How to Keep a Hat on Your Toddler

How to Keep a Hat on Your Toddler

You put the hat on. Your toddler pulls it off. You try again, and suddenly getting out the door turns into a negotiation over headwear.

As a mom and an apparel designer with more than 16 years of experience, I think the best place to start is with three things: how the hat fits, whether your child enjoys wearing it, and how it fits into your everyday routine.

Full disclosure: my own child has always naturally liked hats, so I can’t claim I discovered a magic solution through months of hat battles. But developing Pickleberry Kids hats and watching other children interact with them has shown me how much comfort and a little personal choice can matter.

Start With a Hat That Fits Correctly

Before trying to convince your toddler to keep a hat on, check the fit. If it’s uncomfortable or constantly slipping, they have a reason to take it off.

One thing I look for as a designer is where the hat sits on the head. A hat that sits too high may be too small. A hat that slides around or drops into your child’s eyes may be too big.

For Pickleberry hats, I also use the adjustable hook-and-loop closure in the back as a sizing guide:

• Consider sizing up when the closure needs to be extended about halfway to fit comfortably.
• Consider sizing down when you need to overlap the closure by about halfway to get a secure fit.

Those are my guidelines for our hats, since closure lengths and proportions vary between brands. The goal is a comfortable fit that stays in place without needing frequent adjustments.

Give Your Toddler Something to Choose

One of my favorite experiences with Pickleberry happened when I gave a friend’s child a hat.

His mom warned me that he didn’t like wearing hats. But when he could put something he liked on the front, his reaction changed. He was proud to wear it and didn’t take it off.

That moment stuck with me. Choosing what went on his hat gave him a reason to be excited about wearing it.

Pickleberry hats have interchangeable patches that kids can choose and swap themselves. The interactive part is something I believe makes a difference: they get to help create the hat they’re going to wear.

If you already have a hat at home, you can still offer a simple choice. Try asking, “Do you want your blue hat or your green hat?” With a patch hat, that might be, “Which patch are you wearing outside today?”

I wouldn’t promise that choosing a patch will turn every reluctant toddler into a hat lover. But I’ve seen it make a difference for a child who previously didn’t want to wear one.

Make It Part of Your Outdoor Routine

My recommendation is to make the hat a familiar part of getting ready to go outside.

Shoes on, hat on, out the door.

Keep it near the shoes or whatever else you grab before heading out. That gives you a natural moment to offer it each time, whether you’re going to the park, playing in the backyard, or taking a walk.

You can keep the language simple: “Let’s grab your hat before we go play.”

The idea is to make wearing it an ordinary part of the day, with a chance for your toddler to participate by picking their hat or patch.

Show Them What the Brim Does

Toddlers may not care about your reasons for wanting them to wear a hat. But shielding bright sunlight from their eyes is a benefit they can notice.

When the sun is bothering them, show them how the brim creates shade. You might say, “Your hat helps keep that bright sun out of your eyes.”

I like this approach because it connects the hat to something useful in their world. They can feel the difference while they’re outside playing.

Keep the Experience Positive

If your toddler keeps removing their hat, I would return to the basics before assuming they simply won’t wear one.

• Does it sit comfortably on their head?
• Is it slipping into their eyes or sitting too high?
• Can they choose something about it?
• Are you offering it consistently before outdoor play?
• Have you shown them how the brim helps with bright sunlight?

My own child came by his love of hats naturally. My friend’s child needed something that made him proud to wear one. Your toddler may need a little experimenting, too.

From my perspective as a designer and mom, a comfortable fit, a chance to make it their own, and a familiar outdoor routine are good places to start.