bag that may or may not get checked, for $$$ since I have no status on any airline, right now a 20-inch hardsided burgundy Hays roller thingie:

clothing
shoes
scissors
extra bag for dirty laundry

carry-on when I'm checking my other bag, a maroon L.L. Bean backpack:

jewelry
mp3 player charger
phone charger
five books
extra shirt
extra socks
extra underwear
pajamas
dry makeup
other toiletries in an easily-removable plastic bag (mascara, shampoo, conditioner, moisturizer, lip gloss, generic Flonase, contact lens solution, sunblock if necessary)
toothbrush
adapters if necessary
travel pillow if necessary
five or so books
camera plus battery charger
doll who's a thicker version of Flat Stanley
razor
earplugs
tissues
contact lenses
normal sunglasses
travel journal
Band-Aids (tm)
a small reuseable bag

purse, whose items might go in the backpack if I'm lucky, thus giving me only two bags:

phone
mp3 player plus slightly broken Shure SE110 sound-isolating headphones
prescription sunglasses
CharlieCard
wallet
brush and face powder
printout of itinerary
passport
extra earplugs
pen and extra paper
tissues
solid-form medication (generic Zyrtec, for instance)
keys