I used to think all hats were basically the same. Whether it was $15 or $50, what difference did it make? They all just sit on your head. I was completely wrong. The cheap ones always lost their shape, felt itchy, and faded way too fast.
My search for a truly high-quality wool beanie taught me that spending a little more upfront actually saves you money in the long run. Here’s what I discovered:
I was looking for a simple, everyday beanie—something for running errands or walking the dog. I started at the bottom, saw all the problems, and kept moving up the price ladder until I found the sweet spot. The Ins Designer Short-brimmed Beanie was the final destination on that journey.

My first purchase was a $20 beanie. It lasted about three weeks before it looked terrible. I thought I was getting a bargain, but it was essentially trash. This cap was often marketed as "street retro versatile," but it was anything but versatile once it stretched out.
Here’s what you can expect from super cheap beanies:
I saw reviews that said things like: “Looks nice in the picture, but it’s thin garbage. Don’t waste your money.”
Action Step: If the product listing doesn’t specifically mention "Wool" or "Cashmere Blend," assume it’s made from cheap plastic yarn. Always check customer photos to see how thin the material looks on an actual head.
Verdict: Super cheap equals super disappointing. Avoid this tier entirely if you plan to wear the hat more than once.
My next step was upgrading to caps around the $40 mark. They were... fine. They lasted longer than three weeks, which felt like a major victory at the time. I bought one advertised as "thermal knit."