Here was my process: It's probably a little different for everyone so feel free to add your suggestions in the comments, but I think it's a good starting point.
1. Choose a charity to donate to and plan a time to stop by. I like to start with this one because if I don't I end up with my "to be donated" bag sitting around for weeks (ok, months) on end. It's also a good motivator to know it's for a cause. This time I did something a little different and signed up for my first clothing swap!
2. Do your laundry. Having everything clean and put away helps you to be thorough and really assess what you own. I also pulled all of my winter clothing out of storage so I could see what needed to be cleaned and replaced.
3. Sort everything into four categories: keep, mend, toss and donate.
• Keep: If it's in good condition, it fits and you'll actually wear it.
• Mend: If it's wrinkled, stained, dingy or has a tear that can be repaired.
• Toss: If it's ripped or stained beyond repair.
• Donate: If it's in otherwise good condition but doesn't fit or you just don't wear it.
4. Place the keepers back in your closet, take the mends to the cleaners/tailor/cobbler, and finally get ye to the nearest Goodwill (and don't forget to ask for the receipt).
Once your closet is edited down and cleaned up you can get a much better sense of what you actually have and need, and you'll save yourself time in the mornings when you don't need to sift through everything else. If there were things in my toss pile that I loved so much I just plain wore them out, finding a suitable replacement usually goes right to the top of my shopping list.
Image: Matchbook Mag