As a ballet dancer for many years, I thought of red lips as stage makeup and found it weird to wear it out in the "real world."
I suppose, it takes some growing up to be able to wear red lips with ease. In my early 20s with very little life experience, I felt like a little girl playing dress up when I would attempt red lips.
But now that I'm just a month and change shy of 30 and my ingenue state is rapidly slipping away, I'm feeling very comfortable with scarlet lips. I don't need a special occasion to wear red; I will put it on even when I'm just spending a Sunday afternoon shopping in Soho.
It helps that I've found my perfect red: Yves Saint Laurent Rouge Volupté in Red Taboo. It's a rich, blue-based red that stays put even after one glass of wine, two bottles of beer and a massive pot of mussels (true story). While it's not exactly cheap at $34 a pop, I think it is worth every penny. The texture is so rich and luxurious, and this particular brand keeps lips moisturized. I love it to pieces.