Unfortunately, when everybody else went off and learned this arcane system I was apparently playing Battletech. Now I know that large pulse lasers followed by SRMs (order very much dependent) is generally strong play, and everybody else knows that striped blue and white doesn't go with ... I have no clue what it doesn't go with, but it doesn't go with something. A lot of somethings, apparently.
It shouldn't be that hard to snap a photo of an item in my closet, play "20 questions" to classify it, and put it in a DB. Then every day, when I wake up, the app generates an outfit (I don't know, maybe a genetic algorithm would work for this, it is probably straightforward constraint satisfaction) and tells me "March 25th: Patrick, get these three things out. Can't find one? Click 'Backup Plan'."