Applejack, even though I really dislike how Applejewel looks. AJ pretty flawlessly pointed out Rarity’s imperfections while keeping well within character. Rarity was being selfish and material, making a trashy mockery out of AJ’s lifestyle and upbringing. (I would have been far angrier with her than AJ was, but I guess that goes to say she’s the better pony out of the two of us)
As for who wore it better, they both look laughably terrible, in my opinion.
Applejack. Rarity was trying to out-Applejack Applejack, to impress Trenderhoof. Applejack was playing Rarity straight. She pulled it off well. Rarity, not so much. She couldn’t “do” Applejack by trying to outdo her.
“Simple Ways” is a great episode because it really showcases just how artificial Rarity’s persona is. She will do anything, BE anything, to get what she wants. Contrast that with Applejack, who couldn’t put on an act no matter how hard she tried.
Is this implying that Rarity’s ridiculous caricature of a farm pony is in fact Applejack’s “look.” Cause if those are the implications, I’d be a little insulted if I were AJ.
(Then again, AJ’s dress was quite exaggerated as well, just more glamorous).