Wind and hair are certainly a troublesome combination and I guess when and where one has trouble with the wind depend on where in the world one lives. In Texas, with the changing of the seasons, fall and spring are pretty windy times of year - although Texas has a lot of wind much of the year - and wind thus is a relatively plentiful and relatively dependable renewable resource here (I asked a smart assistant the other day what the average November windspeed was in San Antonio and 9 mph, plus or minus a few tenths of a mph, came up as the average November windspeed here).
Something that works for me, but maybe not everyone’s style, is a pullover cap. It shields my ears and prevents them from flapping the breeze (today was 20 mph winds, gusting to 30 mph). And since when I’m out walking, I’m ~entirely listening to streamed sound (and walking facing oncoming traffic to make up for reduced hearing), the sound muffling/hair-ear lobe restraining effect works pretty well for me. I think it’s just about impossible to have open mics, loose hair, and 30 mph wind gusts and get the HA’s to subtract all the wind/hair/ear lobe/jacket collar, etc., vibrations out. With the head covering (just as with Ear Gear), enough sound can make it through the fabric that if I turn on my external mics (and stop streaming), I can still carry on a conversation with my wife while walking even it it’s fairly windy (she doesn’t wear HA’s).
Motorcycles, cars gunning their engines on a nearby major highway, helicopters overhead from a big medical center complex a few miles away, military and commercial aircraft overhead from several military bases and San Antonio’s main airport, large dogs barking loudly at anyone walking by on the street usually make wind a lesser concern. (and then there’re the crickets in summer!!!).