How to Get a Toddler Boy to Want to Wear Underwear

By Cynthia Measom
Underwear is easy for toddlers to pull up and down.
Underwear is easy for toddlers to pull up and down.

Potty training is a unique journey for each child -- some more wrought with trials and tears than others. However, one of the positive steps in each toddler's journey is when he finally reaches the stage where he is developmentally ready to wear underwear instead of diapers or training pants. Even if your son doesn't immediately take to the idea of transitioning to cloth underpants, you'll be able to encourage and motivate him to make this important and exciting change.

Praise your child for his good potty habits and, after several weeks of success, tell him you'd like to take him on a special trip to pick out his very own underwear -- just like grown-ups and older kids wear.

Take your child to a store that offers a variety of designs in his size. You want him to be excited and motivated to choose and wear his own underwear; toddlers usually like being allowed to make their own decisions. Designs vary from depictions of rockets and trucks to favorite cartoon characters and superheroes.

Help your child call relatives and friends to tell them his news about making the leap to underwear status. This little boasting session can serve as a source of positive encouragement for him.

Let your child pick out which pair of underwear he wants to wear each day to encourage a sense of ownership.

Start out with a goal of two hours per day in underwear to minimize accidents.Take your child to the potty and encourage him to relieve himself after the first hour. Be prepared and patient; some toddlers may not go during the potty break, but instead hold it and have an accident a few minutes later. If this occurs, clean him up and put him back in a fresh pair of underwear for the remainder of the two hours.

Change back to a diaper or training pants at the end of the two hours and praise him for his efforts.

Extend the underwear sessions to three hours and so on -- with regular potty breaks -- until your toddler is wearing underwear full-time.


Always be positive, even in the face of accidents. Negativity can cause your child to regress.

When you go to the store to buy underwear, make the trip a celebration of sorts to motivate your little one.


Once your child starts wearing underwear, avoid overalls, belts or pants that are hard to unbutton. The ability to quickly pull down pants and underwear is vital to his potty training success.

Switching your toddler boy to underwear before he's ready is a mistake, according to clinical psychologist Edward Christophersen, writing for The underwear won't contain the waste and only sets him up for failure, disappointment and undue stress.

About the Author

Based in Texas, Cynthia Measom has been writing various parenting, business and finance and education articles since 2011. Her articles have appeared on websites such as The Bump and Motley Fool. Measom received a Bachelor of Arts in English from the University of Texas at Austin.