I am using an easy-to-read VN to get some grammar experience. The following sentence has been troubling me for about half an hour now:
The topic of 着る is 制服 if that will help understand it better.
I have no problem understanding the first clause「生徒会に入ったらー」: "When (you) join the student council..."
My first doubt comes with the 「どうしても」, does it mean something like "by all means"? However, the biggest problem I have is wrapping my mind around this (triple negative?): 「着なきゃだめなの?」
So here's what I know: 「なきゃ」 is casual for「なければ」 and together with 「だめ」 it would mean "Gotta wear (uniform)" or less casual "Must wear (uniform)". However, since it's 「だめな(い)」 I got really confused. Does 「着なきゃだめな」 altogether mean "Must not wear (uniform)"?
I am sorry if the explanation is messy, but I tried to write down my thought process.
At some point I also became uncertain whether the topic is 制服 due to the を particle in this sentence (I expected 「に」particle after 「こっち」 "here").
Please point me in the right direction and if it isn't too much, an idiomatically correct translation would also be much appreciated as I feel it would help me figure out the X by knowing Y.