I tend to get creative with the whole carry-on and personal item.
I always wear my leather jacket which has some decently sized pockets. This is where I've usually stuffed:
Sunglasses
Nintendo DS
Headphones
Cell phone
All paperwork for flights/travel
Notably, I always have a fuzzy neck pillow, which is usually crooked over a strap of my laptop case.
In my actual carry-on bag I tend to stuff as many outfits as possible and some basic approved toiletries. My camera goes in as well if I bring it. If it is winter my carry-on can get a bit bloated with scarves, gloves, ear muffs - as none of these are needed in FL ever during the winter but become an immediate need once in Chicago.