In mouth: Cigarette
Left hand: Starbucks Venti Frappacino
Right hand: Empty urine sample cup for random drug test. You can go around all night asking people to fill it for you so you don't get busted by your parenting coach.
In Purse: Make sure you have a court order that prevents you from visiting your kids.
Car: As you pull up to the party, back into someone's car....but don't tell them. Make sure someone films it to play on TMZ.
On head: Skanky wig. Hell, it could even be on backwards. No one would think anything of it.
On leash: Dog that you will lose interest in within minutes and give to shelter.
Hmmmm.....that's it.
BTW, yeah I totally agree about the hat thing. She is always wearing those hats! Great costume idea. Sooooo many options!