Red Lipstick, even though I'm afraid of it sometimes, because it can be really high maintenance, brings me joy when I finally find one.
Right now, I'm loving Dior Red Smile. It's a bright red that doesn't wash out my complexion and the formula hydrates, which is essential so I don't get that kind of dry drawn on looking lip that can age your face really quickly.
Here's Two Of My Tricks for Wearing Red Lipstick
Color in your entire lip with a flesh tone lip pencil. It works like primer, but without the price, and it's one less thing you have to buy, look for, or put away when you're done.
Apply one coat of lipstick as a base. Lay a tissue across your lips. The tissue will adhere to the lipstick and hold in place I promise you. Let the tissue rest for a moment covering your entire mouth - an outline of your lips should be visible through the tissue - then pull the tissue away. Wait a minute to let the lipstick dry down and then reapply another coat of lipstick. Even when the glossy second coat wears off a bit after a few hours the perfect outline and most of the color will stay through your day. Now that should brighten your smile!