I'm pretty sure that Michael was referring to the time we met at Topper, and I was almost certainly wearing one of three hats - my summer straw hat, or my standard all-year felt Aussie hat, or maybe one of my tweed caps. Once I find a hat I like, I tend to wear it until it's almost embarrassingly dirty (felt hats are hard to clean, as Spooky discovered.) I have been bald for 25+ years, and I have rather pale skin prone to burning, so I consider them a necessity.
As for style, I try to find shapes that don't make my pumpkin-head look even fatter than it is. The design language of hats is surprisingly subtle. The best styles for someone depend on their head shape, hair style, tall-short-thick-thin etc. Thin-brim fedoras look like pencil erasers on my head, and wide brim western hats look like I'm doing cowboy cosplay, which definitely doesn't fit my personality. Best for me are the Aussie outback-style medium flat brims, some styles of "Panama" with medium brims, and vintage-style driving caps.
Here's some cropped photos of my everyday hats and some specialty hats that I wear for dressy or other occasions.
Picking mushrooms in my everday standard felt Aussi. My most perfect hat.
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British Tweed driving cap - another favorite, which travels with me when I fly because it squishes well. (Dinner with friends in Gdansk 7 years ago.) I have worn this hat since 1990 or so...
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My favorite straw summer hat. Getting a bit dirty after 30 years of wear.
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Comparisons - three brimmed "outback style" hats - my fave on the left, a Stetson on the right. Brim size affects the "western-ness". I have two other Stetsons that I don't wear because they are way too "cowboy", I guess due to the brim shape.
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Speaking of Aussie... when I was in Southeast Australia in 2012 for some concerts, our host gave me an authentic vintage outback hat with very wide brim. It's quite a rare treasure here in the U.S. - my standard everday outback for comparisons.
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Regarding caps, I like both of these styles. Note the differences between "drivers" on the left and "newsboy" on the right (also maybe a golfer's or caddy's traditional cap.)
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Casual and dressy "straw" (fiber, raffia or whatever.) The one on the right is one of several "Panama" shapes and the best one for my head. I purchased this one to wear at an outdoor wedding (that I was officiating) on a hot day in wine country. It looked quite dapper I think.
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