I've never heard of a felt hat being called a "winter cowboy hat" but I don't mind it.
There's really 4 levels of felt cowboy hats if I had to think about it.
Level 4: This is going to be your American 1000x type of hats that are stupidly expensive just because they are made out of exotic furs and have gold buckles. These are not worth it unless you just want to spend the money to say you have a mink hat. I've only seen the cartel type wear these.
https://shop.besthatstore.com/amr-1000x-4-1-4-lte-lo.htmlLevel 3: These are going to be your Shortys and JW Brooks type of hats. They are truly custom made to fit your head and overall really good hats and worth the price if you are going to wear your hat just about every day. The 100x hats are worth the couple of $100 extra since they will last a lot longer than the 50x. These hats are what most performance horse trainers wear.
https://www.jwbrookscustomhats.com/https://shortyshattery.com/Level 2: This is where I would put companies like Catalena, Resitol's 100x hats, American Hats 100x and most other "custom hat" makers. If they don't build the hat to your head shape then they are not custom hats. They are just custom hat shapers. Any hat that is 20x or above would fall into this category as well. These are good hats and there are no problems with them, they are just not quite the level that the hats above are at.
Level 1: Any hat that is below 20x. Good hats and what 90% of people get because they are relatively inexpensive yet look good. Just be prepared to have to get it reshaped often the more you wear it. The less the x, the less durable it is and has a hard time keeping it's shape.
The most important part of the hat is the shape though. If you want to look at what hat shapes are in style just look at the hat shapes of the calf ropers who were in this year's NFR and go from there. Don't get some goofy shape that makes your nice hat look like it came from the Loves off of I35.