Dooce blogged about a site called Rules of Thumb. Here are my favorites from the "Clothing" category:
Wait one year before throwing out a piece of clothing. If you haven't worn it in a year, you will never miss it.
When in doubt, overdress. It is easier to dress down than up.
If a person is poorly dressed, you notice the clothes. If impeccably dressed, you notice the person.
If you have to convince yourself that you want a particular article of clothing, don't buy it - you'll be adding another dust collector to your closet.
This last tip is my favorite. It's another way of saying, "If you love it, buy it. If you don't love it, don't buy it."
I would go even further and say that my personal clothes-shopping motto is, "Only buy something you want to wear out tonight." It's never failed me. I've quickly arranged dinners out so I can wear a new dress, skirt, top or pair of shoes that I bought earlier that day.
Edit: Here's another fantastic rule of thumb from the site - "Never go cheap on your bed or your shoes. You will be in one or the other your entire life."
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