We all know it's going to be
BROWN IS FOR FARMER
How about sock garter challenge? I think that's a reasonable proxy for actually doing a no pants challenge.
The Empty Chest Challenge (no pocket square)
Learn for the Masters (TTO's challenge idea)
#Menswear Blog Challenge (pull an idea from a well known blog, like PTO, and execute it. The bonus here, Stitchy, is that you could probably get PTO to cover it :P )
The Prop Challenge (because fuck yeah!)