Adam Glassman
Photo: Robert Trachtenberg
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:

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
  • Cashmere cardigan
  • Winter coat
  • Trenchcoat
  • 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
  • Three bags: day, weekend, evening