2

だけど...

冷えるんだったら スカートじゃない ほう が いい ん じゃないのか?

I just don't understand this sentence.

I'm not keen on if ん is の(?) in both cases and I assume ほう(方)simply indicates an action and there's a double negation.

"If it grows cold, a skirt is... (not?) good [to wear]...not?"

Does the character think it should or not be worn for warmth (is it better not to?) (it isn't being worn, for the record) and what about the second ではない(の)? Does it just mean "is that not right?"?

1

Yes, the second じゃない is an informal way to say something like "right?" or "don't you agree?". You can see the rest of the sentence as the actual statement, and じゃない just as a way to involve the other person. Something like "isn't it?", if you want to have a negative example.

0

Don't know how this will help your understanding but I usually read "じゃないのか?" as "Is it not?"

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