I am very much a person who appreciates perennial things. Things like a Lacoste shirt, a Clarks desert boot, Persol sunglasses and Vans shoes that have been the same forever. There are certain things that once you find it, you like it and it's done. I like Italian clothing, like suits from Battistoni and I have a shirt by Piero Albertelli.
The more you travel, the better you get at it. It sounds silly, but with experience you learn how to pack the right way. I remember one of my first trips abroad, travelling around Europe by rail, fresh out of high school. I brought all these books with me and a paint set. I really had too much stuff, so I've learnt to be more economical.