It is tempting to think "okay, here are three things that work. I will buy seven of each of them and be done with it."

Yes. And so when I found some nice t-shirts that were appropriate for work, I bought them in a bunch of different colors and planned to keep buying them--only this year they changed the style (while keeping the style name, to confuse) so now I have to go through that all again. :-(

It's not so much that I can't find things that I think look nice on me, it's that finding comfortable things that look good *that I can afford* is really time-consuming and so I try to avoid the search.