Boy do I need this thread! I will have to pack 2 weeks worth of clothes very soon. We're having our apartment rennovated and can't move in til we get back, so we'll be in a hotel for 2 nights before we leave and 1 after. I want to pack now but we don't leave here for another 9 days!
I always try to wear my disney clothes on my trip. I will wear khaki shorts and a disney shirt most days. I bring many, many extra socks and extra shoes. I make sure to pack my pooh overalls for one day, 2 bathing suits, several nice outfits for dinners (and SO's suit for V&As), 3 pairs of sandals, outfits for going to pleasure island, etc.
It's a good thing we're driving. I could never check all my luggage. I do weird things like pack my shoes in shoeboxes so they can't get crushed. Rolling clothes does help some to have them take up less room. I think we're actually going to have to go to TJ Maxx and buy my SO some new T-shirts for the trip. He doesn't have enough, since he never wears them in real life. Extra socks too.
My most important thing to pack? Coppertone waterbabies spf 45 - 2 bottles, I will go through them in 2 weeks. Last year I didn't even get a little sunburned by using this stuff, and I'm so pale I glow in the dark! I slather it on twice a day like there's no tomorrow.