I think part of it (one third) isn't just the issue of finding a hat that fits nicely with your hair tucked in perfectly, its the issue of identity. If the hat isn't you then you just won't want to wear it.
Maybe it has lines on it the wrong way and you don't like how it looks in a mirror.
Maybe its just the wrong colour and nothing matches it.
Hat hunting (especially in the cold winter months) can be very tricky. You want something warm that will protect your hair from the elements, but won't scrunch up your hair and give you "hat head" when you take it off.
For many people with Afros the answer is a beret-style hat like the one below.
But what if you don't like berets? Maybe you want a cowboy hat or something different. Its all very tricky.
Which brings me to the other 3rd of this conundrum: FASHION.
Or what if you're a man and beret's just don't suit your masculine physique? (See Men's Hats.) Well then you're just kind of screwed, aren't you? You have to cut your hair to match the king of hat you want to wear.
Such is life.
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