Help, my son is a picky dresser!

Tip 1 - Tell him how "this shirt would look better on him"

Sometimes kids need that extra boost, you need to show some excitement "wow, look at this shirt, this shirt would look so much better on you... or should I give it to ... (insert his friends name)" this usually works like a charm for me.

Tip 2 - Let him think he has a choice

The best way to deal with this is to get shirts for your son yourself, like, at least 4 shirts and show him two at a time and ask him which one he wants to wear to school and which one he wants to wear at home. Have him choose two shirts for school (out of the 4 YOU selected) and two for home. This way he will think he has chosen them and will be willing to wear them.

Tip 3 - Tell him to pick a shirt the night before

Instead of having to fight in the morning everyday, ask your son to pick a shirt the night before school so that he has no issues with it in the morning. Just put out 3 shirts in front of him at night and ask him to choose.

Tip 4 - Tell him his favorite shirt will wear off sooner if he uses it everyday

Since he wants to wear his favorite shirt everyday, you can tell him that using it like that will wear it out sooner. If he really wants to keep wearing it he will be more particular about it and won't insist that you give it to him everyday.