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How do you begin to pick a hairstyle?

I'm not much a glamorous gal, I've never done more than put my hair up in a bun. I've tried to curl it a few times but it wont hold a curl at all. I wouldn't know what would look good on me just by looking at pictures.  What I really want is to talk to a professional who knows what would shape my face well and what to do with my hair type that wont hold a curl. Is that possible? How does one go about doing that?
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