I hear ya Baron...one of my coworkers always comments I'm wearing PJs when I wear these, so there's some consistency in thought. this is actually the first time I tried a tshirt with these (usually wear a polo or dress shirt)
I love the plaid pants you wear, mostly because I could never pull shit like that off and because I'm a sucker for plaids, argyles, etc anything Scotty. I do think those pants call for a top with a collar though, like a light coloured OCBD. The sweater needs more contrast with the pants so they don't get the PJ look, like a white, or cream coloured top. The brown sweater and green pants looks too samey IMO.