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Well, it will come as a surprise to nobody, but I'm already considering my next fedora.
As mentioned above, while I don't consider my fedoras "work hats," I do use them as a lifestyle accessory, like a jacket, gloves, etc... Therefore, I can see my fedoras as largely replacing my cowboy hats during the winter (we'll get to the Panama fedoras in a few months!). Firstly, fedoras are not as prone to being blown off, but they are also generally more comfortable for everyday wear, easier to wear in a vehicle, and they protect against the winter sun just as well. And they look so darn nice...
I've read about Akubras here, so I researched them and they look quite nice. Is it true they are one of the more weather "tolerant" fedoras? I like the Stylemaster, in either carbon or acorn. Also, it seems the Stylemaster has a bound edge; is that an advantage for durability, etc...?
Is there a "best" retailer to consider? Any sponsors of the forum? David Morgan seems like a logical choice but I'm sure there are plenty of others.
Akubra is a divisive brand: there are those who love them and those that hate them. I'm in the middle.
The bound brim gives it more finished and/or dressy look. It is not a durability feature.
If you are going to give Akubra a try I recommend going with an open crown hat. The Campdraft and the Federation IV come to mind. I tried the Fed IV and didn't care for it. I do like the Campdraft and I keep meaning to try the Squatter. The Campdraft is the best deal out there for new production economy hats as long as you like the proportions and the thin ribbon. Check out the Akubra Overload thread for more. Akubras do have a reputation for dealing well with bad weather.
As to retailers, you'll find that Akubra makes certain models and certain colors within a model as exclusives for various retailers. David Morgan is fine, but you'll pay re than if you order it from Australia. Everything Australian often has the best prices. The Hattery (Hats Direct) often has the best in-stock rates, and I've had good luck with Hats by the Hundred. And to keep you confused, some Akubras come if different quality levels within the same model with different felt and sweats. Lots of diverse options on this with several people claiming the lower priced hats have better felt!?! Not a lot of consensus.
Now to my biggest issue: fit. Speaking only for myself, I have not received two Akubras is the same size that fit the same. This issue is compounded it You order online from Australia where returns are long and expensive. Akubras are also know to "shrink to fit" as their leather sweats contract more than most.
Don't get me wrong, I still like Akubra. Do your due diligence and read up on them before buying.
At your hat size there are lots of fastastic vintage hats that are absolutely incredible. I'd focus on vintage if I were you.