I have a few basic pairs of khakis for work, and a couple of similar yet different colored dress shirts for work. I hate ties, but I'm required, and I've narrowed it down to two or three that match the shirts. On my time, I wear the same thing: shorts and t-shirt. Because I do hate dirty laundry, I usually multiples of the same shirts, just in different colors so people don't think I'm dirty. If I had my way, it'd be shorts and t shirts all the time (like when I worked at Borders or Tower Records, the good old days.)
But sometimes I get frustrated because I see a shirt or something that I like on other people, and will risk buying it, only it will bug me to death, either the feel, the heaviness, or some kind of pattern that will distract me all day. ( I tend to go with solid colors nowadays, though I do like a sporty shirt with stripes on the sleeves.) But it always comes down to a simple t shirt and shorts, or in the winter, a favorite sweater, not too thick, not too heavy, but just the right softness and warmth level without sufffocating.