well your thread title says "tell me what you think" so im going to tell you exactly whats on my mind..
You have taking the level of "baggy" clothing way to far.  Cmon, like I wear baggy pants and jackets, hell even i have a saga t that is just above my knees.  but what your doing, i would consider overkill.  Seriously, if i saw you walking around the lodge like that or skiing on my local mountain i would instantly think either...
a. douchebag
or
b. kid who cares way much more about what he looks like then his actually skiing..
but bottom line, its your money ( i hope it is), you do what you want with it.