When you observe certain subcultures. Take the hipsters (current style is a mixture of skate & urban wear aka street wear) and the yuppies (east coast influence).
I've seen this in LA - beanie + flannel (or sweater) - when it's 65+ degrees, then people dressed, when it's below 20' with no hat and heels in both Chicago and NYC.
Why?
Personally my own style is a mixture of what is called hipster and yuppie, maybe even prep, then add in a dash of "classical" men's wear, but I sure as heck wear the appropriate clothing dictated by the weather. If I find myself outside in warm weather for a certain duration I'll probably wear a baseball cap and either a button-down oxford, a t-shirt or polo. If it's cold outside I'll be definitely wearing a wool hat, gloves, a heavy coat and some sort of boot. When I go swimming I'll wear swimming trunks. If I do any type of athletic I'll wear athletic shorts and an athletic t-shirt, sports glasses and the gym/basketball shoes.
And when I take a shower I take all my clothes off.
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