I cut my hair really short about 4 years ago, just above my ears. I wanted to give it a whirl. Well it looked pretty cute when the stylist styled it for me, but since I am lazy and just wash it, don't even dry it, I comb it out a little that's all, it didn't look too polished on a daily basis. Plus it didn't really suit my face shape so well. Anyway, I felt less feminine with the short hair, it was especially a bummer when I would get dressed up. Also annoying not being able to pull my hair back in a ponytail. Sooooo I grew it out and now it is pretty long and I am very happy with it :-)
But I can see how short-short hair can be a great convenience.