as everyone had already said, this question's been asked probably since 30 years ago. i doubt there's a definitive and universal answer, since it will differ from person to person.
I like how both styles look, but I can only go Baggy myself. I'm a pretty short/heavy guy (5'6 & 175lbs), so going skinny makes no sense at all for me.
It actually took me a while to figure out what works best for me. When I first got into boarding my buddies were telling me that going loose/baggy is the only way to go. I went with large jackets and pants, and to be honest I looked like a giant toddler for a long time cuz I was pretty short.
After that I figured that I'd give tight fitting gear a try, only to find that tight gear make me look pretty damn fat... So now I'm going with gear that's just about the right size, maybe slightly bigger.