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Since you've never normally wear lipstick i'd stick to something close to your natural lip color. That way it's not a huge shock and your lip color doesn't become a distraction.
this may help too: http://styles101.homestead.com/face_lips.html
It depends on:
skin color
hair color (blonde vs brunette vs redhair)
color of gown (white vs ivory)
type of ceremony (religious vs civil)
type of gown (modern vs vintage)
type of reception (formal vs not formal)
color of flowers (warm vs cool shades)
but most of all it depends on your personality!!! If you are meek/shy don't use bold colors, if you are happy/energetic don't use "tame" colors.
Maybe start trying out tinted chapsticks? They're cheap (cheaper than some lipsticks), nourish your lips, and give you a chance to figure out how much (or how little) color you want.
There is only one rule to follow regarding skin tones and colors:
Warm skin tones look best in warm shades and cool skin tones look best in cool shades. If a warm skin toned person wears cool colors, it will make them look very washed out and sickly, regardless of how much they may like the color in general. The same applies if a cool toned person wears warm colors.
The other factors listed above (hair color, clothing color, color of flowers, etc) do not make one bit of difference. You can have two blonde women with completely different skin tones and they cannot wear the same colors, no matter what some people may think.
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.... with each skin tone?
I have a rich olive skin tone. I never ever EVER wear lipstick, but I am considering it. I'd love to pull off some shade of red, but I don't think I have the guts!