My son's dresser has 4 drawer--we have bottoms in one drawer, tops in another drawer, and socks/undies/pjs in another drawer (the top/highest drawer is for my use and has things like sheets in it). My daughter's dresser has 6 smaller drawers, so we split long sleeve and short sleeve shirts, and also split pjs and socks/undies/tights (one drawer for me still, its' got clothes that are a bit too big). Dresses and button-up shirts are in the closet. We don't have that many clothes that are not in circulation, but I like big clear plastic bins that can go in the closet--easy to see what's inside.
These are different ways we've gone about balancing our daughter's dress-herself needs:
--"You choose a (long sleeve/short sleeve) shirt, and I'll choose the pants today." (If she chooses first, I can choose a coordinating color.)
--or alternately, "Choose a pair of pants and I'll choose your shirt."
--pick out two outfits and have her choose between them
--"You can choose whatever you like to wear today, but it must be pants and long sleeves (or shorts and short sleeves)." ... and don't worry about the color combination, she'll enjoy the independence and it doesn't really matter if her colors don't match for a day.
--"We need to pick a dress today. Which three do you like?" and then I choose from one of those she picked out.
We got to the blessed point where I could say "go get dressed, it's going to be cold today," and she would come back in appropriate clothes. Now my daughter's 6 and has lately been wanting me to pick her clothes again before she gets dressed, and I'm thinking, "just get dressed already!" One day you'll enjoy that independence of hers! :)