Some of these short tales really defy analysis, either because they are merely fragments, or they are solely meant for amusement and not for deeper engagement.
I think that this story is one of the latter. It concerns a sallow piano tuner whose boots seem to have been given to the wrong man. He goes chasing after the boots, a quest that leads to him being pelted with another man’s boots, and assaulted in other ways as well.
It’s all rather absurd but also grim, given his poverty and neediness. Chekhov’s intention seems to be lighthearted, but the piano tuner’s suffering doesn’t strike me as terribly funny.
If, on the other hand, Chekhov is up to something more serious, I don’t know what his point might be.
READ THIS? READ THAT!
Not a few of Chekhov’s attempts at humor involve the suffering of the powerless. Given the rapturous attention his short stories received–publishers tripping over themselves to buy his tales, a rocket-like rise to the top publications, encomia from the greatest writers of his age, a Pushkin Prize at the age of 28–I have to assume that this form of humor was widely enjoyed by Russian readers of the day. And not just any readers, either: As I’ve mentioned before, Tolstoy thought Chekhov’s genius was his humor. Reading the stories out loud, Tolstoy supposedly would become so convulsed with laughter that he couldn’t go on.
The cruel humor hasn’t aged well, but it’s an unavoidable part of Chekhov’s catalog. Readers focusing on the “core” Chekhov works avoid a lot of the super-short humor pieces that Constance Garnett didn’t include in her 13 volume translations. (You can see some of these in a short story collection, “The Undiscovered Chekhov,” and find links to others at “Prospero’s Isle,” a website with a wealth of information on Chekhov’s stories.)
A story with some of the same problems as “Boots” is “Oh! the Public,” in which a working man suffers various slings and arrows just getting his job done.
A Chekhov Circus 