Before I take a trip I draw what I'm going to pack so I don't forget anything. I like to pick a color scheme (black, white, gray, blue) and mix thing up (textures and shapes) so it doesn't look like I'm wearing the same thing every day. I went back east to help my mom unpack but we also went to a financial worship (I know all these secrets about your FICO score now) and had a meeting so I had to dress up a bit one day.
My datebook is thick but palm size (4x6ish) and has the cutest dog illustrations in it. If I don't have anything written on the pages I use them for notes, doodles or mini collages. The back of the book has 40 or so blank lined pages that I use for writing and I have ripped out quite a few to leave notes for people and plenty of the pages are left. The girl with the red hair is one of my bookmarks.
The weather went from hot and raining to cool and sunny so I didn't end up wearing my skort or short skirt but they pack well so I didn't care. I fold everything with a board to make them super flat and roll the skirts and workout pants. I board fold my t-shirts at home because I have an old fashioned dresser with shallow drawers and you can get so many more stacks in t-shirts inside of it. I have an actual folding board but you can easily use the cardboard that comes with 81/2 x 11 packs of paper.
I have all of my clothing memorized (makes shopping so much easier) so I make my list while I'm out then I just come back and make sure nothing is in the laundry. When you stick to the same colors you can usually stick everything in the same load of laundry (the purple dress I use as a night shirt). I always wear jeans more than once and pack extra underwear in case I workout that day and need a fresh change of clothes for the evening. Wear your heaviest shoes on the plane and in my case those are clogs that give great foot support and easily pass for dressy.