The Trouble of Packing

I'm not complaining about having the luxury of being able to travel, but with the rising airline prices, it is becoming quite a production to pack everything needed to live in a hotel for multiple nights. Fortunately, a member of our party is driving up to Oregon, when we fly and has offered to take a suitcase in the car with him. However, mine, being much smaller than most, barely fits necessary cosmetics (unable to be carried on a plane) and my shoes, let alone clothes for ten days. To solve this issue, I have filled my 'official' carryon bag, and filled it with sweaters, shorts, pants, and dresses. Along with my oversized purse (also filled to the brim with clothes) I have managed to fit everything in.
Being the person I am, clothes play a major role in my day to day life, so naturally, I always overpack. I have four pairs of pants when only one day is forecasted to be under 75 degrees, unnecessary jackets and more pairs of socks than days I'm gone. But what's the damage, if I don't have to pay for a checked bag?!
Have a great week.