@rbb - so glad to see a kindred spirit! I know for us artists(but I don't know if you're one too)we have to be creative in our clothes because we simply don't have the money LOL! Like you, I'm not a huge fan of shopping, especially these days as so many clothes are of appallingly poor quality. It's really taken a nosedive over the last few years - the crap is even ending up in the thrift and second-hand stores just as I feared it would, making it that much harder to find decent stuff.
I totally agree you about noticing hair first, and that a crappy haircut can ruin the best outfit, seriously.
I love my haircutter and have been going to him more than 7 years now here in San Francisco. I found him through the local Yelp. But he's a genius with any kind of hair, and color to boot. If I ever decide to transition out of coloring, I'd enlist his help!