This one is super random but it’s something that’s going through my head so I am going to share it like the oversharing doofus that I am, run on sentences and all.
Hats. Should I have a go-to hat look? I have been a baseball hat guy since I was seven years old. Unfortunately as an adult I have a SUPER large head and it is hard to get baseball hats that fit. Those one-size-fits-all bastards? Not even close. Liars. I found a store that sells sized, licensed baseball hats (actually, I think Jen found the store) so I have a Red Sox hat that fits, though it feels a smidge too big post-weight loss surgery. I think my skull might have lost a little weight along with the rest of me.
Anyway…
We were watching The Gilded Age on whatever streaming service it’s running on… Max, maybe? Whatever, it takes place in the 1880s or 1890s and all of the men wear top hats. I asked Jen if I should wear a hat like that. She said yes. I think she was kidding. It got me thinking though… should I be a hat guy? Should I have a hat look? Maybe like a bowler hat like the characters in A Clockwork Orange? What about an Irish Scully Cap? My red hair makes that a pretty obvious choice, doesn’t it? What other types of hats are there? Not a cowboy hat, screw that redneck noise.
Is this something I should research? Is this something that I should make happen? With Jen’s approval of course. I don’t want to decide on a look that she wouldn’t like. The idea, as with all things, is to impress her and make her want to keep me around. You know how it is.
Thoughts?
Inside the Red Head's Head 
Maybe a fedora, like Indiana Jones? Or maybe a pith helmet… LOL
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Ah, go classic! A Fedora with its timeless quality—Classic, versatile, and a touch sophisticated without being pretentious. Or a Panama in the warm climate. Both would work. Cheers!
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Get a good Derby or Bowler.
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First of all, love your self-description of oversharing doofus. I see you! I am partial to the Irish Scully cap. I brought home the Scottish version of same from Edinburgh last year. He has big old head and it fits him perfectly and makes him look even more handsome and debonaire.
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