A regular feature of the Toronto Daily Star in the mid-1930s or so was portraits of young dogs and cats dressed up like humans. Here’s one from the June 22 1935 edition of the Toronto Daily Star:
And here’s one from two days later, June 24 1935:
These somewhat twee photographs and captions were the work of Harry Whittier Frees (1879-1953), a photographer based in Pennsylvania. The photos seem a bit cruel to modern eyes, as Mr. Frees got his subjects to pose using stiff costumes, pins, and forks. He only worked three months a year, as making the images was quite stressful.
Mr. Frees appears to have had a difficult life. He never married, and spent much of his adult life caring for his parents. He committed suicide in 1953 after learning that he had cancer.
NPR has an article describing his life and career in more detail.