I have an inordinate fondness of hats and have tried lots and lots of types 
while bicycling.  Here are some fav's:

+2 on tilly brimmed hats; cotton, oilcloth, or wool.  Both Erin and I love 
them. The curve of the brim from back to front is good with wind and can be 
coupled with the chin strap on the cotton and oilskin models.  the aussie 
style snap-up sides can be helpful.  Also, slip a business card and a 
couple bills in the crown pocket. MAKE SURE you try it on first; the tilly 
sizing is sometimes whacky and they tend to run small.

+1 on panama but be sure that it fits well.  best with a leather sweatband. 
Can blow off in strong wind/downhill.  Hold on.

others with brims/bills:
*bowlers are surprisingly good for cooler riding.  Harder to find; if you 
find a good one with a leather sweatband that fits. snap it up.  Plus they 
are totally dapper.
*Gorin caps, if you find a model you like, have worked well for both Erin 
and me—but they discontinue styles so quickly that if you like it, get it.
*Stormy Kromers are really quite good and now come in lots of fabrics and 
colors.  Has ear protection that can be deployed.
*radar o'reilly style knit caps are great for colder weather and can drop 
over your ears
*and the many bike-specific caps of course

haberdasheringly yours,
RCW

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