1) Do not hold onto items with stains, holes, ill-fitting, or have not been worn in two years; exception to this is "event-type" clothing.
2) Edit your wardrobe quarterly to help decide what new items to purchase throughout the year.
3) When deciding to keep-or-toss an item; put it aside for 24 hours and see if your answer is any clearer for you; 95% of the time you will donate it.
4) Do not fall prey to the thought of "I will wear this once I lose 10 more pounds". This piece is taking up prime real estate in your closet, and trust me, if and when you lose 10 pounds that is not the piece you will run to wear. You will want to reward yourself by going shopping!
5) Even though items that you have had for a few years may still be in good shape make sure the style, silhouette, and fit are still on-trend for now. Check the rise of a pant, the bagginess of a pant, the fit of a blazer, etc.
6) Do not hold onto items that have an emotional tie to it, it is a gift-guilt piece, or was on sale but you have still not worn it.
7) If having a hard time deciding to keep or donate an item, ask yourself the following questions: Do I love it? Is it still in style? Does it flatter my body? Does it fit my current lifestyle? Is it in good condition? Is it comfortable to wear?
8) If you are having a hard time deciding to keep or donate a piece, usually that means get rid of it. When in doubt, get it out!