Solve my hair dilemma

I'm having kind of a love/hate thing with my hair right now. I've managed to grow it out the longest its been in decades, and on good hair days, days when it's not so hot and humid that I can't be bothered to do anything beyond slapping it up in a hair clip and pinning it the hell out of my face, I have to say, it's pretty, and I love it (and before you go judging me for calling my own hair pretty, first know that it took me more than thirty years to be able to refer to myself as pretty in any context, and to stop accusing other people of lying when they used that word in reference to me, kthx).

But, it's not very hip. It's long, and curly, and I like my bangs, but other than that it doesn't have a lot of style. And like I said, half the time it's clipped up on top of my head anyway. Also, instead of going grey, I'm going white, and while the white:light auburn ratio is still low enough that I can pass it off as highlights, it's making me want to do something a little more extreme, color-wise, such as going either Lucille Ball henna red or light reddish blonde. I just don't think my current long, curly, shapeless 'do is suited to extreme color in either direction.

The main thing is, I haven't had a ton of luck with local stylists. I've never had one give me a hair cut I loved more than once (well, there was one who always did a fabulous job, but I lost track of her years ago), and I haven't found any that know what to do with curls other than flat-iron the hell out of them. The gist of which is that I love my long hair too much to give it up for anything less than fabulous, and I don't trust any local stylists to give me fabulous hair. The best they can do, I expect, is Stylish Mom hair, which, no. Maybe once I actually AM a mom, but for now, no.

Even so, I'm considering biting the bullet and getting it chopped. Part of me wants so badly to have cool, stylish, hipster hair. But then there's the part of me that loves having long curls and loves to be ultra-girly. And this, dear readers, is where my pole (tee hee!) poll comes in. Over on the sidebar, just two clicks will tell me which YOU think is better to have: pretty hair, or cool hair. Because I don't dare hope that I could ever find someone capable of giving me both at the same time.