Randomize Outfit: YES! I would love the option to randomly create mixes of things! Both from what I own, what I don't, or a combination (so 3 different options)
Searching: it's clear that things are tagged, so I too wish we could more easily search for items within our wardrobe
My suggestion for Wardrobe is to get rid of the little wooden cabinate, and to put purchased clothing at the TOP of each clothing 'store' page, with a different background or maybe a border to show that you already own it.