I am still wearing USMC issue Boonie hats. I got used to them in my time in service and I still like them. We were issued them in the 70s. Back in the 80s I bought 3 green ones at a PX for about $2.50 each, and later I got 2 tan ones (after the Marines stopped using all Green Camo in the 1st gulf war.)
Not as stylish as many other field hats but rugged and well made. And back then they were very inexpensive. For cold weather I wear “bomber caps” from REI and when they were in business A-16 from San Diego.
But for most of the year the old “Boonie covers” are still my pick.
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Bobonli: The newer model OR Seattle Somreros have a slightly broader and more stiffened brim. My first was an older (purple and black) one I found at a thrift store for $5 — liked it but had the same problem you report with floppiness in wind. Saw a newer one maybe 10 years ago and got it because the brim felt stiffer and looked wider — both true when I compared the two. Have 3 of tge newer sombreros now (donated the floppy one back to Goodwill) , an unlined one for warm weather and two of the light fleeced lines ones for cooler days (had bought the second for a friend who gave it back a year later saying it did not fit,).
The ORs are my usual paddling hat but I have found a couple of hot weather alternatives that are cooler due to lighter fabric and ventilated crowns. One is a an older model Travelsmith that has a bug headnet that rolls up and tucks under the back sweatband. Really handy on river and lake paddles during bug season. Recently picked up a very light Mission brand boonie “cooling” hat (same basic wide brimmed flat top style) for $25 while I was waiting in line at Home Depot. Made of that fabric that you dunk and wring out and it has a cooling effect. Well made for a cheapo, nice thick soft chin cord with lock, locking bungee around the crown to adjust size, sweatband is soft and stretchy, crown sides fully ventilated, foam stiffened brim that floats. Bought it for heavy yard work during this humid heat spell and it’s been great for that so I am taking it on the next paddle. Barely ferl I have it on and tge sweatband is super effective. There are bins of them in the front aisle of every Home Depot at the moment but I see they are also on line (same price).
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