I typically wear business casual at work. Although the shirt I have on now looks kind of nerdy as it's got your squares on it, I find it to be quite handy. What if you cannot measure something as you do not have a measuring utensil with you? No Problem! I can just simply put my arm up to it and be like "it's 5 shirt squares!" Quite efficient!
At home, I typically walk around with a bit less on .
When I'm out, I wear whatever I wore to work except with the shirt untucked.
When I'm out but never dressed for work (i.e. weekends), I wear Hawaiian shirts with a undershirt and some nice cargo pants. It might be considered scrubby, but I'm quite comfortable in them, and hey... at least they're not the cheap Wal-Mart $5 Hawaiian shirts... no sir, I overpaid for mine at JC Penny!