In my 26 years, I have never had a hair cut that I liked. I've had some I think are okay, and some that made me look like a Raggedy Anne that's stuffed in a light socket, but most of the time I come out of the salon thinking, "Well, it'll grow back."
There are a couple of issues:
1) I've always been overweight. And when a curly-haired overweight woman walks into a salon, the first thing they want to do is straighten your hair. If you insist that you want to leave your hair curly, they frown and then give you what I like to call the "Fat Girl Special." Straight across the shoulders, no shaping, no layering, no effort. This is basically the, "Well, at least it'll look even," concession. I hate it. I hate it all the more when I go in and say, "Let's do something fun," and they STILL give me the Fat Girl Special.
2) My hair is a bit weird. If I air-dry it with some product, it's usually about a 3a (for people familiar with the patterns chart). But if I brush it out, it doesn't frizz like normal curly hair. Instead, it'll submit itself into a nice 2a/2b. Which means, as I've tried to tell countless hair dressers, that I need something good for both curly and wavy hair because my curly hair doesn't last for more than a couple of days, and I need to be able to brush it out to have it last another 3 before washing.
Now I have tried to tell this to hair dressers. I've even brought in photos on several occasions. They sort of nod and either give me horrendous layers or the Fat Girl Special. Or, worst of all, they don't listen to my request NOT TO FLAT IRON (I'm trying to keep my usually-dyed hair as healthy as possible) and then flat-iron my hair and give me a cut that only looks good when straight.
So I put it to any GTers in the know: what can I do to get a hair cut I don't hate? Do I like for a particular type of salon, or stylist, do I need to say something different? I've taken to cutting my own hair on and off for the last 6 years or so because I'm so frustrated, but I know I'm not a hair dresser and it doesn't look great.
ETA: A quick note. I like my hair long and short. I just don't like it "medium." So my "ideal" hair would be this and this equally: