After Mrs. Jacks work clothes thread, I have been thinking about updating my wardrobe.

I am really interested in a wardrobe planning app that you could enter your clothes and then match them up to make outfits. I feel like my wardrobe needs a better balance of nice quality basic items and fun cheaper mix in items. Also, I find that I often have a skirt I love, but no appropriate top to go with it. Or a top I love, but only black pants for it.

Any suggestions on an iPhone app or other way to handle this?