Bass was ultimately convinced to dress like a hipster for Nightmare Night.
The conversation was something like this:
Bass: "Why do I have to dress like a Hipster, Midsy?"
Midsy: "Because it'll be ironic!"
Bass: "How?"
Treble: "Because you'd be dressing like a hipster for Nightmare Night before being a hipster for Nightmare Night becomes cool!"
*The two mares burst into laughter.*
Bass: "Dear Celestia, help me."
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