I've read most of this thread, and I would get a dress for my (hypothetical) son... if he ASKED.
Pointing to one could indicate a myriad of things, and I would be fine with putting one in the dress-up bin based on pointing. But.... I probably wouldn't wear it out for errands unless he actually asked to do so, with words. Mostly b/c I don't want to be the mom who "forced her boy to wear a dress". I'm more talking from my (hypothetical) son's perspective as a teenager/adult, rather than other people's perception of us. I would like my child to be able to say that he picked it, b/c dresses are a very gendered item in our current culture (even more so than skirts, IMHO). I would have no problem dressing a child of either gender in any color, before they could give their say.
My brother had really long hair as a preteen/teenager, and got mistaken for a girl a lot... but he was cool with it, and really didn't care what others thought. He also wore a kilt for his wedding. He didn't want to wear dresses to the grocery store, though. My mom would have likely let him, if he'd ever asked.
We had a wonderful friend/neighbor as a child who loved sparkles and boas, and he wore them everywhere.... but he asked to do that. He's now a former Olympic figure skater, so I guess it's good he could put up with a sparkle or two.
I would also prefer my daughter not put on her giant tulle dress to go on normal errands either. Fancy dresses are a PITA when pottying or anything else. I also imagine that most dresses are tricky for little boys to potty in if they stand up to pee, coordinating holding everything out of the way...
My two cents. Good luck.