The short follows the adventures of Winston, an imaginative little boy, and his best friend Molly as they learn to use their potties and become big kids. After the short, doctors answer parents' questions of the subject of toilet-training.
Winston's Potty Chair provides examples of:
- Acting Out a Daydream: When Winston imagines the people around him wearing diapers, he notes to himself, "That's better" (meaning they look better in their normal clothes). Molly asks him what he means, but he brushes it off.
- Amazing Technicolor Population: The stereotypical Native Americans Winston imagines have blue skin.
- Barbie Doll Anatomy: Winston and Molly are drawn without visible genitalia when they are shown using their potties.
- Best Friend Manual: After the short ends, the VHS has an interview with Dr. Dan and Dr. Nelson, who give give potty-training tips to parents.
- Crashing Dreams:
- At the beginning, Winston dreams that he gets splashed with water, then he wakes up and finds he has wet his diaper.
- When Tony tells Winston that his potty is not a hat, Winston imagines one of the men in his daydream saying the words in Tony's voice.
- When Winston is imagining he's in the jungle, he imagines falling into a puddle, and then finds that he has wet his pants.
- The Diaper Change: Early in this short, Winston's mom changes Winston's diaper after Winston wakes up from a dream he has where he gets splashed by a wave at the beach. It is at this point that Winston asks his mom if he will always have to wear diapers. His mom assures him that when he's a big boy, he'll use the toilet just like his parents and his older brother, Tony.
- Goo Goo Getup: When Winston is thinking about how he won't always have to wear diapers, he imagines everyone around him wearing diapers. He decides that they look better without them.
- Go-to-Sleep Ending: This short ends with Winston and Molly asleep in their beds, satisfied that they no longer have to wear diapers.
- Hollywood Natives: At one point, Winston imagines two men who live in the jungle and wear headdresses, warpaint, and loincloths. They also speak primitively and want to make him their chief because he's wearing his potty as a hat.
- Inner Thoughts, Outsider Puzzlement: When Winston says, "That's better" after concluding that the adults look better without (imaginary) diapers on, Molly is confused.
- Irritation Nightmare: At the beginning of this short, Winston dreams about being at the beach and water going into his diaper. He then wakes up to find that he has wet his diaper.
- Kiddy Coveralls: The titular Winston is a young toddler who wears a pair of light blue overalls with his white shirt. He is a very imaginative toddler who prior to finding out what his potty chair is used for, imagines it as many different things, such as a car seat, a jet ski, and a saddle. He has no trouble with undoing his overalls whenever he tries to use his potty.
- Kids Love Dinosaurs: At one point, Winston has an Imagine Spot where he is in a prehistoric forest when he reads a book about dinosaurs. This ultimately leads to him having a potty accident, and when his dad sees him, he says, "Winston, that must be a good book! You forgot to go to the potty!"
- Leitmotif: The short has a recurring tune that shows up when Winston first discovers his potty, then again when his dad shows up, then it plays on the radio, then it plays again at the end. It doesn't seem to signify anything; it's just the cartoon's theme.
- Mistaken for Toilet: Inverted when Winston mistakes a training toilet for a hat (to the point of having an Imagine Spot about a tribe declaring him as their chief because of this supposed headgear) and then wonders if it's a saddle.
- Mistakes Are Not the End of the World: Winston feels ashamed of himself when he has a potty accident while reading a book about dinosaurs. His dad assures him that he's a big boy and that he'll use the potty next time.
- Mr. Imagination: Winston is a very imaginative little boy. When he tries wearing his potty on his head, he imagines that he's the chief of a tribe, and when Tony tells him he's supposed to sit on his potty, Winston imagines that his potty is a car seat, jet ski, and saddle. He also imagines that he's in a prehistoric forest when he reads a book about dinosaurs.
- Potty Dance: Winston does this as he listens to some music on the radio. His mom asks him if he is just dancing or if he has to use the potty. Winston tells her, "Potty!", and she tells him to hurry and use the potty before he has an accident.
- Potty Emergency: Happens three times:
- The first one happens to Tony when Winston first tries to use his potty. Tony runs right past Winston and his dad so that he can use the toilet.
- The second one happens to Molly when she and her parents go on a long drive to the beach. Because there's no potty in her parents' car, her parents have to stop at a service station so she can use the toilet there.
- The third one happens to Winston as he is dancing to some music playing on the radio. His mom sees this and asks him if either he needs to use the potty or is just dancing. When he tells her, "Potty!", she tells him to hurry and use the potty before he has an accident, and Winston makes it to the toilet in time.
- Potty Failure: Winston has an accident when he is distracted with reading a book about dinosaurs.
- Redhead In Green: Molly is a red-haired girl who wears a green dress.
- Toilet Training Plot: This short focuses on Winston and Molly learning to use their potties.
- Unnamed Parent: Winston and Molly's parents are not named.
- Unreliable Narrator: Not usually, but at one point the narrator says that Winston is visiting the dinosaurs, when really he's only imagining that he is.
- Vocal Dissonance: When Tony tells Winston that the potty is not a hat, Winston imagines the words coming out of the mouth of one of the imaginary stereotypical Native Americans, so we see a grown man talking in a little-boy voice.
- You No Take Candle: The Hollywood natives that Winston imagines speak in primitive grammar, like "You wear hat of great chief".
