The tail is supposed to be long. The clothed version is a better example of this. Digitigrade or plantigrade, It doesn't matter to me I just felt like drawing him digitigrade.
Clothing (This applies only to casual, realistic clothing.):
Clothing is pretty much what I would wear. Hoodies, button-downs, cardigans even (nothing fugly). Things that go over shirts. Or whatever I'm not too picky now. Jeans, no shorts if it can be helped. Since I drew him digitigrade putting shoes on him seemed awkward. So as far as shoes go, Converse. Lastly the glasses are optional. I wear glasses pretty much all the time but I don't even draw them in half the time.