Red lipstick looks good with you. Assuming that the person you are talking about is wearing the lipstick it would be on you rather than with you. Using the word with implies that the person just have the lipstick with them (it doen't mean they are wearing the lipstick).
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AnonymousIs this natural?Red lipstick looks good with you.Assuming that the person you are talking about is wearing the lipstick it would be on you rather than with you.