My go-to pants during the fall season is always some kind of denim. Because the fall/winter months call for lazy outfits on the norm, these pants provide depth and dimension all on their own. Paired with a slouchy sweater, oxford shirt or a bodysuit, it can transform what you might still consider a lazy outfit into a trendy look.
As for the bag, I have no words. All of my Japanese fairy dreams have come true with this cult classic (only $88!)