I like to wear shorts when I walk in the Summer, but for me, Summer ends in early November after the first serious snow accumulates on the ground. It's not the temperatures that motivate me to give up my shorts, it's the snow getting into my shoes. And it's not really the snow that's the problem, it's the mixture of road salt and snow that turns to slop I hate. I won't mention struggling to untie ice-encrusted laces.
Having said this, when I put my shorts away for the Winter, they stay put away until Spring. I have no desire to face February in shorts, even if the roads are bare.
Unlike the people in the article you shared, I don't see shorts as acceptable when others are expecting more traditional choices. I see it as a question of courtesy. I've outgrown the desire to "shock" or "rebel" decades ago and I'm sure the 20 somethings in the article will mature in time as well.
Still, it feels good to know that others enjoy an extended shorts wearing season too.
Cheers, PW.
P.S. This Summer, I had to wear my Winter parka a few times. I probably looked equally silly!