I have slowly fell in love with lipstick. I used to never wear lipstick, I thought it was a pain to deal with (I still believe it's inconvenient). But I was bored with my typical go-to look, so I started with Mac's Cremesheen Peach Blossom; it's very similar to my natural lip color, meaning it was in my "comfort zone". It's still one of my favorite colors, I wear it to work at least once a week. After purchasing Peach Blossom I used Mac's recycle program, Back to Mac (turn it six empty Mac products for a free lipstick, lipgloss, or eyeshadow) to test out new colors. And here I am today still figuring out which colors I like and which I wish I hadn't bought.
When I first started to wear colorful lipsticks, it was a challenge, a very big challenge. After I applied my lipstick, I felt like I looked like a four-year-old... quite messy to say the least. So, I made a trip to my local Mac store for some coaching. I asked one of the makeup artist how to apply lipstick with clean lines, basically so I wouldn't look like a clown. She told me the key to wearing lipstick is applying lip liner (who knew, I always thought lip liner was for old ladies), yup that simple. She helped me apply liner then lipstick, the difference was immense. Today when I purchase lipstick, I try to make sure to grab a liner as well. I have a few from Mac, but I love NXY liners, they are much more affordable and work just as well as the pricey ones.
Mac Rebel (very light) w/ Mac Magenta lip liner.
NYX Power with NYX Merengue Butter Gloss
One last tip... If your lips are dry and you're struggling applying lipstick, try e.l.f.'s Lip Exfoliator for a soft clean base.