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.