I'm still trying to figure out my sense of style with regards to loafers. Since I started buying Allen Edmonds's shoes a few years ago, I have mainly focused on dress shoes and boots. I bought the McGraws because they seemed to be about as versatile as a loafer could get, but something about the last makes them blister my feet if I wear them without socks, or if I walk to far in them (I could wear them for a full day of playing tourist, for example).
I'm a 36 year-old lawyer. I love how the Graysons look, but I mainly see them on older men -- people at the partner/supervisory level, and I'm worried about looking like a parvenu!
Also, tassel loafers seem to be particularly popular in #8 shell. Would it make sense to hold off on burgundy pair finds its way to eBay or the Shoebank?
Interesting on the comment about that last tearing your feet up. I typically don't wear any of my nicer shoes without socks, but instead use invisible socks because I do love that sockless look... especially with loafers. I find that the invisible socks both protect my feet and the shoes (my feet sweat a lot). Apparently the last that shoe is made on is roughly the same one as the 97 (toe box is slightly different) used for the Grayson, so just keep that in mind.
I actually think the Grayson is more of a "young mans" tassel loafer if you compare it to something handsewn like a Maxfield for instance. The sleek look that a lasted loafer can give lets you pull the tassels off (if that makes any sense, it does to me at least). #8 is definitely awesome and if you can hold off and find a pair that you like, that would be a great way to save some coin.
If you were going to go with some handsewn, I would forgo the tassels.