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I'd say you don't necessarily want it to match, you just want to make sure it doesn't clash. For instance, if you're wearing an olive green dress, that wouldn't be the day to wear a blue eye shadow look, you might try bronze instead.
Neutral shadows are handy to have because they'll go with any clothing, bright colors and all. On the flip side, neutral clothes are handy to have because they'll allow you to wear any eye shadow, bright colors and all.
If you're in doubt about whether or not a particular eye shadow is going to blend well with your outfit, you can always tone it down with a second neutral shadow. I do this all the time. If I'm wearing a plum or violet shadow on my lid, I'm probably also wearing a cocoa shadow in my crease. If I'm wearing an icy blue shadow on my lid, I have a slate shadow blended into the crease.
One more note, I find it easier to blend makeup and clothes without doing the matchy-matchy thing if I do my makeup first, then find something in my closet that won't clash. If I pick out my clothes first, I can't seem to resist grabbing a matching eyeshadow or a matching lipstick.
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