Always loose trousers with several pockets and a soft stretchy shirt. If flying, walking shoes (heaviest part of luggage)and fleece tucked through handle of carry-on bag.
If driving, same top and trousers but softer shoes and just chuck everything else I might need in the back of the car. If cruising, compromise. Same as when flying but I think more about what I will REALLY wear. Put it all out on the bed, hang at least half of it up again and pack the rest. I'll probably get it wrong and still bring several things back unworn but never mind, at least I feel as if I made the effort.
What I would love to do is travel looking chic in a dress. I do envy those who can. I have a couple of so-called "travel dresses" but they seem to need much ironing which is never my favourite activity and certainly not on holiday. So I guess I'm stuck with my trousers and shirt.