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Easy solution, get your son to choose his own clothing. Then you quickly go from, "How could you have picked that for him?" to "How cute!"

Plus your son will probably enjoy having that piece of control.

Do you also buy the clothes? Being involved from the buying point helps a lot to understand the logic of it all IMO. I had the same pb with the different baby creams, and had to choose one in the shop to really get what is used for what.

Eh, don't feel bad. If they're not denim or button down there's really no difference in kids' day-clothes vs. their pajamas. "Convention over configuration" I think we tend to call it in our industry :).