In my younger years, I rarely wore shorts. It was pants, even if the weather reached 100°F, which was quite often in deep South Texas, aka the Rio Grande Valley.
I think it was a cultural thing for men in the Rio Grande Valley to not wear shorts. I don't recall seeing many doing so. I think it's because shorts were meant for women. Not men.
So, if you knew me back then, you'd see me wearing either dark jeans or dark slacks during the hot summer days--364 days in a valley's year.
It wasn't until I met my wife that I learned to wear shorts. Really. I think there was a day during the hot Central Texas summer where she inquired as to why I was wearing black slacks. I didn't have shorts to wear outside the apartment, and I guess we clashed--her in light color shorts, me in dark pants.
The only pair of shorts I could wear, I wouldn't dare. They were short cut off jeans that were passed on to me by a friend of mine who didn't have to worry about not looking good in them. Me wearing them, however, would definitely give people the wrong idea.
Now, it's a different story. I'm in shorts and t-shirts when I am not at work. It doesn't matter if there is a chill in the air. Shorts are my style.