If he's whining about having to "dress up", let him where his Levi's 511 Black Stretch Skinny jeans! They look great with a tee shirt or a button up! These Levi's 511 skinny jeans for boys are a cotton/elastane blend for comfortable stretch and have a classic 5-pocket design. So comb his hair over, put him in those uncomfortable shoes, but at least let him where his Levi's!