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Thank-you Buenchico. As he is only ten he doesn't really play out much with other kids. The furthest he gets is in the garden with his brother. For this I usually dress him in clothes like shorts or if it's cold, jogging bottoms.
I just like him to look smart although he doesn't seem to like this. When he comes in from school, I lay his clothes out for him which usually consist of slacks and a shirt, maybe with a plain t-shirt underneath if it's cold.
I know if I trust him to choose his own clothes we will end up with a wardrobe full of skull and skateboard motifs.