The Perfect Red Pout

This picture above reperesents a pretty decent guideline to your perfect red pout, but this doesn't mean you shouldn't try every red shade you like and see how you feel about it - instead of just going off of your skin tone. :P

When buying a lipstick here’s an easy way to gauge what works: Rather than swatch colors on your hand, dab on a fingertip and hold it up to your lip. Or apply the color (if possible) and snap a selfie. If the lipstick looks jarring to you, it will to others, too.
Why a fingertip?
Because it has more pigmentation - just like your lips do. =)

Opposed to what they say in this picture above, some say these are the rules you should follow:
For Fair Skin

If you have fair skin, consider a shade with a touch of orange in it to brighten your complexion. I know it works for me. Think tomato red to coral red.
For Dark Skin

Cool reds, devoid of orange undertones, are the most complementary on dark skin. In general, look for shades with a blue, almost plum, cast (as in, deep cranberry to light crimson). Remember, dark colors can be deceptive in the tube—coming out sheerer than expected—so when possible, test on skin before investing.
For Medium Toned Skin

Everything in between. ;) So not too orange-y, not too plum-ish, more a true red with a possible pink undertone.
Lip Tips
Still slightly overwhelmed by your options?

Consider a “universal” red, one with either violet or yellow undertones (considered neutral on the color wheel, these colors blend with any skin tone). Yes, it’s a bit challenging to detect such subtleties, but even an untrained eye can usually gauge a tinge of yellow or purple. Before buying, if possible, take a red lip color to a window so you can see it in natural light (fluorescent store lighting can make reds look more blue-toned). When in doubt, it’s better to buy a shade that seems slightly too bright, because you can always blend it or blot it to make it sheerer and more wearable. (Sheering a color out—makeup artist-speak for blotting with a tissue—to lessen the intensity of the pigment is also a good way to ease into reds, if you’re not used to seeing yourself in them.)
P.S.
You can honestly wear whatever you feel is best for you. These are just some helpful tips you can choose to implement - if you wish. =)
P.P.S.
If your teeth aren't very white - steer clear of pink lipsticks!
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