#crying meme

As you already know, the story is set in late-May 1988.

The reason she's dressed like this despite her dislike for feminine wear is because DIO has given her, Mariah, and Midler a mission to infiltrate a Yakuza gathering in Tokyo, the problem however is that the place is heavily guarded and don't allow outsiders except the entertainment inside, which in turn forces them to get creative, even if it means embarrassing her.

Fast forward and now we see Medea dressed like a Maiko, the apprentice Geisha/Geiko of Kyoto(or Hangyoku in Tokyo) who start their artistic training from ages 15 to 20. Being 18 years old at the time, she's at the right age to wear the apprentice garb.

The dresser working at the Kimono rental shop asked her she feels beautiful (or "Bonita" in this case), Medea hates it obviously but lies and says she feels beautiful to spare her feelings.

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I'd imagine that Medea would look back on this years later during Part 4 and realizes that she actually likes outfit she wore, she just hates the idea of being seen in it in front of men, especially DIO's men.

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