Q: I'm finally getting around to cleaning out my closet, but I'm indecisive about what to keep. How do I make this process painless?
A: Painless, no. Ruthless, yes—you've got to be tough and thorough. My rules:
1. Allow an entire day.
2. Focus on the current season's clothing (in this case, you're probably confronting fall-winter).
3. Try on everything in front of a full-length mirror.
4. Be brutally honest: If it no longer fits your body or your life (or if you haven't worn it in two years), out. Your "keepers" will probably be classics with staying power. Here are the essentials for this time of year:
Jacket or blazer
Two dresses: one black, one wrap
Three pairs of pants: denim, tailored, day-to-evening
Skirt, whatever shape works best on your body
White shirt, preferably no-iron stretch cotton
Lightweight T-shirts and tops
Sweaters and knits
Four types of shoes: flats, daytime heels, boots, and evening