I read somehwere once that it's good to let kids choose things. It gives them a sense of independence. Sounds good to me. So in the morning when I get dressed, I like to get my son involved in picking out my clothes sometimes.
I'll put together an outfit and find two ties that match, then let him choose one for me. He gets so excited. It's a fun little thing to do before rushing out of the house for work. Plus, it gets my son used to the idea that grown men dress differently than toddlers, and that it can be fun to pick out nice looking clothes.
In all these menswear blogs I read, people bemoan the fact that a whole generation of men is running around with no idea how to dress like grown-ups. Maybe by doing things like this, we can help a new generation of men to outgrow the "eternal teenager syndrome".
p.s. he chose the new red tie with whale weathervanes on it, by Brooks Brothers. He has a knack for knowing which one I really want to wear on a given day.