I've worn this look a lot (often Deb's way) and actually prefer it to a shirt-and-crew-neck combo, which looks a bit blah on me. The "winged" effect of the collar adds a little spikiness to the look--particularly good with short hair like yours, I think. I don't have many rhinestone necklaces, but have gotten a necklace effect by nestling a big brooch over the top shirt button, and sometimes even poking vintage clip earrings through the buttonholes of buttondown boy shirts. It's fun to play with, and you look terrific. Not Just Current Enough, and not Classic, but a new category--Thoroughbred Hip, maybe?