Clothes that don't fit: If you've gained weight, keep the smaller-sized clothes that you'll get the most use from and work on fitting into them again. If you've already lost weight, don't keep a whole closetful of big clothes as though one day you're going to suddenly be struck fat; donate them.
Trend items: If you're waiting for something to come back in style, don't. Even if it does return, it will look dated—and so will you.
Special occasion outfits: The rule that says "If you haven't worn it in a year, donate it" is a fine guide for when to say goodbye.
Sentimental pieces: You say, "I really loved this jacket." I know you did. But if you haven't worn it in ages and it doesn't work with your other clothes, it's time for it to go away. If you're saving your wedding dress, be honest—do you have the space to store it? Do you have a daughter you're saving it for, and is it a timeless classic she won't roll her eyes at? If the answers are yes, keep it. If you're short on storage space, you have only sons, or your dress has puffy sleeves, lace, and buttons up the arms because you did a kind of Linda Ronstadt circa 1974 thing, give it to a thrift store or DonateMyDress.org, which provides formal wear to girls who can't afford prom or special occasion dresses.
Now that you have a closetful of clothes that you actually wear, organize them—all the short-sleeved shirts together, all the jeans together, etc. Do the same with your shoes. If you have the space, they can be kept on shelves so you can see them immediately. If not, try stacking shelves or hanging shoe racks.
This is an excerpt from Oprah Magazine by Andrew Mellow, a professional organizer. To learn more about Mr. Mellow visit VirgoMan.com