I used to think all baseball caps were the same. You just needed something to cover your head on a sunny day. So, I always bought the cheapest one I could find.
This was a mistake. I wasted hundreds of dollars over the years buying caps that fell apart, faded instantly, or just looked cheap. I finally learned that paying a little more buys you a lot more.
My journey went from the $15 bargain bin hat to the $49 premium cap. Here is why the big jump in price is actually a smart move.
Upgrading your cap means:
My first few caps cost about $20. They were the ones you grab at the airport or the big box store checkout line. They lasted maybe three weeks of actual use before showing major problems.
The Reviews Were Bad: These caps often had 1- or 2-star feedback if you bothered to look.
The biggest issue was the material. The cheap caps use thin cotton or polyester. The brim often had cardboard inside, so washing it made the brim permanently wavy. If the cap was supposed to be a nice tan baseball cap, the color usually looked sickly yellow after a week.
Verdict: Skip this phase entirely. You are throwing away money. This cap is good only for single-use events, not for actual wear.

I upgraded to caps in the $30 to $40 range. They were... fine. They did not fall apart immediately, and the stitching was a bit stronger. This is where most people stop their search.
The problem is they still felt generic. They did not have any character or special fit. They were just standard caps.