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I usually don't match my makeup to my outfit.  Neutral tones for eye-shadows are best because they accentuate the features instead of hiding or overpowering your face.  Depending on the color of the shirt or dress that I'm wearing, I may accent my shadow in the crease with a minimal amount of that color.  With lip color, I choose a lipstick that compliments my face the best.  Red is my favorite color to wear; I own several shades and choose the one that best coordinates with what I am wearing that day.