I'm relatively laid back about my parenting. I like to encourage my children to make their own choices when they can. I let them pick out their own clothes when they want to (although more often than not, they're just as happy to have me do it). And for the most part, this works out really well. But both my younger two children have an affection for hats - and both are stubborn and insist on wearing the hat all the time. My son took a sun hat that I had bought for his older sister and wore it non-stop for three seasons. It was a little bucket hat, striped in bright rainbow colors and he flat out adored it. He wore it everywhere. And it was a little odd looking, but he was really happy about it, and I just let him go with it. I mean, it was a sun hat, it served a purpose. And he gave it up pretty willingly when it got cold and he needed a warmer winter hat. Now that he's five, he'll wear a hat if he has to, but is pretty much past the obsessive "I have to have my hat on all the time" phase.
My Julianna, though, I'm having a slightly harder time giving her free reign to choose her own headgear. And she's way more passionate about her hat that her brother ever was. At first, she just loved one of my older daughter's hand me down winter hats. It was pale pink and cute, and she wore it pretty constantly whenever we went out. Then she saw her older brother's batman hats, and instantly dropped the pretty pink girly hat for a rough and tumble batman chapeau. She's got a black and grey striped one, with the batman logo that she'll wear in a pinch, if she can't find the one she loves. But her absolute favorite is a black hat, with red flames along the edge and a red batman logo in the front.
She's sleeping in it right now. The other day, we went to a party at our synagogue, and she spent the entire time running around wearing leggings, a cute t-shirt, the red and black batman hat and striped mittens. I can usually get her to take off the mittens, but the hat is pretty much on her head all the time. It's not just for outdoor wear, it's an integral part of any outfit, including pajamas. She wears it for nap and even to bed at night.
She's a hat girl, and I wouldn't change it. I love that she's opinionated and passionate about her likes and dislikes. I'm just hoping that she's open to a summer hat or she's going to have a long, hot summer season.