polished back to life and blend back in to the surrounding leather. It is a horrid look, light colored spider cracks and lines across the top of the shoe and sides. Taking these shoes to a cobbler for failure analysis, I learned that the color was "painted on" ( a process used now to cut cost) and not dyed through and then polished to a fine and lasting finish as they were back in past. Trust me..you won't live in these shoes for long at all. Go high end with a USA manufacture for your loafers and get 30 years out of them as these are not it! Sorry folks, for steering you wrong with my original review...