How to be Smarter: I Feel Bad about My Neck by Nora Ephron is my most highly recommended book in a long while. It is a quick, smartly written memoir--an especially good read for people that are in love with New York City. How to be Prettier: Keep a pair of cheap street flats under your desk at work to wear to and from--something comfortable but more stylish than sneakers. Some good options: elegant white, black patent, and these are a favorite of mine.
How to be (less) Awkward: There are people in your life who you can eat a salad with your fingers in front of, and people in your life who you can't. Know the difference, and try to respect it.