As a bald guy, winter can be a real challenge when it comes to staying warm. Finding the right hat that not only keeps my head warm but also stays put has been a long journey. I've tried countless styles, and I'm finally ready to share what I've learned. The struggle is real, but with the right knowledge, you can find a winter hat that works for you.
For years, I battled with hats that constantly slid off my head. It's not just annoying; it's also freezing! I remember one particularly windy day when my hat blew off and rolled down the street. I knew then I needed to find a better solution. I started researching different styles and materials, determined to find a hat that would actually stay put.
Through trial and error, I've discovered a few styles that work well for me. Here's what I've learned:
I found that knit fisherman beanies are a great option. Since they are usually a little more snug, they tend to stay in place better than looser styles. I shave my head every day, so having that extra grip is crucial. I’ve had good luck with beanies that are a bit thicker too, as they seem to hold their shape better and don’t stretch out as easily.
I even picked up a TNF Fisherman Beanie from The North Face. It was a little small at first, but after wearing it a few times, it broke in nicely. Now, it's one of the few hats that hasn't constantly ridden up on me.
Another style I've had success with is the scally cap. These tend to suit my head quite well. I found a great selection at Boston Scally. The key is finding the right size. Different hat designs will fit slightly differently, but once I got the size dialed in, everything has been great. It's a more stylish option than a beanie, but still provides good coverage and stays put.
While I haven't personally tried a trapper hat (I don’t live in extreme cold), I can see how it would be a good option. The weight of the hat itself would probably help hold it down, and they usually have a clip at the bottom for extra security. If you live in a very cold climate, this might be the perfect choice.
For those really brutal, windy days, a leather aviator hat (helmet) could be a game changer. The full earflaps help hold the hat in place, and the chin strap provides even more security. It's definitely a bold look, but when the wind is howling, practicality wins out over style. This is a great option if you prioritize function over fashion.
Recently, I've been exploring different beanie styles and came across a new handmade crochet hat from WholeCustomDesign Style. I was intrigued by the solid warm patchwork design and the idea of a handcrafted item. I decided to give it a try, and I'm glad I did.

The New handmade Crochet hats Winter women men solid warm patchwork sports knitted hat Warm Beanie caps Beige-Adult is surprisingly comfortable. The crochet design gives it a unique texture and a snug fit. It's warm enough for everyday wear, and the patchwork adds a touch of style. I appreciate the fact that it's handmade, and you can tell the quality is there. This particular hat has become a go-to for me on milder winter days.
While browsing WholeCustomDesign Style, I also noticed their commitment to unique designs and quality craftsmanship, which made me feel good about my purchase. It's nice to support a brand that values handmade goods.