I'm a simple fellow, and I prefer simple clothes.
While it's warm out, I favor cargo shorts and converse, finishing up with a T-shirt with a witty/snarky slogan on it and a Hawaiian shirt. Why Hawaiian? Because I like to walk around, and if I'm not wearing my Hawaiian shirts, rude tourist jerkwads have to ruin my day with stupid questions.
Now, when the temperature starts to drop, I prefer a solid shoe over a boot, as well as fleece lined pants. I still use my t-shirt/Hawaiian combo, covered by a thick jacket.

You can tell a lot about a person by the way he's dressed. So, if you see a displeased individual in a Hawaiian shirt, don't ask for directions unless you want to wind up lost. A personal favorite is sending people to Canada.

Next time on TfaBP:
Set Sail!
I, Prophet's favorite Anime!