2: Purge, purge, purge
Now turn your attention from your closet to those piles on your bed. Sort them into three categories: toss, give away, and keep.
Toss: "Anything that's damaged beyond repair or too worn out to donate with a clear conscience should go into the toss pile.
Give away: Pieces that are out of style, don't fit (that includes those size 4 jeans you've been holding onto for years), or that you no longer like get thrown into the giveaway stack," says Fascitelli.
Keep: "The keep bin is only for clothing that meets three criteria: You love it, it fits you now, and you've worn it within the last year and know you'll continue to wear it." If you think you'll be indecisive about which pieces should go in which pile, enlist an unsentimental friend to help. Jettison the giveaway items either by donating them to a charity (try dressforsuccess.org) or selling them at an online auction site, like ebay.com.