I broke in my grey jersey flap yesterday. In it was:
silver DNKY wallet
silver clinque makeup bag (not much in it: lipstick, gloss, eyeliner, concealer, chanel mascara, lipbalm and a little tester bottle of chanel no. 22 they gave me at Bergdorf's in NY)
phone (nokia e61)
mp3 player (creative zen 16gb)
fine-toothed comb
My keys were in my jacket pocket, and that's all I wake with me most of the time, really-- keys, wallet, phone, comb and if I have room, a little makeup. I love big bags but I don't put too much in them because I walk everywhere, and I hate lugging stuff around unless I really need it! For college, I also take my laptop and some pens, but that's about it.