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If you know the weather will change later, or you have a certain function to attend, or your child will need to have a certain kind of shoe to participate (sneakers vs. sandals, for instance), you need to insist that your child do what is appropriate — that he obey you.
You are the one with the knowledge and experience of how conditions can change. You are the one who knows what form of dress is required for which occasion.
For some reason, dressing appropriately (to the weather or activity) is a point of capitulation for a lot of parents, especially mothers. Consequently, we have a lot of overheated or shivering children out there… and many who know they are not dressed appropriately, but don’t know what to do about it.
Without creating a power struggle, you need to insist that the proper thing be worn or brought along. This is an art for mothers to learn! Use your common sense — perhaps the sweatshirt or tights can just be put in the car or taken off later or what have you.
If it truly doesn’t matter, let it go. Very often, though, it does matter to their — and your — enjoyment or sense of decorum (depending) later on.
But if you want your child to learn to obey in all things and thus, paradoxically, to learn self-control, this is one area you should not readily relinquish. I’m not sure why the prevailing notion is not to help our children in this regard.
For all the details on this subject as well as all the reasons not to insist and my answers to them, go here and here. [These links are about dressing for colder weather but the principles are the same.]
I will remind you of all this after summer, don’t worry. But even in summer, there are times the whole outing will be thrown off if the child won’t bring a sweater or refuses to have the right footwear.
And then later, when he’s older, you will want him to be in the habit of taking your warnings seriously in other situations; if he has the habit of trusting you and obeying, he will.
As with everything here at the SFH, the best thing is for you to take my ideas, which come from my experience of escaping feminism to enjoy the gift of 45 years of marriage, seven children, and more than a score of grandchildren, and apply them to your situation with discernment, prudence, and confidence — and a sense of humor!
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For the longer version:
My book on how to live with the Liturgical Year: The Little Oratory
Good advice. It's too much for a child to have to make all his own decisions. I think it gives the child a sense of being unprotected, a sense of parental unconcern.