Throughout most of the story, Mitty is driving around town with his wife, then he drops her off at the hairdresser while he runs some errands. He first gets scolded at by his wife for driving too fast and then gets yelled by another driver while stalling at a green light. He has trouble parking, and then forgets just what it was he was supposed to pick up at the grocer's while his wife gets her hair "done." In his daydreams, however, Mitty finds himself dominating difficult situations in more exotic settings - in an icebreaker up near the pole, in an emergency surgical unit, in a courtroom, and finally before a firing squad. The contrast between Mitty's real life and that of his imagination is of course the humour of the story.
James Thurber was a popular American humorist during the 1950s, and one of his favorite subjects dealt with stereotype sex roles in marriage.
There is a contrast of settings between the boring humdrum suburban existence which Mitty has and his fantastical hero exploits. In reality Mitty is driving his wife to town, then waiting around for her whilst completing the menial tasks he has been set to do:
''Remember to get those overshoes while I'm having my hair done,"
We get the feeling that this is the sum total of his excitement.
The second setting is as wide as Mitty's imagination which ranges from the depths of a hurricane to the warring skies; the tense operating theatre and the dramatic courtroom. One of the most engaging aspects of the story is facilitated by this distinction in settings.
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Of course, Walter's fantasies take us elsewhere, but we'll get to that in a minute. Waterbury is a pretty big city in Connecticut. Though Thurber never mentions the state, just the city, we can take a pretty solid guess that he's talking about the only major Waterbury close to the Tri-state area. Also, a newsboy goes by shouting about the Waterbury Trial, which pretty definitively refers to the Waterbury Trial of 1938, which took place in CT.
OK, enough geography. The real-life setting of this story is pretty mundane: a hairdresser, a parking lot, a hotel lobby, a drugstore – all everyday elements of any town or city. The banality or dullness of these locations reflects the dullness of Walter's everyday life. This is greatly contrasted with the settings of Walter's fantasies: a "Navy hydroplane" in a storm, an operating room, a courtroom, a dugout, a wall before a firing squad. These settings are dramatic, exciting, and out of the ordinary.