How to know if I would look good as a blonde? And how blonde?

I'm slightly tan. I'm german and irish, but for some reason slightly tan skin runs in my family. I'm not tan enough to look spanish, or indian. I would say my skin tone matches Nicole Richie's(She's blonde ) My natural hair color is a chocolate brown. I have brown eyes, but I often wear blue or light green contact lenses. I'm 16, and I've always stuck with dark hair colors, like browns, black and even some dark reds. But I've had a blonde undercoat for a while and I really like it.

So, should I give blonde a try? And what shade of blonde? Any advice? I would be going to my hair dresser to get it done.

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