All good information, but I guess I would have started with a few basic questions ... some of which have been mention and some are very obvious.

1) time of year
2) length of trip
3) trip style (daily move to base camped)
4) portage style (single to as many as it takes)

I put time of year as the initial question because to me it has more impact on how I pack than most anything else.  Since I frequently travel in early spring (e.g., mid-May), I carry substantially more clothing than for a late summer trip.  For early season travel, I don't take any cotton clothing (the only exception might be a bandana, but even some of those are of synthetic material).  There is only one major reason for this, they don't tend to hold water and will dry more quickly that other forms of clothing.  Being wet when its cold (e.g., right after ice-out) would not be my first choice and that is a HUGE reason for taking a "backup" set of clothing, even on a short trip.  Otherwise, you can wear your clothes as long as your trip mates can tolerate you. (However, I find I do sleep better if I'll at least do a rinse--if not a head to toe bath--during a 2-week trip.  I do try to do that on a slack-wind day when the temp's get out of the 40's.)

Along these same lines, I'm likely to take a fleece vest or early season warmth, rather than down.  Wet down takes a long time to dry and doesn't produce the desired effect when wet.

All this said, if I'm traveling mid- to late-summer, much of the synthetic clothing is ditched in favor of more confortable wear (e.g., a fair amount of cotton...especially t-shirts).

Keep in mind, these are personal preference ... but with some reason behind the choices.  Some folks are just find with blue jeans and cotton shirts whenever they trip.  But I'm just a dumb southern boy that takes hypothermia somewhat seriously.  (My "swim" on last year's May trip simply reinforced that a bit.)

dd