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mine always did better with sun hats that had a strap or something to keep them on
 

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I have better luck with the ones with a strap-especially the straps that Velcro since they are so adjustable. I've actually added straps to hats to help DS keep them on. It's still a limited time thing, but every once in a while he'll wear one for a long time if it has a strap.

DH also wears a hat often so I show DS that he can be like daddy when he wears his hat-that sometimes help keep the hat on.
 

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Definitely a strap and I just keep putting it back on when a toddler takes it off. We live at a high altitude, sun burns happen quickly so not wearing a hat isn't an option.
 

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Sorry, I'm not of much help. DS won't even keep the ones with straps on. He has figured out how to undo them so it is just a constant battle to keep the hat on his head.
 

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Baby Banz (I think that's the brand) sunhats have a built in elastic and velcro tightener to make hat fit on and be less likely to fall off.

We also have a rule - no hat means we go inside (worked for us as dd loves being outside). dd (25 mo) can put her hat back on herself which has also helped.

The other great ones are the ones made of lycra/neoprene designed for the water - looks like a ball cap with a flap on the back to protect neck/ears (sorry can't remember brand).
 

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My toddler has a gigantic head and the ONLY hats I could find that fit him that also have a strap are Hanna Andersen. He has the 2T size and he will wear it... uh, sometimes.
The strap is a tie-strap, though, and not velcro. I don't know why they stop making strap hats for toddlers at 12M. Annoying!
 
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