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When wearing red lipstick you must consider the following things:
If you have red or warm hair do not try to match the color of your lipstick to your hair color. If your hair is a warm red, opt for a red that offers a contrast, for example a pinky red. If your hair is a violet red, opt for a true red or an orange red.
If your skin is cool and has pink tones you are most suited to a true red, avoid coral and orange reds. If you skin is warm and has olive tones you are most suited to an orange red or burnt orange red, but you will also look great in a true red.
Wearing red lipstick is not about matching your clothing. If you are wearing bright red, opt for a very different tone of red lipstick- perhaps a pinky red. Create contrast by not matching your reds.
Do not compete with your focal point. When wearing red lipstick keep the rest of your makeup simple, clean and fresh. Stick to either gold or silver tones for your lids. If you want to create another focal point, pick one area only; either create bold dramatic brows or create a cat eye with your liner.
Always remember that wearing red lipstick, in any tone, is about making a statement and being bold, so have confidence in your look.