One of the glittery boots needed for the school play has gone missing, and Rarity decides to play detective and figure out where it went.
When interrogating Pinkie Pie, she confesses even though Rarity knows (and reminds her) she has an alibi, but the prop turns up in the room on its own. In interrogating Trixie, the two refuse to speak to each other and have a duel of inner monologues, but Trixie finally cracks and begins to leave, but they find Spike, who took the boot. If she interrogates Applejack, the boot turns out to have been stolen by Maud, who was enamored by the gemstones on it.
- Bait-and-Switch: None of the people Rarity questions actually took the boot, and in Pinkie's case, it wasn't even stolen, just misplaced.
- Cloudcuckoolander: Pinkie Pie, as usual. She quickly cracks and admits the theft to Rarity, who has to remind Pinkie she couldn't have stolen the boot, she was at the mall getting frozen yogurt. In fact, she's still holding the yogurt she bought!
- Contrived Coincidence: In all three shorts, the boot, and/or the person who took it, just happen to be in the interrogation room.
- Deliberately Monochrome: The investigation segments are naturally in grayscale, to go along with the Film Noir atmosphere.
- The Dog Was the Mastermind: In Trixie's ending, Spike was the one who took the boot, because he wanted to see what being a dancer was like.
- Dramatic Thunder: Mocked by using a flash and thunder alongside the reveal that it's Maud Pie who took the boot... except it's Snips and Snails who are doing the special effects with a lamp and a sheet of metal.
- Failed a Spot Check: Nobody noticed one of the boots was missing until Flash points to where they both should be during rehearsal.
- Ham-to-Ham Combat: Rarity and Trixie manage a non-verbal one as they have a duel of inner monologues while using their physicality to communicate.
- Hypocritical Humor: Rarity and Trixie both speak in their heads at the end of the case, and Spike, wondering why nobody is talking out loud, asks this in his head as well.
- Imagine Spot: When Maud mentions a several-ton gemstone she knows of, Rarity imagines herself hugging it. Maud is doing the same thing.
- Nice Hat: "Detective Rarity" once again dons her fedora.
- Oh, Crap!: When Trixie sees Rarity brought her make-up with her, she realizes Rarity could spend hours doing it, and there's no way Trixie can outlast her.
- Perp Sweating: Rarity attempts this with each "witness".
- It works too well on Pinkie Pie, who immediately start sweating and is soon confessing everything, even though she did nothing wrong and Rarity knows it.
- The silent treatment doesn't work much on Trixie, however, who stays unflappable... until Rarity pulls out the make-up implements.
- Private Eye Monologue: Rarity, of course, narrate the action in this style. Unfortunately, so does Trixie, leading to a silent duel of nerves. Lampshaded by Spike at the end, who wonder why nobody's talking out loud.
- Reveal Shot: Maud Pie is revealed to be the culprit along with Dramatic Thunder... except the camera zooms out to show that Snips and Snails are causing said thunder and lightning with props.
- Rule of Funny: A cutaway from Pinkie and then back has her inexplicably holding a tub of frozen yogurt that she obviously did not have before, but that's the joke.
- Shout-Out: The short is an homage to the Rarity Investigates! episode in the main series, even having the same name.
- Splash of Color: The boot, as well as Rarity's lipstick, are still colored within the grayscale segments.