Now despite his coolness, or maybe because of it, he's kind of a picky dude. So shopping for him, though I sparingly do it, is kind of difficult. However, I stumbled upon this Pendelton X Opening Ceremony collection that has a few pieces that look like they may push him stylistically without going over board.
source Rotten Fresh
He's always talking about getting a white blazer, so the white jacket at the top seemed like a combo of dressed up white with dressed down plaid lining. The second jacket is just fucking awesome because it turns into a back pack-ish type thing for when it gets too warm. And the third plaid shirt has a hood. Hooded tops are always preferable to hoodless tops, he and I see eye to eye on this saratorial ideology.
I gotta say, its kinda fun flipping the script and shopping for menswear instead of women's, the added challenge of the items not being for me make it a nice change of pace.