Wow! You’d have been judgmental of at least 20-30% of men in that age group who were dressed that way at the Art Institute and surrounding parks and streets. Some were wearing button up short-sleeved shirts, and some Tevas or Birks instead of athletic shoes. But I’m not sure exactly how else a mature male is expected to dress to do casual leisure activities when the temps are in the high 80s.
Seersucker suit, espadrilles, a panama hat and shades.
Leon had that down.
Nailed it!
There! How hard was that?!
Love Leon I do, kayaker.
Very actually. When you live on a dirt road where the weather is brutal, Leon’s outfit would not make much sense.
What one wears in one’s own home is not a matter for others to judge. But even my prairie farmer grandparents had “going to town clothes.” I think Ulfrieda has put the case admirably.
If you want to see me in something other than jeans, a Hawaiian shirt and “running” shoes, you’re going to have to take a shower with me. I’ve gotten rid of everything else. Classroom, dinner, concert, funeral, wedding…I just adjust the tone of the shirt to match.
O the humanity!
Pretty much, yeah. 
Some of them can get rather…bright.
He was unique! I got to meet him twice. Once after a show very early in his career, then once after he had stopped performing and lived not far from me. When I heard he was not doing well I wrote a note offering help if he needed it. His wife read my card and replied, thanking me. He died a short time later. He was 127 years old (according to his biography, to which he always remained true)
Now THAT would catch my attention!
I remember one time some years back I was doing an arbitration, and one of the lawyers (in Chicago) appeared dressed like that. But I think he had a boater instead of a panama. It really made an impression on me. Why this guy decided that, instead of wearing a conservatove suit like 99% of the other lawyers, or maybe even wearing a flashy, stylish suit, he decided the impression he wanted to convey was that of a southern gentleman lawyer of some generations past… (Didn’t help any that he was completely incompetent!)
A couple of years back, one of my nephews got married in 100-degree Texas heat. The husband of one of my nieces bought a seersucker suit at a thrift store, trimmed the pants to shorts, wore the vest, cut the sleeves off a white dress shirt, and used some of the left over seersucker to make a bow tie. Was QUITE the ensemble! 
I suppose it matters greatly where you live. Around here (South Florida) wearing long pants in summer time makes you stand out as unusual. Or as somebody who’s dressed for work.
There are certain cultures, often in hot climates, where things like shorts are frowned upon as the stigmata of youth. Although many of these cultures do value fashion, it’s a bit impractical and outdated given modern sensibilities and swelter. People do judge you for what you wear. I enjoy bright colours but used to get the odd comment from the men-who-always-wear-black-or-beige. Who cares?
I’ve heard that linen (flax) is better than seersucker (cotton) in hot climates. It wrinkles like nobody’s (dirty) business and has to be ironed. That and the cost are why I now wear cotton, but I used to enjoy wearing linen.
Yeah, I guess that makes some sense. But shorts are pretty ubiquitous most places I look in the US that are not terribly formal.
I always thought it a refreshing look when you’d see professionals in Latin America wearing short-sleeved shirts. As opposed to the idiot “professionals” in the US, who wore wool suits and ties no mater how hot the weather.
I am also curious what judgement you’d pass?
There goes someone who likes to be comfortable?
Absolutely. “Insouciant chap” might be another; in extreme cases, “callous disregard for the humble sensibilities of others.” “Maybe I should spot him a $20” is also possible, as is “Don’t make eye contact and edge to the door.”
I think the thread has indicated just about everybody judges, or is at least sensitive to, the vibes people give off with their clothing decisions. Ulfrieda has put it nicely.
I should add that as I was looking for my cravat and knotted cufflinks in preparation for an outing to the hotdog cart this afternoon, my partner pointed out I was wearing a torn “I’d Rather Be Smashing the State” t-shirt, over the knee-length “shorts” (I call them cargo culottes) and socks that said “Fuck this Shit.” Judge not lest thee be judged.
I dress so I don’t stand out too much at Kroger.
Usually this involves wearing a shirt and shoes. Shaving every few years is optional.*
*we live in a town that might be called the Gateway to Eastern Kentucky. Quite a few mountain men with long white beards, wearing overalls. The women are of similar appearance, though beards are typically shorter.