I wear a different color shirt everyday, all large tshirts, most with the chest pocket. No name brand clothing, nothing with a logo sticking out, i don't buy anything from aeropostale, american eagle, etc. All my tees are from offline, goodwill, or a nicer clothing company such as Land's End.
Rock the khakis, regular tan to darker for nicer outfits. All mostly hand me downs from my brothers, with nicer pants i get at TJ Maxx. Fresh courds in the winter, with some plaid shorts or cargo shorts when it's nicer out, although i tend to prefer pants over shorts.
Throw on a nice looking sweater, some flannel, or a dope sweatshirt for the cooler temperatures. Other than that, the only time i will wear "nice" clothing, i.e. a button down shirt, tie, suit, nice pants/shoes, nice polo, is when i'm out to dinner on a date or something. I figure i shouldn't dress up to impress if the rest of the time i'm wearing my regular average clothes.