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Great post! I completely follow your reasoning there, even though I find myself walking a different path.
I've always liked hats, but typically been a one hat guy, or should I say one mid winter hat, and one summer sun/rain hat. Now I find myself expanding a little, but cautiously so. I'll try to give some perspective, although as I'm still trying to understand my own perspective, what I say may not be entirely accurate.
To my mind, there's accessory hats, and working hats. The following hats are what I would consider working hats.
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Both of those are great in terms of function. The wide brims being great at protecting me from the elements. However, neither hat is what I would go shopping in, or wear if going out for a meal etc. They're home use (either mine, or friends or family), in the garden, either doing jobs that need doing, or enjoying a drink and BBQ.
On the other hand, these two are ones I'd consider accessory hats.
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The narrower brims aren't as functional against the elements, but both look better on me for going about a daily life in a public setting. One is good in sun, and the other will keep my head warmer. I have another that is my go to rain hat, a weathered look cotton trilby. Three more are needed for my out and about primary six. I have my eye on a Christy Foldaway and Tilley tecwool hat for dressy functional, and for mid winter. I don't particularly need more in terms of working hats though. Maybe what some would consider beater hats.
As for character, I like new hats. I like them more when they don't look new any more, and knowing that every crease, stain, scuff, or hole, is a story from my life, not just an unknown impairment from someone else's. In fact that's quite close to my thinking... if I put it there, it's character and welcome, but if someone else did it's an unwelcome blemish.
As to collecting... nah, not for me. Too many choices as what to wear, too much stuff to find homes for, hats taking too long to develop character as the stories are spread across too many items. I'd rather have a select few and beat the snot out of them. I also appreciate that some of my hats might not to be up to the task in terms of longevity, and are merely placeholders. That's fine. If they get wrecked and need replacing, I know it's the right type of hat. If it sits sulking and neglected, it's the wrong type of hat, but doesn't matter, because it was just a cheapie.
Time will tell where the big money needs to go, and for the most part, will go to replacing the most quickly wrecked cheapies. In essence, going towards needs, not wants. If I fancy something of a different type just for the heck of it, it will be uber cheap. My grey bowler will never be a primary hat - I just wanted one. Less than £20 scratched that itch successfully
Sorry, rambling post, but I hope I've given some clarity. Six primary accessories, a couple of working hats that the public don't have to be subjected to, and a couple of novelties for the fun of it. That's me quite content.
I certainly understand your perspective, even if it isn't my own. One thing to also consider if soliciting advice from this crew is to reflect on this site's purpose and mission. Though we certainly deviate from it, the FL stands for the appreciation and preservation of the Golden Age. So most of us are quite enamored of the Old, whether it be clothing, lifestyles, machinery, cars, etc. This stuff gets our blood flowing, and gives us a different perspective.
Take, for instance, your definition of a work hat/beater, and a dress hat. Of course there is nothing wrong with it, but from the perspective of many on this site, a work hat is still a fur felt hat with similar dimensions as a dress hat.
Take a look at this thread: https://www.thefedoralounge.com/threads/the-non-shorpy-web-all-stars.56296/
This thread explores how folks dressed and conducted themselves in everyday life during the Golden Age (and often beyond). You'll see fur felt "dress" hats being worn in a variety of ways while doing everyday things, like working in a factory, going from place to place, or just living. Hats with dress clothing, work clothing, sometimes no clothing! (https://www.thefedoralounge.com/threads/woman-wearing-hats.79647/). Many folks on here study this exetensively, and the hardcore ones carry it a bit further with a certain bit of LARPing.
I've come to appreciate wearing a brimmed fur felt fedora with pretty much everything - shorts, jeans, a suit, whatever. It can become as natural as putting on a pair of pants.