This MOSTLY seems legit. I say mostly seeing that I would imagine that Rarity would be the one wearing the cut-up jeans and Applejack would be the one wearing the skirt. I say this given Applejack actually has canon precedent for not liking cut up or torn clothing. I also say this because Applejack looks damn fine in a skirt.
Thank you. Now I have pictures in my head. The AJ is working every day on extra jobs in addition to her work on the farm to save money for the dates with Rarity. But through some misfortune she loses the money. And Rarity simply appreciates the effort as such, bends forward and…
R: “B-But!”
Applejack: “Ya got a dozen of thoses. AND you got more money than Ah.”
Rarity: “But Darling I want to be treated like a princess.”
Applejack: “And Ah don´t wanna be treated as a piggy bank.”
Edited