While there may be those who prefer the look of relatively short to short hair with fedoras, like anything else it's simply a matter of taste.
The biggest issue caused by longer hair is that it tends to require a larger hat size. Some here have commented about the sometimes significant change in how their hats fit after a haircut.
As a kid, I started wearing hats in the 1960s, and I had long, bushy hair then. I think the ascendency of long hair had only a very little to do with the diminution of men wearing hats, and it certainly did not effect me whatsoever.
My hair, fortunately still fully intact and thick, is much shorter these days, and I still wear hats.
Hair length and hats have practically nothing to do with one another.
Personally, I had to go to a shorter cut because my hair style was affected by my hats. I wore a simple side-part and whenever I put my hat on, it would always smash my hair down. I think a lot of it depends on your hair style and length.
A few years back I had short hair when I started to wear hats. I've since let it grow, and it is true that it affects the hat size. My lids are noticeably more snug now that I've got my flowing locks.
Some people like the look, others aren't keen on it. Johnny Depp is a well-known hat wearer, and up until recently he had rather long hair.
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