OH MY GOODNESS.......CAN I RELATE TO THAT!!! My son Tyler has the same issues and I have tried letting him pick his clothes out and like you said he will only wear them a couple of times. He is sooooo particular about his clothing and it is good to hear I am not alone because even though it is a minor issue, it really takes a toll on you when trying to get out the door for school or church. Tyler will have full on 'meltdowns' about it. I would love to know if there are better shoes because Tyler will wear nothing but crocs and in the winter it is a bit cold. Thanks for mentioning this!