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older and fashionable man (wild-looking, burly, etc.)
ちょい悪おやじのファッションだ。
It's the fashion of a playfully bad middle-aged man.
ちょい悪おやじを目指している。
I'm aiming to be a playfully bad middle-aged man.
ちょい悪おやじが人気だ。
The playfully bad middle-aged man style is popular.