Originally Posted by
robatsu
Sure, read about it
here, boxers, shorts were some sort of stout fabric, pulling my kid in a trailer, as well. Worked ok for me, don't think it was some big tough guy thing. Boat shoes, as well, for complete dorkiness.
From your linked text:
"The morning, very early morning, of the event, my son and I saddled up on the Gran Tourer and trailer and headed out for Leesburg,
about a 42 mile journey...."
Not quite a century.
I get that it was a round trip effort, but you were off the bike for a long period of time in between the first half and the second half, no? That helps a great deal with the cumulative effects of the constant chafing.
I used to do long rides in street clothes, sometimes without too much discomfort at the end, and sometimes not. But with cycling shorts - no seams, no chafing. It was worlds better for me, so I never looked back.
That being said - I did a pretty arduous century last year on the east side of the Sierra, and midway through I was passed by a couple of young men wearing nothing but board shorts and flip-flops. They were having a grand time, and didn't seem to be suffering any ill effects for the short time I saw them.