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Boring hair needs help

I'm bored with my hair color. I dyed it various shades of red for about a decade, recently transitioned back to my natural color only to promptly become bored of it. I need a haircut, too, so my hair will curl nicely again, but that's another story for another day. Help me, GT!. (photo below)


I've got some highlight things going on in there. You can see my skin tone in this pic:

So, what should I do? Darker?

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