[Moderating]
Let’s doff all the discussion about which sorts of hats look stupid, fucking or otherwise.
I just pull my fedora on as tight as I can get it. If it’s too windy for that then I have to travel one-handed, with the other holding my hat in place–kind of like how old-timey ladies had to walk around one-handed, with the other fully occupied in lifting their long skirts above the filth in the city streets.
My Tilley hat has a wind cord. I used it when I was in Egypt, because if the wind took it from me, there wasn’t anything to stop it until it got to Morocco.
N.B.: My particular model is no longer available, apparently, but the wind cord is still part of several models, from what I can see.
I am aware that some observant Jews, who wear a yarmulke (skullcap) at all times, may use a bobby pin or similar to hold it in place.
I have engaged in outdoor recreational activities lately that often entail getting hats blown off in gusts of wind. Hats with chinstraps were widely used. Also, hats with a flap in the back to keep the sun off the back of the next.
In direct answer to OP’s question, my suggestion would be to go with the hats with chinstraps.
Vlad the Impaler had his useful techniques too, but I don’t think OP would like that.
I can’t recall where I read it or what the time frame was but I remember reading a story once where young boys earned pocket money chasing down hats on windy days
I wear a ski cap for at least 6 months of the year. It keeps my head warm and cannot blow away. If you don’t like how it looks, that’s your problem.
My father wore a fedora very tight and I imagine he held on tight when necessary. What I was never able to understand was why his ears didn’t freeze since he never wore ear muffs. He said he got used to the cold and it rarely got that cold in Philly, hardly ever below 10 F. But still…
I have a Tilley hat. It’s a fine hat. but I’m not going to wear it with my suit to work. Maybe on days that I dress casually.
Where my Wife and I have gone horseback riding, you must have a chin strap for your hat. If it blows off, it can spook the horses.
A few years ago I had a batch of custom fezzes made by these folks for use at Burning Man, known for its occasional high winds. I specified some way of attaching a lanyard, just in case, and they came up with a small, sturdy loop at the back on the inside just short of showing.
I hadn’t considered that the city of Fez, where they were presumably thought up, also has a desert climate with a lot of wind. While I’ve not gone out with it during really windy periods – this causes what’s called a ‘whiteout’ where you want to hunker down in place anyway – but I have been hit by gusts I’d estimate at 30mph with no signs of the hat being lost. The lanyard loop had proved entirely superfluous.
Too bad that Capsurz cause cancer. Why in the world did Capsurz decide to use asbestos and fiberglass in their Capsurz products?