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How do you choose a flattering new hair color?

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OK, I'm not 'bout to go crazy and break out the bottle of dye :lol: , but I would like to maybe get a wig in a lighter shade. I am a #2 hair color, and have been wearing wigs in the same haircolor for a while now. Recently, I started wearing full wigs. I would like something lighter, like some #4, #8 and maybe even a miniscule amount of #6 thrown in for highlighting, but how do you determine if colors flatter your skin tone, especially when you're trying on a wig (if at all, I never do) in a dark bss and can't see what it looks like in daylight? My complexion is about Halle Berry's, eyes are darkest brown, almost black. I have thick eyebrows too though I think I would lighten them to complement the wig.
 
I like to use celebrities for inspiration. I've always stayed within the brown realm when I used to color my hair. But now I'm seeing some great looking colors and color combos on different celebrities. Also if you find a celeb with your skin color it helps.
 
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