I have three theories about Drew:

1. Somebody full on lied to him and convinced him he has great fashion sense and so he is as much a victim as the rest of us.

2. He hates me personally and wants me to look like an idiot.

3. He's bored and finds the fashion-pedestal we've placed him on amusing, and wants to see whether or not we'll put on ridiculous outfits just because he tells us to.