Underpants on His Head? Letting Your Child Dress Himself

“I do it myself!” This is a common toddler refrain, but when it comes to getting dressed themselves, toddlers can come up with some charmingly odd outfits. Underpants on his head anyone? So when is the right time to let him make his own fashion choices?

“Whenever he shows he’s interested and ready, which is typically around age 2 or 3,” says KinderCare Education’s Christine Pieper, director of quality and accreditation and an early childhood education expert. “At that point, he should be allowed the opportunity for this freedom of expression and to practice his getting-dressed skills—but with certain parameters and limitations.”

In other words, when it comes to clothes and tots, you’ll want to pick your battles. Here are five common sartorial scenarios for toddlers—and Pieper’s tips for handling them.

1. You’re going to a fancy wedding.

Henry wants to wear … shorts and a Pokemon T-shirt.

Solution! Get ahead of the situation. When there’s a special occasion coming up, select a few options and let him choose: But remember that you need to be okay with whatever ensemble he settles on, even if it’s not the combination you would have chosen yourself. In giving your child limited choices, you’ll satisfy your own needs, nurture their growing independence, and potentially avoid a tantrum.

2. You’re going to the grocery store.

Stella wants to wear…the fuzzy kitty-cat footy pajamas she loves, loves, loves, loves, loves.

Solution! Let her. What children choose to wear is a reflection of their own personality, not of yours, so don’t be embarrassed. Remember she’s three! She’ll eventually notice that people don’t wear pajamas to the store and, with your guidance, make new choices as she grows and matures.

3. You’re running errands—and it’s below freezing.

Caitlyn wants to sport her favorite rainbow swimsuit.

Solution! While presenting your child with options for appropriate alternatives is a great way to prevent fights, it’s also okay to compromise: If she’s really all about that swimsuit on a chilly day, explain that it’s fine at home but she’ll need to put pants and a jacket on over the suit before going out. You always want to ensure your child is safe and warm, but allowing her some autonomy over her body builds important social-emotional skills and self-confidence.

4. You’re going to the park.

Lily wants to wear her tutu—and nothing else.

Solution! Talk about it. Explain that while certain ensembles might be fine for staying at home with family, when we go out in public spaces, we keep certain parts of our bodies covered. Keep it positive, being careful not to use any words that might make her feel ashamed about her body. Use mommy, daddy, and other friends you see out as examples. You can also talk to them about their physical comfort: playing in sand, sitting on benches, etc. can be uncomfortable without proper covering.

5. You’re going to preschool.

Lachlan dressed himself, but his shirt is on inside-out and his pants are on backwards.

Solution! Practice, practice, practice—knowing the proper way to put things on is a learned skill, like writing or using scissors. Around age 2 or 3 children are only beginning to master the gross motor skills it takes to, say, put on pants. It’s much easier to take things off, which is why you might frequently have a naked (and proud) 18-month-old on your hands! If he got things wrong, put the focus on what he did well: Great job getting your shirt over your head! How about I help you turn it around? If he responds with a “no,” consider letting it go. After all, that backwards shirt will seem pretty minor compared to his big grin.