Red lipstick is pretty unforgiving in terms of staining the skin, so I always use a lip brush. The lip brush pictured above is new to me, my aunt sent it. It's from a brand called Savage Jenny, which looks like it sells amazing cosmetics in general. I suppose their lip brush is so good because their lip product comes in pots. Totally going to try them at some point. Anyways, lip brushes are essential because they give you an excellent degree of control. Look for one that is relatively stiff with a decent point at the end for a precise edge.
The lipstick itself should be as red as possible. Think fire truck. I'm using M.A.C. Ruby Woo here because I find a matte colour looks nice on stage, and you can always add gloss on top. The lipstick itself can be pretty drying, so wearing some lip balm underneath never hurts.
So: How to Apply Red Lipstick
The first thing to do when applying red lipstick is to define the cupid's bow. Outline it with the pointy part of the brush and cut yourself short on the sides of the lips. It's easier to fill out the lips than it is to remove red lipstick. From there, add short lines to determine where you want your top lip to be filled to. Then, thicken the line.
From here, I normally line my bottom lip because it gives me time to decide if I like the look of my top lip. Line the bottom-most part of your bottom lip that you want to have lipstick on it. From there, fill in the bottom lip. This part is pretty easy-- I personally use downward strokes. After, fill in the top lip.
I don't use a lipliner because for whatever reason, lipstick does not run/feather on me. I'm not complaining in the slightest... but if it does for you, line your lips first with the same general technique for the top lip as shown above.
Hope you liked this post! I'm going to try to get into more cosmetic/tutorial/product based posts again. Let me know if this is how you apply your lipstick.