Well, shit. It's halfway through October, and I just now saw your reply.
Here goes, FWIW:
1st Place (because fat Sims look better than skinny ones anyway):
Look! A pretty new top for my teenage sims.
But...
Being fat is a Very Bad Thing.
This top is a default replacement. HystericalParoxysm's replacement mesh: not as advertised.
2nd Place (truly the worst, but it's Peggy and I believe she's retired from the placement):
I remember one hair of Peggy's which had a gap so huge that sim's head almost disappeared when you looked from backview. It was pay, of course.
Original pic:
The gap:
3rd Place (because Sims shouldn't be able to jut around like snakes):
And Honorable Mention (because it's just weird):
ETA:
There. Onto October!