I wear a hat of some kind most days. The two kinds of hats that I don’t wear are baseball caps and (unless the weather is in Arctic range) ski hats (the cap with a thousand names Knit cap - Wikipedia) because they’re fucking stupid-looking.
Sometimes I wear a beret but usually I wear a brimmed hat of some kind.
Yesterday I was crossing a broad, busy street (with the light, of course) and it was a bit windy, so I was using one hand to keep my hat on my head. Suddenly there was a gust so strong that it blew my hat away even though I was holding it.
(Luckily a nice driver stopped for me to retrieve it but it was pure luck that it stopped in a place I could get it and no one ran it over).
So do I just have to stick with brimless hats in windy weather or did men in the early 20th century have a trick to keep their hats on their heads? I specify men because I know women used hatpins and stuff to keep their hats on.
I wear a wool fedora on cold and rainy days. If it’s breezy, I tilt my head down and pinch the crown with one hand. I’ve owned it for about ten years now and I haven’t lost it yet, though I did lose a flimsier trilby to the breeze once.
“Never hire a man who rolls his own cigarettes, or wears a straw hat; if he’s not trying to roll a cigarette in the wind, he’s chasing that d*** straw hat all over creation.”
This. They were also sized way back when and fit pretty tightly - so a light breeze isn’t going to take it. I have my Dad’s fedora from the early 1960s and its a tight fit on my head.
Probably chin- or neck-straps in many situations but then alligator clips were invented; I’ve used a two-clip hat keeper since forever. Hat may blow off but it doesn’t go far. I just jam other hats down tight.
The OP question makes me wonder about earlier times before fairly low fedoras replaced tall top hats. How did Abe Lincoln keep that stovepipe in place?
The 2 styles of hats the OP eschews because of appearance impress me as among the 2 most practical styles of hats…
Not sure when it the last time I saw a man wearing a beret. But I CAN categorically state the last time I saw a guy wearing a beret and NOT looking like a doofus! That would be NEVER!
Unless, perhaps, he was in France, wearing a striped shirt, with a mustache, and playing a concertina… Nah, he’d still look like a doofus!
The peaked cap often worn by military and police (though increasingly only in a formal dress uniform) has a strap that goes across the front, just above the base of the brim. You might think it’s for use as a chin strap. And maybe, back in the day when such hats were worn as practical header, that’s what the strap was used for. But now? Strictly decorative (even though it is often capable of being brought down under the chin).
Anyway, I nearly lost my headgear to many a sudden gust of wind while walking along piers or up the ship’s brow (the gangplank, if you will). It was blown off and sent flying more than once, but every time, I managed to catch it before it ended up in the water. Often only just.
Perhaps also that they would also use some sort of hair tonic/oil or whatever. With short hair and some sort of… elixir? I bet you could get a pretty snug fit.
