Why not carefully poke 2 holes and thread a long scarf through it and use that for securing a fly-away hat from airborne status?
A pretty scarf also can dress-up the style worn.

Look at some of those fancy sunhats online for a idea of how to encircle the hat for best result...
:runninghorse2:...

 

I am in Wyoming. We get wind.

Western hats are available in different shapes. Oval. Round. More rectangular.

And with straw hats, I do use a stampede string. I run the string behind my ears and the ends on my chest. That way, regardless of which direction a huge gust hits me, I have a chance of not losing my hat. I've only had one come off one time.

My felts always stay on.

It's not a dumb question either. Learning what hats will work for you takes a lot of trial and error, or someone to help. Good, real, western stores have clerks that can help. The folks in many chain stores have no idea.

Most people go for the look of the hat first, when that should be the last thing to consider, if you really need a functional hat.

 

@ACinATX Watch an old Randolph Scott movie. He always uses a stampede string. His also has a bead on the string so he can tighten it up under his neck.
And he always used the same beautiful horse in his movies that I have watched

Just go to utube and watch his movies.

 

Very interesting, I didn't realize people wore strings with cowboy hats. Can you get a hat that already has a string, or do you add it yourself?
@horselovinguy that's a really good idea.

 

Very interesting, I didn't realize people wore strings with cowboy hats. Can you get a hat that already has a string, or do you add it yourself?

@horselovinguy that's a really good idea.

Ahhh. There probably are hats that have strings attached, but strings can be art on their own. Rawhide, leather, horsehair. Natural or dyed.

Get one you love.

 

I have a weird shaped head, its round but not. The oval hats don't fit either. Any hat preshaped, out of the box, I try to wear looks like I put it on sideways.
My good felt I keep for shows is custom made, you should see the shape of the form that stays in the hat when it's not being worn..lol... I think my mom dropped me on my head a few times as baby..

Anyhow, my point is fit has a lot to do with it staying on. Also one thing I was doing was buying a hat too small to mush down on my head. I used Bobby pins, stampede strings, double sided tape, hairspray, it doesn't work!
If a hat fits well it will be snug but not tight or give you headaches after wearing a short time.
I was trying to cramp my head and hair into a 6 7/8 but after getting a hat fitted I really wear 7 1/8. It made the difference in wearing a hat all long in the wind or at a high lope without stampede strings. Admittedly if the wind is going to be blowing hard(25mph+), I wear a ball cap as I hate the feeling of the wing tugging on my hat. It makes me cranky.

I like the American straws. I have one I have been wearing for several summers now for show and work. All my hats have a 5" brim and I have no issues with keeping it on and I love the vented tops. It feels so good on a hot day when your head is sweating a bit, you strike a trot to create a little breeze over the top of your head-air conditioning!

I'm not saying you need to go out and buy a custom hat but I'd get your head measured and get a hat that fits.

This is the straw I have. Note the ventilation.

 

Tilley T3. Mine has stayed on well without using the string, but the holes are built in if needed. Plus vent holes, made of cotton, and you can snap up the sides if desired.

In honesty, though, I try to avoid riding in strong winds. We had gusts to 40 mph yesterday and I just said, "No thanks!"

 

I've got a half a dozen or more cowboy hats...and pick the one I wear based on the weather forecast....It's all about the fit.....I'm a long oval, and use a hat Jack to fit them perfectly....

 

One that fits well won't blow off, particularly one that's felt and has been 'worn-in'. The only one's I've ever had that didn't stay on in strong wind were palm/straw in the summer because the fit changes when those get wet/damp with rain or sweat, and then dry. A stampede string will help in that case.

 

If you have an extra one, that is perhaps on the large size, you could consider making a "Hell Hat". This is a hybrid between a hat and a helmet, and gives you that shade, but also the safety of a helmet.

 

Yes, snug, not tight, fitted to the shape of your head and for the ones like bsms pictured a string. My straw sun hats that I used to wear in Tx all had holes for a string or a string. The strings can be works of art. HLG had a great idea with scarves if they are thin enough.

 

Hats come in a variety of shapes as well as sizes. Try as many as necessary to find one that actually fits. It should be snug but not tight. The sweat band also plays a large part in comfort and ability to keep the had on under windy conditions.

Experience helps teach how one should adjust the hat and head to keep the hat on when windy. Still, there are times when a stampede strap is necessary.

 

The only time I wear a cowboy hat is for showing and I make sure that sucker ain't coming off! My hair is up under my hat so it's pretty easy to use long Bobby pins through the seams of the inner brim into my hair, that way I don't damage the hat. That hat won't come off unless my scalp goes with it! It will also work if your hair is in a pony tail.

 

Put this in the search bar: women sun hat with strap string ties


Here's one. There are others.

 

It's hard to change the shape of a hat.....but once you find the right shape buy the hat a little tight, then use the hat jack to stretch it for the perfect fit. If I don't wear it for a few weeks then I usually have to Jack it over night as mine seem to shrink just a bit over time. Google hat jacks.....