Our expert says:
At various stages in growing up, kids test boundaries and try to express their independence in ways that parents usually find distressing.
First of all, do you have to Dress him, in the sense of putting his clothes on, or can he do this himself. If he can, then part of the matter can be emphasizin how clever he is to be able to put on his clothes so well.
Then comes the matter of choosing outfits. If possible, it's wise not to force one on him if he resists, but maybe put out 2 or 3 suitable outfits, and ASK him to choose which one he prefers. And maybe he'd prefer the top of this outfit with the bottom of that one - this way he's being independent and making choices, but from pre-selected suitable options.
You don't make it quite clear what actuially troubles you about his choice of outfits. If he's like the kid in the advert who insists on wearing a ballet tutu and swimming flippers, well that's an odd choice - but I'd let him make it. An hour or two of being laughed at by the other kids, and the discomfort of walking rather than swimming in the flippers, and he'd be eager to change - so I'd focus on making it easy for him to change his mind without losing face, and switch to a better alternative.
If its a matter of not wanting a jersey despite the cold weather, I'd let him go out and get cold by not wearing one, but ask him to carry a spare jersey in a packet, just in case he changes his mind.
And maybe talk about HOW he wants to choose is it comfort, or style, or warmth, or colour ?
There are many ways in which an ingenious adult can avoid conflict, allow a kid apparently free choice, while controlling the options so none would be disasterous.
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