It can be more complicated than that. The next shirt in line is on the ironing board, not in the closet. I have to wear a tie today! I'm pulling a shirt from down the line. Can I also have a reminder of which pants go best with that shirt? I didn't do laundry yet so half my pants aren't available. Now I did do laundry, so half my pants have only one wear left in them and half have two.
Maybe you're overcomplicating it? Pulling the next shirt in line is a suggestion, not a requirement. Maybe you want the second or third shirt in the queue. A small amount of common sense is required, but less than if you were looking at your entire wardrobe at once with no other information about it, and trying to make a decision.
I just wear the same thing thing each day, or close enough. Being married Middle Aged male Dev nobody cares as long as I don't smell and I'm reasonably neat. I certainly don't care, nobody to impress.
Having five sets of the same clothes certainly makes life easier. And when I finally do change my attire the office gets a laugh out of the fact I actually went into a clothes shop.
Here's a <a href="http://i.imgur.com/VNJ08Ra.png">screenshot</a> of the thing I made in Flask to keep track. Orange needs to be washed next time I wear it, red needs to be washed now.