Biltmore used to be Canadian but was purchased by Stetson. They are a decent fur felt hat. I have one in a stiffer western feel to it but the style is that of the country gentleman between western and fedora. They offer a decent value for the dollar. Also check out Sewmaster53 on Ebay. They are a dead stock/sample hat Stetson reseller at least 50% off the retail.
Alden 403 Moc Toe Boot - Brown Chromexcel - $680 The classic "Indy" style Alden Boot in the classic Horween brown Chromexcel. 
Grant Stone Diesel Boot Dark Olive Chromexcel - #395 Goodyear welted, Horween Chromexcel, classic good looks. 
Himel Bros. - The Ross Mk. 1 Leather Jacket Classic D-pocket motorcycle/aviator style jacket. 
Welcome to the forum Mr. Rack. Hip is in the eye of the beholder. I would suggest some "required" reading, the Links to Important Hat Forum Threads will have answers to just about any question you could come up with. Fur and straw hats are in your future.
Visiting that store really threw me off. I don't doubt the quality of their stuff, but what do I know. I knew stiffeners were added to hats, maybe they weren't added yet? I am not sure what a hat is like without stiffener.The condensed version:
1) The "softness" of a hat can mean two things that are slightly related, but also, not. There's the malleability of the felt and then there's the actual tactile feel. The former is more related to the quality of the felt itself, as well as the addition of stiffener, while the latter is related to the material and the time and effort spent finishing the hat.
Modern western hats are fairly stiff.
2) Most fur felts should be fine in the rain. Some caveats apply. Generally, wild hare is favored over rabbit, and beaver is favored over wild hare in terms of water resistance.
3) Yup, summer is straw hat season, you need one of those too.
Thanks for the link, I will look into it. And believe me, I would have many more hats if the Mrs. understood what owning a hat meant.
My fitted ball caps are 7 3/8. I'm not sure where that lands as far as large or small. I do know it doesn't take long for them to shrink if I don't wear them enough.
Welcome to my world. Don't worry, after a while, they cease to notice...
Somewhere here on The Lounge an informal poll was conducted and the results showed 7-3/8 (59) and 7-1/2 (60) were the most common sizes among the members; if I remember correctly, 7-3/8 took first place by a narrow margin. If that's true those sizes would be right in the middle between "small" and "large", but I think most people consider 7-3/8 to be on the low end of "large".
Thanks for the tips. I'm not necessarily looking for a western hat by name. Cowboy hats tend to be lumped into that label as well, and that's not what I'm looking for. Like you mentioned, I'm after the more rugged look. I like the pinch front and at least a 3" flatter brim. I'm learning fast that they are usually not soft. A firm crown doesn't bother me quite as much, but a brim with a tad bit of give was ideal. Like I had mentioned earlier, a visit to Az-Tex threw me off not knowing much about hats. At the end of the day, a comfortable piece that looks good and is well worth the money is what I'm looking for.
I guess I'm having trouble differentiating between a western and a fedora, or more specifically, what exactly you describe as a fedora. Are you referring to a more stylistic short brimmed version? I mentioned before that my love for hats began with the Indy (which I know were different styles for each movie). I also like the more rugged look with a casual feel, if you catch my drift. If you've ever seen the tv series Justified, the main character wears a custom Stetson. It's got somewhat of a rugged look to it, but he wears it with style. Although I don't want that exact hat, that's the look I'm going for. Now it's been mentioned before that fedoras tend to be softer than westerns, is that why you suggest me looking into customs?
Will less stiffener diminish the quality of the hat, or how it will hold up to the elements? I am not sure of the purpose of stiffeners, other than to make the hat stiff.
Yeah I get it. With a lot of things these days, they cheapen the way they make things to lower the cost of manufacturing. I can see where a lot of those things are important to people. At this point, I'm not enough of an aficionado to take those sort of things into account. I'm just trying to get myself a nice hat that will last several years before I get my next oneAgain, this is the condensed version. A deep dive in the lounge will reveal nuance, caveats, and varying opinions.....above all, buying vintage is always kind of a gamble (sweatbands shrink; dry out; sometimes smell musty; sometimes are measured by sellers, etc)
That being said, we go through all the effort because the average vintage hat is just better made than the average hat today. This is due to a number of reasons, some are more opaque to the consumer than others. Mercury processed felt a being notable example of how the production process has changed. Vintage ribbons don't have synthetic fibers. The attention to detail was generally greater. The ribbons on modern Stetsons (which are technically produced by Hatco, licensee of the Stetson brand) are affixed with clear poly thread...think fishing wire. Why do they do this? I guess changing spools of matching threads is too tedious...or they ordered too much poly thread some time in the 70's and are still trying to use it up. It's the kind of thing that you might not have noticed until it was pointed out. Especially if all you've ever seen is modern hats. But the ribbons on vintage hats are tacked on neatly, near the finished edge of the ribbon, so as to hide as much of the stitch as possible.
No, really, I swear this is the condensed version.
generally a firmer hat will soften with age and exposure to the elements. There are also techniques to remove some of the stiffened using denatured alcohol.
I've always liked the Dune in the Gun Club collection. Somewhere between Aussie/Western/Fedora:
https://www.delmonicohatter.com/Stetson/SF04161139.htm
.