I'm going through the same every couple of years. Kind of updating my basic outfit, because the old one bores me.
I used to wear regular-fitted pants and jeans and still do at work and whenever I feel like it.
Recently bought a couple of baggy pants because I realized I had some shoes I couldn't wear with slimmer fits (Accel OGs, Ipath Cats and some bulky DCs). Kinda love how comfortable they are and how I can just forget about them when I skate (no pulling the crotch up before ollieing and such).
I still feel a little like I'm impersonating a teenager, though, but still like how I look.