I tend not to get my hair cut often. I usually keep it long and layered and I just need a trim when I finally go, so it is really difficult for me to justify spending a lot on a haircut. I had been going to a drop-in place near work that was better than Super Cuts but not really that great after all. Every time I went in, my hair was cut a little worse than the time before.
Just before BlogHer in July, I went back to a real salon for a real haircut and some sideswept bangs. I went to the woman who had styled my hair for my wedding. Turns out she is great at updos and shitty at cutting hair. At BlogHer, when I had my hair styled by Anna from Lukaro Salon in Beverly Hills, she actually had to cut my bangs to fix them before she could style them.
Even though I knew I'd had a bad haircut and needed another one, I refused to get another hair cut because I'd just had one and I didn't want to pay for another one. It would feel like I was paying double for a haircut, which is ridiculous reasoning. Now that it's been about three months, I could finally justify getting my haircut again. I decided to quit being so cheap and I paid $95 (plus tip) to have Anna cut my hair. It was worth every penny.
I think the $100 mark is about where it stops, though. I once paid $250 for a hair cut with Jonathon Antin (before his ridiculous, narcissistic reality show, after which he raised his rate to $500) and it was so not worth the money.