How to keep a fedora in place on your head and not blown away?

Like Indiana Jones. Staplegun!

Bobby pins.

This is the classic fix for things like this—in essense, use a bobby pin or two to pin the hat’s inner band to your hair. It won’t get you 100% protection.

There are also hat pins, usually for women’s hats. You stick the pin thru the hat, catching some hair in it. This is assuming you have hair. http://www.goantiques.com/scripts/images,id,1992347.html

Sooperglue! :D

Get a smaller size that holds on to your head more tightly.

@drdoombot: A smaller size would pop off more easily, or if not, give you a nasty headache.

@drdoombot the size is already the smallest size it’s a s/m they didn’t have xs/s

How about the things you can put on the inside heel of a shoe so that it won’t slip?

Stitch a strip of broad elastic about 3” long inside the hat at the back, parallel with the hat-band, so that it’s tight and pulls in a bit. (hard to describe without a picture).

I wear a trilby that’s a size too small (I actually found it in a children’s store) and it doesn’t pop off, blow off or give me a headache, but it does make my head itch if I wear it for too long.

If you look at the crown of the hat, you’ll see around it a string with a button. Carefully pull out that string. Make two ¼ ” incisions in the brim just over where your ears are. Slip the string thru one hole and out the other, then tuck the button back into the hatband and tighten as needed. Now you’ve got a chin strap to hold your hat in place! The excess string will dangle inside the hat when not in use, but that’s a minor annoyance compared to chasing the hat down the street!