How to be Smarter: How far would your salary go in another city? [An interesting reference point, even if you are not considering moving anytime soon]. How to be Prettier: A cap-toe detail on shoes continues to be trending this fall; this is the pair I've been wearing and loving lately [in black].
How to be (less) Awkward: Regarding small talk: "My favorite question is: 'What’s keeping you busy these days?' It’s useful because it allows people to choose their focus (work, volunteer, family, hobby) — preferable to the inevitable question (well, inevitable at least in New York City): 'What do you do?'" -- Great quote from this article on small-talk strategies.