The occupation for June in this Simon Bening calendar image from the Da Costa Hours (Morgan Library MS. M.399, fol. 7v) is sheep-shearing. It’s pretty much exactly what you’d see today, though electric clippers are more common these days. Bening also depicted sheep shearing for the June calendar page in the Golf Book in a strikingly similar scene.
The positions of sheep and shearer are the same even now. A fellow in a coat and hat is leaning on a walking stick; this might be the owner or the shepherd, or even a nosey neighbor, but his clothing marks him as someone who’s more than a peasant laborer. He has his left arm in a sling; a detail which makes me wonder if it was a portrait of someone specific.
Behind the sheep and the shearers in the Da Costa Hours calendar image for June are what appears to be two fair substantial buildings on a hill; notice that at least two of the buildings have thatched roofs. Higher up on the hill, as the details images show, are a deer and a rabbit. Off to the right, below the hill, a couple, possibly courting, are seated on a bench.