Most comfortable hat I have

[Rabbit]

The wicked comfy chair among my hats - these are ones where I keep checking if they're actually on my noggin. The others are just plain comfy. lol

Montecristi Panama 800 wpsi blocked by Art:

Montecristi Panama 600 wpsi blocked by Art:

VS Silvermist LITE:

Borsalino Natalsca Bismuto, unreeded sweat (1940/50s):

Mallory heather blue, unreeded sweat (1930s):

 

[bowlerman]

Hey Rabbit-- do you think there's something different in the comfort of heathered felt from regular felt? My heather green Borso would be a pretty close second for barely knowing it's there.

 

[jlee562]

The most comfortable hats I own are this vintage Resistol "Gotham I" with their "self conforming" sweat:

And my Black Sheep custom:

 

[Rabbit]

Hey Rabbit-- do you think there's something different in the comfort of heathered felt from regular felt? My heather green Borso would be a pretty close second for barely knowing it's there.

I wouldn't know if there's anything inherently different about it.
From my limited experience, the factors that can make a hat wear like it's barely there, are (apart from just plain fit, obviously) thin felt, least possible stiffener, and sweatband construction. My three unreeded Borsos from the 1940/50s are extremely easily conforming sweatbands, but so are some of the reeded sweats. For straws, a high count Monti with barely any stiffener feels like air.

 

[scottyrocks]

I have some vintage fedoras, three Feds, 2 IVs, and a III, and some others. The most comfortable is definitely my very soft, well worn III. I got it very well used and just did a reversal on it, as a hole was forming at the top of the pinch. I was very happy when I put the whole thing back together and it was a comfortable as before I took it apart.

Post-reversal:

Pre-reversal:

 

[Lloyd]

has to be my VS Artlite Pecan

 

[tealseal]

Mine is, without question, the Custom I'm saving up for However, in the current collection, I'd say it's a toss-up between my Cervo and my Federation.

 

[99benzman]

My Rio Grande Hatters custom fedora

my Rio Grande Hatters Custom Lonesome Dove

and my Knox Straw