Red lipstick is kind of my ultimate pick me up. If I'm having a bad hair day or just generally feel like I'm not looking my best, it brightens everything up and becomes the focal point for my face, drawing attention away from the things I'm not feeling so great about. It's also a great confidence booster, in no small part because any time you wear it, you will be inundated with compliments. "Oooh, I love your lipstick!"
I know a lot of women who feel like they can't wear red lipstick, but I think it mostly comes down to picking the right shade and just getting used to having something that bold on your face. It doesn't have to be an all the time thing, but for special occasions the right red is a great tool for making you feel like a million bucks.
If you're unsure about which red is right for you, take a trip down the Sephora or you local beauty counter. When you find one that you think you might like, take it home and just wear it around the house for a little bit. (Pro tip, though - take it off before you eat anything you have to open your mouth up wide for. Red lipstick smeared all over your chin is an absolute bitch to get off.) Once the initial weirdness of looking in the mirror and seeing bright red lips wears off, you'll realize that you don't actually look like a clown and can make a better judgement about whether or not the shade you chose suits you.
For application, I think it's best to keep things straightforward and easy. I like to put a thick layer of balm on before bed, which softens my dry, chapped lips. In the morning (usually as the last step before leaving the house, since I'm prone to getting lipstick on my clothes if I put them on after), I'll prep my lips with a little bit of foundation, which evens out the color and provides a good base for the lipstick to stick to. I apply one coat of lipstick straight for the tube, blot, and repeat. Any wonky edges I fix with the pointy end of the lipstick; if necessary, a q-tip and a dab of foundation are great for correcting any little mistakes.
Because lipstick is such a subjective thing, I highly recommend finding a place where you can play around with different brands and colors, like Sephora, Ulta, or any department store. Personally, I'm really partial to Sephora brand lipsticks, particularly the Rouge Cream line. They wear well, leaving you with a nice stain even after you take them off, and the color is creamy and opaque without being overly drying. They also clock in at under $13.00, so it's only a few bucks more than most drug store brands. The color I'm wearing in the photo above is called Passion Red.
Sephora Cream Rouge Lipsticks