Basho knew his classics and used that knowledge frequently in his haiku. The following haiku is, as Jane Reichhold says, a pseudo-science haiku.
Let us look at the haiku on the Bush warbler.
uguisu no kasa otoshi taru tsubaki kana
a bush warbler
has dropped his hat
|Taiwan Bush Warbler|
In old (classic) poems (e.g. waka) there was a phrase about the bush warbler (looking similar to our cuckoo) stitching a hat from plum blossoms. Basho changed the hat to a camellia and had the bird dropping it - which was much more natural than stitching. If birds wore hats the camellia would be the right size and shape.
Maybe you can visualize the picture of the bush warbler wearing a camellia for a hat. It looks like a cartoon I think, but why not.
Humans wear hats so why shouldn't birds and animals don't wear them.
Maybe you lost your hat in a storm or something, so also the bush warbler could lose his hat in the storm or dropping it.
a gust of wind
a hat tolls around and around -
A haiku with a smile? I think so ... maybe a senryu?