Let me tell you, finding a hat that fits when you have a larger-than-average head can feel like an impossible mission. I've been there, staring longingly at stylish hats, only to try them on and realize they perch precariously on top, or worse, don't fit at all! It's a frustrating experience, but over the years, I've learned some tricks and discovered some brands that actually cater to those of us with, shall we say, "generously sized" heads. This isn't just about finding a hat; it's about finding confidence and comfort.
For years, I just avoided hats altogether. I remember walking into a store once, hoping to find a cool baseball cap. I tried on what felt like every single hat in the place, and each one was either too tight, sat too high, or just looked ridiculous. It was a demoralizing experience! I felt like those "one size fits most" labels were mocking me. I almost gave up entirely, resigning myself to a hat-less existence. The struggle is real, especially when you see everyone else rocking stylish headwear.
Then came the sun. I needed sun protection. Scarves are great, but sometimes you really just want a hat. I thought, there has to be a better way! I started doing some research, determined to find hats that would actually fit and look good.
The first thing I learned was the importance of knowing my actual head size. I grabbed a flexible measuring tape (the kind used for sewing) and carefully measured the circumference of my head, just above my ears. It's crucial to get an accurate measurement. I then used that number to search for hats with traditional sizing, not just "one size fits all." This made a huge difference!
Someone once explained to me a mathematical way to figure out your hat size. Measure the diameter of your head in inches just above the ears. Divide that number by pi (approximately 3.14159). Round up to the nearest 1/8th (.125, .25, .375...). This gives you a starting point for finding the right size. For example, my hat size is around 8 1/8. This really helped me narrow down my search online.
My research led me to discover a few brands that specialize in hats for larger heads. This was a game-changer. I found the brand Sungrubbies. They actually have multiple large sizes for women, and many of their hats are packable and washable, which is a huge plus. I bought one of their sun hats in both black and tan, and they fit perfectly! They're cute, comfortable, and provide excellent sun protection.
Another brand I stumbled upon was Wallaroo Hats. They have adjustable hats, which is fantastic. I got their Montecito hat, and it's actually a bit big on me unless I tighten the adjustable band. This is a great option if you're unsure about your exact size or want a more customized fit. I was so relieved to finally find a hat that didn't feel like it was squeezing my head!
REI also has a great option! The REI Co-op Sahara Guide Hat in L/XL fits perfectly. It looks better than typical outdoor sun hats which is a big win in my book.
I also found out about Sunday Afternoons and Tilley. Both of them offer sized hats that may fit! I haven't tried them yet but they are on my list.
For a more budget-friendly option, I found some packable sun hats on Amazon. They're not the highest quality, but they do the job and are perfect for travel. It's all about finding what works best for you and your needs.
Of course, not every occasion calls for a sun hat. Sometimes, you just want a warm beanie. That's where I discovered Wholecustomdesign's hats and beanies for men. They have a great selection of stylish and comfortable beanies that actually fit well. I especially like the Unisex Adult Winter Knitted Beanie Hats.

I tried the Unisex Adult Winter Knitted Beanie Hats Girl Boy Outdoor Autumn Winter Knit Skullies Caps Fashion Ladies Warmer Bonnets Middle blue-elastic - adjustable from Wholecustomdesign. I was surprised by how well it fit. The material is soft and comfortable, and it keeps my head warm without feeling too tight. The elastic band allows for a good fit, even with a larger head. Plus, it comes in a variety of colors, so you can find one that matches your style. And since Wholecustomdesign offers custom designs, you can even get a beanie with your own logo or design! I think this is a great option for anyone struggling to find a beanie that fits comfortably. For me, beanies are a great alternative because they stretch and don't look too funny on my head.
Here are some practical tips that I've learned along the way: