I have a few dozen ball caps, a few winter ski caps filled with gloves, and an Indiana Jones hat that my boys bought me once on Fathers Day. I have my father’s tweed walking hat, but that’s a keep-sake and not for wearing.
I am surprised by the number of hats I own. A Cast-Iron Bowler (it’s a black bowler or derby, that’s just what they’re called), a straw trilby, a sable Ushanka (Russian hat), a black Top Hat, a collapsible Stovepipe hat (mainly for laughs), and a whole bunch of baseball caps, knit caps (including one from Peru). All I ever where outside of a costume-y occasion is the Bowler or the baseball caps.
about 15 ish that are not baseball caps, or knitted beanies.
I have about 10 hats probably, about 5 baseball hats and 5 beanie hats. I like to wear silly hats.
I figured this for a hat wearing crowd. Glad to know I’m in good company. Keep it coming.
I only have one hat that I wear with any regularity. It is a Real Deal Brazil hat that my wife gave me as a gift. She found them online and bought me one before they started being seen on TV and in movies.
I also have a Panama Jack straw hat and an even older Mickey Mouse black straw hat that was bought at Disney World several years ago.
"Oh, this is the worst looking hat I ever saw. What, when you buy a hat like this I bet you get a free bowl of soup, huh?.. Oh, it looks good on you though. " 
I have a large number of baseball caps. I haven’t counted them so I don’t really know how many I have.
Broad brimmed cotton bush hat for sun protection, and a short billed cap I keep in the car for when I have the top down (stops my hair getting too messed up).
There’s two closet shelves on two walls to hold my hats, most of them in stacks. After 30 years of collecting there’s a wide variety of color combinations, hunting camo styles and products/places for most any casual situation. Usually when I get home from work I put on jeans, sandals and a hat. When I get up at 4:00 on the weekend I put on shorts, a hat and fire up the smoker. If I’ve got to mow in the rain… straw cowboy hat. When packing for a trip I’ll pick out about four that match the clothes I’m going to wear. There’s a good head of hair up there, I just like hats.
I only own one. I don’t really own hats, and I don’t have a delicate face for those fascinators that I love so. But I do own a lovely wide-brimmed hat, beaded, for sunny days.
I had a friend like that (named Annie as well, oddly enough). Already pretty, but adorable with a hat on. What’s funny is she said no one ever mentioned it until I did, and suddenly people were stopping her to say how cute her hats were (I think she ramped up wearing them after I mentioned it).
I’ve got 3 baseball caps - one souvenir cap a friend brough back from a trip, two gifted from BMW when I made a trip to their factory in Greenville. I’ve got two fedoras, one gray felt with black band, one black felt with gray, for business/formal wear. I don’t count my motorcycle helmets as hats - more sports equipment.
700
All Fedoras, cause I’m just such a hipster
…
Actually, got an Indiana Jones looking leather hat (my go to bad weather hat), a couple of cowboy hats (1 straw, 1 felt), and maybe 15 - 20 ball caps, some fitted, most not. Didn’t pay for a single one of those and I tend to wear those to work in. Knitted caps aren’t a “hat” in my pov, but I wear them as the need arises.
I own zero hats. If it is super-cold I would wear a hood, scarf or earmuffs (or all three), but hats don’t look good on me.
Many hats… cowboy hats, both felt and straw, a fedora, too many ball caps to count, a couple of knit hats, head ‘rags’ for motorcylce riding, I wear them underneath a beanie-type helmet. 