Too many, or not enough?

Along they lines of personal style, I have been reflecting that I really may have too many clothes. Not that I've done an actual count, or anything. I have five large drawers, six medium drawers and a closet. And If I amazingly get it all clean at once, It doesn't all fit where it goes. But Most of it is second hand! So that means it is okay to have more, right?
One year in College, I waited until the neighbor girls moved out, and then moved my clothes into their empty room for packing. My clothes took up one whole side of the room. To this day I don't know how I got it all in the drawers and tiny closet at school.
In Junior High, My dad made us some really big drawers because the dressers we had didn't accommodate everything. So I guess this problem goes way back. It's probably my mom's fault. I will probably need years of therapy if I want to get over this. And I would definitely rather have tons of cheap clothes that years of expensive therapy. I mean, they're just clothes!
As I sit here typing, though, It occurs to me that I probably don't have too many clothes, I just don't have as many places to wear the nice ones. As I mentioned on Friday, it's mostly jeans and casual tops for me. When I was a librarian, I had Lots of chances to wear lots of other things. I wore skirts all the time and got compliments on my fantastic blouses and necklaces every day. I got a chance to display my somewhat unconventional personality through my outfit every day. And I bemoaned that I couldn't wear my jeans to work. Sigh. I guess I can't be satisfied.
Maybe I just need some more casual tops?