Pretty scary, coloring your own hair, isn't it? I've been doing it for so long now that it doesn't bother me at all. Before I go any further, I should tell you that I do spend quite a bit of money (~$50) for a haircut. The problem was that if I added a color and highlights in with that I was spending about $110. Since I need to color more often than I need to cut I decided to go longer in between cuts (I get my hair cut about every 10 - 12 weeks) and color my own hair as often as I need to. Since I color my hair approximately every 4-6 weeks I estimate that this saves me about $500 per year. I actually get a lot of compliments on my hair color (thanks L'oreal) so I must be pretty good at doing it.
When I first started coloring my hair I used a non-permanent that would wash out gradually after 30 washes. This type of color tends to be fairly inexpensive (~$6/box) and fairly risk free. This allowed me to test different shades and decide on the one that I liked best. Since it washed out eventually I didn't get to upset if I choose poorly. Once I decided the shade that I liked I switched to the same shade in a permanent color. About a year or so ago I decided to try my hand at a color/highlight combination that L'oreal sells for about $13/box. I was a little nervous about the highlights at first but have found that it's super easy. The highlights are subtle enough (as long as you don't leave it on to long) that even if you mess up a little it's not really noticeable.
How do you save money on your cuts and colors?