If you want to get a head, get a hat.

I have a Tricorn hat that occasionally gets used for the commute to work. The amount of people that raise a smile when I walk past them makes it worth while.
 
Just LOL if you're not wearing a ten gallon hat in the supermarket and double thumb pointing at every grocery item you pick up, muttering "got you in my sights good buddy, pew pew".

e: noobs.
 
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Panama for the hot summer days. Don't wear baseball caps as I don't like logos on clothes, may look for some plain ones. Recently bought a flat cap for the winter for the first time in my life at age 47 and am slowly introducing it into my social life. Its in my jacket pocket when I go out and goes on my head for the journey home. Baby steps.
 
I carry a couple of buffs when out and about, if it's hot I wear one as a do rag to cover my head and neck, if it's cold, I wear one as a beanie, if it's super cold, I can wear one as a scarf as well.

If not needed, they fold up tiny and fit in a pocket. Multifunctional and practical :)
 
I don't think there will ever be a time in my life where I wear a hat. I just don't like having stuff on my head. Nor do I like how they look.
 
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Beanie when outside in winter on very cold days.

Floppy brimmed hat when fishing on sunny days. Waxed baseball cap when fishing on rainy days.

I like baseball caps in sunny hot weather because the peak helps shade my face when facing the sun, and if the sun is behind you can turn it 180 degrees to keep the sun off your neck.

My best hat is a foldable baseball cap. It's light and fits I'm my pocket when not wearing it:

 
Given my massive bonce it’s difficult to find hats that fit. But I do have a woollen flat cap for the winter and for summer a Panama or a baseball cap if it’s more casual.
 
Winter - beanie
Summer - I have two:
* a camo soft bush master style hat for around the garden. It has metal mesh hold buttons that stop it getting hot but has a wide but flexible rim.
* a madeira hat - which is made from straw and has a narrow rim turned up but just stops the glare.
 
Cold Weather - Beanie with a peak
Warm weather - wide brimmed cricket style hat or a cap
We do have a daft hat pub crawl event each year too which brings out some awesome millinery :cry:
 
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