I don't know about you, but every time I watch an episode of Mad Men (which is often) I always wonder, Why don't I wear lipstick more often? Is it a generational thing? Is lip gloss a suitable replacement? Will it end up as tooth lacquer?
My very first lipstick was a regrettable rusty-matte color by Revlon called Toast of New York. I opted to debut this shade for my 8th grade class photo. (Paired with thick and pale foundation, I looked anything but toast-worthy. Not a trend I'd care to resuscitate). Often the troubles that seem to accompany lipsticks can seem to outweigh the benefits, but I've found a few brands and colors that you could toss into rotation, after watching Mad Men or otherwise.
Pinks: Cover Girl Parisian Pink No.545, Revlon Sassy Mauve Creme No. 463, LipFusion Plumping Pencil in Pretty.
Plums: Benefit Silk Lip Pencil in Sangria, Nars Afghan Red (it's very plum)
Reds: Note, these are t-r-i-c-k-y. I have found that layering a few of the aforementioned plum choices with reds create the prettiest and most glamorous lip: Yves Saint Laurent Rouge Volupt in Red Muse, Revlon Love that Red.
Before applying lipstick I sometimes brush my lips gently with a wet toothbrush. Do this quickly as the mere sight of this behavior can lead to embarrassing conversation. Use a small bit of chapstick to prep and bonus points for applying a small dab of foundation to create an even lip canvas. Smooch!