The cool thing about always wearing a hat is...

[Ordinary Guy]

The coolest thing about wearing a hat is Free Gelato.....

A couple of months ago, I stopped at a Gelato stand and ordered a small.

The lady waiting on me, said here is your order sir and I really like your Fedora, and handed me a LARGE Chocolate Gelato, I said but "I ordered a small". She said, "I KNOW" and charged me for a small and gave me a wink......

 

[Midwest Boater]

some poor gent in a P.G. Woodehouse novel lost his hat in some or another misadventure so he went to a cottage to barrow one no one was home so he did the only reasonable thing , he broke into the place to snag a hat so as not to be seen walking around with a naked dome.

 

[Belegnole]

The cool thing about always wearing a hat is... well, that I am just being me!

I'm not trying to fit into the crowd, be accepted, etcetera. Plus as someone else said....no more bad hair days!

Oh! also you can change your look in a moments notice just by removing the hat.

 

[Edward]

OP statment does not compute. Aside from when it is simply polite to remove a hat or I am certain places indoors, I always wear one. Even, when it's cold, wear a beret at home (in lieu of a smoking cap, at least for now - either a French-made Basque beret or an old German military one with a Soviet star on it from a costume party I went to as Ched Guevara years ago). It's just now second nature for me to wear a hat.... the only second thhought I give it is whether it coordinates, or whether a cap might be more appropriate than a brimmed hat (if I'm going somewhere that I need to stick the hat in my pocket rather than having somewhere I can put it).

Just by virture of wearing it to the gig, you've already made a statement.
No need to ruin the hat with sweat while rockin' out on stage. Besides, the hat looks really cool sitting on top of my amp.

What really winds me up at the minute is folks wearing hats inside in clubs and whatever. It's part of what folks interpret as a period look, I suppose, so they wear it all night, but IMO that's when it becomes costume rather than clothing.

Did love old BB King's schtick when he has a flunky bring on his coat and hat at the end of the gig, and help him into them before he leaves the stage.

 

[Edward]

When I was younger I must say I enjoyed the attention but now after experiencing some negative attention in foreign hellholes I will at times refrain from wearing one. Not often though.

Only palce I ever remember my hat being remarked on constantly was in China... all very positive comments. I inevitably kinda stick out there ayhow, so that never bothered me. Course, China ain't no hellhole anyhow.... love that country.

I quite frankly have grown to actually dislike going out without a hat, especially in any season other than hottest summer, perhaps. I even wear a hat inside the house, except when there's visitors. Other than that, I do follow the usual rules of etiquette pretty much to the dot, question of style.

When I started wearing fedoras regularly, the only time it really made much of a difference was Spring / Autumn.... for several years I'd already been wearing various caps (yachting style, mainly) in the Winter and Sun hats in the Summer (GI Boonies, Vietnam-era style). I suppose you could say I had the practicality angle all covered before I chose to start wearing hats for the look of it...