My father used to always get in trouble back in the '40s and early '50s (he died in '53) for not wearing a hat, but he hated 'em.
I, by contrast, am very much a hat fan, especially as my forehead approaches the zenith.
Before bicycle helmets became available, I used to wear a railroad engineer's hat for cycling. I switched to this from a baseball cap after someone explained to me that a basaball cap is designed to blow off your head as you chased the fly ball, whilst the engineer's cap is designed to not blow off when you stick your head out the side window of your locomotive. I rigged a mirror to the visor, using a crocodile clip. Unless you're very new to this site, you've probably already seen my helmet, a Bell Image, featuring Igor the Eagle.
This may be the only bicycle helmet in the world that has its own Web page!
It is the most amazingly effective conversation starter, and has never brought me anything but positive comments...unless you count the time a cop said "Sieg heil!" as I rode by. I informed him that Igor was an American eagle.
I sleep in a Snap-On wool-type knit cap, pulled down to cover my eyes, but not my nose. I've become so accustomed to this that I cannot get to sleep without some sort of hat.
A reader of this page tried it, liked it, and wrote a nice testimonial.
On of my favorite hats for some years has been a basque-style beret. I've got two of 'em, one for the shop and one for home. One of 'em I bought at Mont St.Michel, t'other is a road find. I never wore a beret in France. Over there, they're mostly only worn by American tourists and hicks-from-the-sticks. They are also somewhat associated with right-wing politics and even the Vichy regime. Here in Newton, however, they're fairly cool for bearded left-liberal guys of my age--and it's very comfy.
The photo to the left shows me on stage in the 1997 Midsummer Revels
I've got two beloved baseball caps, the genuine kind without the ugly plastic adjusters; I bought the Cubs one at Wrigley Field, the Red Sox one locally. I mostly use these for driving. I also sometimes wear a black Campagnolo cycling cap which is densely covered with pins and buttons, mostly bicycle related.
When I visited Turkey, I was very taken by the cool caps worn by enlisted men. They've got short bills, and sort-of wrap-over parts that might vestigial, purely ornamental earflaps. I was able to pick up a blue (air force) one, but, alas, it's too small for me. I also own an antique collapsible silk opera hat, which was a very cool thing to wear back in the '60s as an adjunct to my hippie regalia.
I piloted a borrowed tandem away from my wedding in this hat, as you may see.
Another rarity is my "Bonnet Phrygien", the red cap of the sort worn by the insurgents during the French Revolution. This is inspired by the caps worn by freed slaves in ancient greece, and features the revolutionary red-white-and-blue cockade. Also very dear to me is the plastic Crown I got to wear in my only starring role, as King Paramount in Gilbert & Sullivan's Utopia Limited. For the winter, I've got a wonderful East German army chapka, booty of the Cold War. ($15 at an army-navy store in Harvard Square, Cambridge, Mass.) I think it looks really great on me. A recent favorite is my gen-you-whine Irish tweed cap, which also fits me very nicely and looks good. This was also a road find.
I'd really like to find a '20s style straw boater, but in the mean time this summery straw hat works for me. Other hats I dream of finding include a bowler (derby), and maybe a French military kepi... size 7 1/2. Probably my favorite hat is a dark green reproduction of a kepi worn by Irish units in the War of the Southern Rebellion. I got this from an online dealer called "The Book Guy." It is made of wool and leather, and is supposed to be quite authentic. It certainly looks it to me. I like it a lot. I'm also constantly tempted to buy a 1975-style Red Sox cap...that year, the dome part was red, with a dark blue bill. I'm a sucker for red, and think that looks much nicer than the current all blue version--that's just the same as a (ptooey!) Yankee cap with a "B" replacing the "NY." My Slavery War kepi I found by accident, while searching the Web for a French police/military kepi. I eventually found the real thing in an army-surplus store in Salem, Mass. It was just luck that I blundered into it. They only had one, but it happened to be a perfect fit. It was also marked $11.95, which might have been a mistake. A recent road find is this John Deere "gimmee" cap. It's nicer quality than your typical one-size-fits-all baseball cap, with a cloth adjustment strap and metal buckle.
On the side of the bill it says "owner's edition." I'm not a John Deere owner, but this is a very comfortable cap, and the green color goes well with my artificially red beard!
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