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1. Take inventory of what you have. If you have children, tackle this job one child at a time. Make a list of all tops, categorizing them separately - short sleeve, long sleeve, t-shirts, dressy, dressy casual, etc. Do the same with bottoms - shorts, capris, jeans, skirts, dress pants, etc.
2. While going through the closet, start a donation pile and a throwaway/rag pile and a giveaway pile for clothing you want to pass on to specific people.
3. Make a list of all the possible outfits, both summer and winter.
4. It will become obvious which articles of clothing have no matches or matching accessories - shoes, socks, jewelry, belts, etc.. Make a shopping list.
5. NOW it's time to shop! If you are shopping for your children, make back-to-school shopping a fun event. If you can, take one child at a time, have lunch together, and make it a special day.
Even though this process takes a while, it is far more productive. You may discover outfits you never considered, you'll clear the closet of unwanted items, and your shopping will be intentional rather than haphazard, which will likely save you money. And you and/or your child will have a list of outfits to wear - especially helpful on those days when choosing an outfit seems overwhelming!
More on family organizing:
Managing Paper, Part 2
Keeping Things Organized - Family Five Minute Challenge
Creating Routines and Systems