i just have to second the llbean toiletry case. they may not be the sexiest things around, but they are very very functional and come in lots of sizes. i have two.
regarding luggage, i would not pay crazy $ for a name brand, personally. my primary suitcase is really fabulous quality (i travel a lot and have had it for 5-6 years) and i think i paid $150 for it and a carry-on to match (which my husband uses). it's heavy-duty nylon with great wheels.
as a carry-on, i usually use a big custom-made fabric tote. it's light, and i can throw it in the washing machine when i get home. it's all about function when i travel...
but if i had a private jet and someone to carry my bags, well...
