I made a dock for my iPhone out of Legos and I'm highly considering doing it for my watch, always been a Legos fan (never too old for them) and I think it would look cool!
I played around with the SS box, trying the separate the the piece to which the suede is attached from the outer piece. I could move the edges a bit, but the bottom must be glued down really well.
If I could separate that piece, it would just take drilling a few carefully-sized holes into the plastic.
To go all-out, I could rig some adaptor to go from the male end of the watch charger cord to a female lightning port.