This is a helpful thread! my head's about regularly sized, but i have to try on about 50 hats before i find one that looks good. I wear hats a Lot, as i am very fair, so i understand the frustration factor.
We have a few Tula brand hats in the family. They're very well made and come in a variety of really flattering designs.
The Ava is big, not so floppy, but is meant to sit up on the crown and stays on with an elastic you nestle under your hair at the nape:
http://www.tulahats.com/Women_.....1-2600.htm
very very snazzy!
here's a link to Tula hats.
http://www.tulahats.com/
Some of the styles come in a variety of sizes, you have to check the info on each style. More of the unisex and men's styles come in larger sizes, but their standard medium fits a 22" head. They seem to run larger than a lot of hats out there. Goorin has different sizes but i've yet to see one of their hats with a large brim.
Also, if you can get to a store specializing in hats you will have better luck. here in the east bay we have berkeley hats on telegraph:
http://www.berkeleyhat.com/
tons and tons of hats! i'm personally jonesing for the tula somerset hat:http://www.tulahats.com/Women_.....1-1170.htm
really sweet on! good luck, just be persistent (stubborn?) and soon all your friend's will be saying 'oh, she's just one of those lucky people who can easily wear hats!!' steph