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This is the most difficult part. You have to be hard on yourself and really only keep the items that you are actually going to wear. Make sure the pieces you keep fit your lifestyle (that includes your job) and personality and are in your current size. To make the process easier, divide your items into these categories:
Donate everything in this last category to your local shelter or an organization like HousingWorks or Goodwill — it’s the best feeling knowing that someone else can take advantage of the clothes you're not wearing anymore. But don't be afraid to find the trash, too. Anything that is worn out, ripped, or stained should be tossed.