Dressing Your Pet for Halloween?

Okay, I'm on the fence with this decision. I have a small Yorkie who is my baby, should I dress him up for Halloween? I mean I've seen some dogs in some insanely hilarious halloween costumes, but the dogs always look severely depressed. It just seems wrong.

He likes wearing shirts (mostly because he thinks he's about to go outside), so maybe I'll just let him wear his Chicago Bears Jersey? Good enough?