Wow, for being a professional fashion guy, that guy had a
really poor sense of fashion. Mc had what was supposed to be considered a somewhat lame outfit, and it got turned into a
super lame outfit instead. And for some reason he uses it for the rest of the date, despite fmc not changing to her new outfit.
Gags centered around a lack of pronouns are hell to TL properly. I remember She Was Actually My Stepsister where one TL just threw up his hands, explained the bit and used the character's true pronouns rather than trying to force the joke in somehow.
Unless they can think of a really good way to translate the joke/whatever, then that is exactly how a good translator
should do it. Good translators makes extensive use of translator's notes for untranslatable parts, rather than replace it entirely with some original content that is unrelated to the source material beyond being a pun/whatever.
Though often it can be ok to lower the use of tl notes by assuming a level of familiarity on the side of the reader, such that there's no need to explain ie. "-san", "-senpai", "-degozarou", "nyan", and other common suffixes, verbal ticks, or onomatopoeia.
Still, for the thing in question - translating gender-neutral pronouns into a very gendered language - a note will be needed if you think it is used as a literary tool (and otherwise you just replace with the pronouns that match the character's sex. Or rarely, use the gender-neutral plural "they/them" for the singular subject, if it works with the sentence-flow).