My 5 year old son refuses to wear underwear. Should I make him?

Captain No-Underpants


Dear Funny Problems

My five year old son will not wear underwear.  We’ve tried every kind – boxers, tighty whities, the hybrid kind. He won’t do it.  Is this a fight worth fighting?



Dear Holly

Sorry to be a square, but underpants have been part of the dress code since we got banished from the Garden of Eden.  When he’s an adult he can make the decision of whether or not to go commando, but for now the wee man needs some underoos.  Life is all about give and take and nobody (children included) likes to be forced into doing anything. If force is involved it will continue to cause conflict, this has to be a decision that he feels like he is making on his own.  He has to want to wear the underwear and it’s up to you to get him excited about it. You can’t use adult logic to persuade a five year old, it’s a language they don’t speak. Kids need fun-size incentives and who better to ask than Captain No-Underpants himself.    

For every couple of days that your son successfully wears underwear offer him some token of appreciation.  NOT a toy, kids have too much junk as is. Perhaps you can let him pick dessert or a movie for the family to watch.  A cute idea might even be to bake a cake in the shape of underwear and throw him a little party after he has achieved some success.

If you make that cake please send in a picture because I think it’s the best idea I’ve ever had.



1 thought on “My 5 year old son refuses to wear underwear. Should I make him?

  1. Dear Holly and FP: I have raised a number of children and I find the fastest solution to ANY problem dealing with having children comply is reverse psychology! I unlocked the secret to potty training when I told my 4th child: “Do NOT go into the bathroom and whatever you do…do NOT sit on the white seat in there. Voila! Instant non-compliance and total success with the tinkling sounds hitting the enamel. Prohibit your child from wearing any undergarments. Make it a point to collect all such garments from his reach. Think of the benefits, less folding for you and a very real possibility that this stage will be short lived when he begs you for underwear. The only draw back is that in the meantime, you can’t relay the age old Mother mantra of: “Make sure you have on clean underwear in case you are involved in an accident and have to go to the Emergency Room”!

    Good Luck,

    Mamma J


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