Shepherd's huts were used 200 years ago in Britain by shepherds who followed the flocks to different parts of the countryside, as one field was left fallow to regrow and another one gets fertilized and eaten by the sheep. They had iron wheels and were not really easy to move, and don't roll down the roads today very easily. So they really don't make much sense as a model for a modern tiny home or garden office.
Or do they? It's all about the rules. If it's on wheels and under a hundred square feet it probably can go anywhere without a building permit. And furthermore, these new ones built by Güte just south of Collingwood, Ontario are really well designed and well made and too cute for words.
UPDATE: The original classic hut was covered by TreeHugger Kim earlier, in Off-grid 84 sq. ft. tiny homes are handcrafted for rustic living