I am not entirely sure if this goes here, in Talk Amongst, GD, or unschooling. LOL!  Here goes:
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My kids are 17 and 19, so this isn't so much about them in the present as much as it is about how I parented when they were wee. It's also about other kids in my life that are still young yet.
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My approach: if it's cold/wet/otherwise wonky weather I may make mention of such to a child when we are preparing to go outside or leave for awhile. I might say "Hey, it's kind of wet and cold outside. You may want to grab a coat/hat/scarf/etc." or that it's supposed to get cold and wet and that I'd hate for them to be uncomfortable unnecessarily later on should they not have it. I may mention that we can toss it in the trunk or a backpack, etc. In other words, it's never an order or a big huge deal.
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So, what if they choose not to bring jackets and etc and are cold later? Well, in some cases I have grabbed the stuff anyway thinking ahead, and in some cases I haven't. And they were cold. It was never a pre planned "lesson teaching", but if it happened we talked about the obvious, I tried to warm them up and we moved on. In the future, should the same situation arise, I might say "So hey, remember that time we didn't take the coat and really sucked? Yeah.. might want to grab it." Again, no drama, no arguing, no told you so, no punishments. To me, this kind of discussion is so super invaluable.
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 Why do parents/adults and kids fight about this!? At a ritual recently I witnessed a total meltdown between parent and child over this. It was about 48 degrees or so, very light rain and child (about 7) didn't want to put the mittens and scarf on. They were already wearing a hoodie. What followed was parental cajoling, threatening, yelling, sadness, and so on. Now, I surely don't mean to judge this parent that I don't even know. The Gods know I've had my moments of awfulness, mostly in public, and I couldn't explain those now if I tried. I don't mean to sound nasty at all. and I am fully aware that any number of other things could have been at work there. That being said, I couldn't help but silently go through that situation as I would have w my kids and felt badly they weren't able to reach that place right then....
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 So we have a young friend who visits us. Home is a hard place right now, and we like being a good place to be. He is 10.5 yrs old. We live in the Pac NW, and it rains from Oct to April here on a regular basis, and is rather chilly for much of that. I have handled the coat thing with young friend the same way I did with my own kids. AKA: Here is the situation that is or may develop in the near future, here are the tools and how you might use them, and please feel free to ask me any questions or for help along the way should you need it. :) So young friend and I on a strange kinda warm day (58 degrees ha!) were standing out in the rain with the dogs for a few minutes. It was a freakish 5 minute hard down pour, and it was awesome. My partner's parents (we are staying on their property atm) freaked about him not having a coat and hat on. I was thinking, "I'll go alert the freaking media..." Also, I don't see a little rain or a short amount of time spent outside in chilly or windy weather without a coat as the end of the world. Clearly, if a child is uncomfortable or in an unhealthy/dangerous situation we do what we reasonably can, but I've never heard of a disaster from a child being wet from rain. Who wants to live in a world without rain falling on you anyway? 
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If a child knows what is up, and knows what to do if he is cold, in pain, etc... what's the issue?
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 from other adults when they see him out playing.Â