I was discussing my little style-crisis with a friend of mine, who is generally very chipper and weird and knows me very very well, despite our physical distance. Daily text volleys, you know. Anyhoo. She asked me a question that struck me-
"Well, what do you want your look to express?"
I have no clue.
I think the "not feeling or expressing emotions" is definitely the root of the "clothes are simply utilitarian objects" problem. I don't know what I want to express, because I don't actively try to express, well, ANYTHING.
I bet I'm expressing things, I just don't realize it. It's like my artistic style or writing tone- I don't see it, but everyone else can immediately identify the source.
If you had to dress me, based solely on my ramblings and your knowledge of my job, what would YOU pick?