I am a mother of 4 boys. Ages 6, 4, 2, and 11 months. In the summer, I have a big fancy basket that has swim trunks. They wake up, pick out a pair of shorts and go play outside. It looks more appropriate, like they have been swimming (which we do) And forget shoes! But the moment my two older boys go to a friends house or we need to jump in the car to go somewhere, I simply say..."Lets be RESPECTFUL, so slap a shirt and shoes on, and lets go!" They have gotten used to it and when I say lets go, they usually automatically grab their shirt and flip flops or whatever. When kids are home, they want to be comfortable and free. They would live in underware if they could. My townhouse back porch, faces a playground/courtyard for years, Ive seen it all! And nice trunks look classier, like happy active sporty yuppie kids. Than the boys who roam around everywhere in regular shorts only. Dont ask me why. Its like a nice looking person with a unibrow...its all in the details. Or seeing a classy hot babe smile, only to reveal brown snaggle-teeth.
In the winter I dont see you having this problem, let them live in their underwear at home until they are around school age. When its cold, I slap comfortable "regular shorts" on my 6 and 4 year old. And if we go somewhere, they change. If they visit someone, they have to keep their clothes on, like respecful gentlemen. They are Ok with it because they get their "fix" of being comfortable at home. You know, the old school thing is to always wear a shirt around the ladies. I think that is admirable and sweet. But boys need to be boys (leaders/role models) also. And cannot be stifled into wienies.

Know how you feel! My boy are the only ones on our road who do this! Even when I check they have shoes on when they leave the house if I check on them a few minutes later they have often 'lost' them again! But in the scheme of things it's not really a big deal, is it? Also, I once spoke to a farmer whose kids wandered around the farmyard with no shoes and she was convinced that it's very good for the immune system to go without shoes!

With your boys, what sort of places do they go around like that in?

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Know how you feel! My boy are the only ones on our road who do this! Even when I check they have shoes on when they leave the house if I check on them a few minutes later they have often 'lost' them again! But in the scheme of things it's not really a big deal, is it? Also, I once spoke to a farmer whose kids wandered around the farmyard with no shoes and she was convinced that it's very good for the immune system to go without shoes!