I used to be like that. I had a different pair of sandals and handbag for every outfit but having been back 17 times I have learned. If I do take books they are in my hand luggage. Apart from toothpaste, brushes etc. We buy all the sun products, shampoo etc in the resort. Its more or less the same price as the UK. Saves from having to pack them. As for outfits I confess I am guilty of taking too many. Coming home with things I haven't even worn. Something along the lines of "it looked alright when I tried it on a home but it looks horrible, I've got nothing to wear now"
I now have my 'travel clothes' these are my trusty outfits that I feel comfortable in and take every year with the odd new outfit just so that all the photographs dont look the same! I only take three pairs of sandals and handbags, only two of which I wore this year.
We have been lucky so far, only once were we over and they let us through, and for some reason David instinctively knows when we are over as he has to carry the cases!