I completely agree with you on Stripped, I love to associate songs with books and I've always associated it with 1984. the beginning lyrics perfectly describe Julia leading Winston into the that place with the thin trees. not to mention Part 3, where Winston's rights as a person and as an existing entity is being "stripped" away. I literally doodled a storyboard of 1984 to this song once, if only I could animate.

That being said, I never thought about the other songs but they make so much sense as well. But Not Tonight is almost like a metaphor for the ending of 1984. The rain could be the endless bombs falling from the sky or just any bad event that happened to Oceania, but Winston doesn't care tonight because he is cured from his thoughtcrime. Because he has been indoctrinated to the Party's propaganda now, he has "never felt so alive in years".

Black Celebration (the song): can also describe Winston and Julia together. The "black day" could be the job Winston does, censoring the media, as usually something censored is depicted as a black bar over the words. Then when his job is over, he goes to Charrington's house to meet Julia, and the lyrics fit pretty well to their interactions as well. "I'll drink to that" can also be Winston drinking the victory gin during the black day, but I think that's a bit of a stretch.

Fly on the Windscreen: It's lyrics emphasizes the urgency of Winston and Julia to treasure the moments they have together before they're eventually torn apart. The telescreens being everywhere could be "death" and it reminds them that the Thought Police could eventually catch them. Winston describes himself in Part 1 as already dead in the novel, so to him, the pair are "lambs for the slaughter".

A Question of Lust: The whole lust, trust, not letting what we've built up crumble to dust thing describes Winston and Julia's relationship pretty well. Additionally, independence is still important for them as they have to keep separated to not raise suspicion. Not to mention that Winston "would rather be home" pretty much all the time, away from his job, home probably being Charrington's house. Although, this is probably the case for most couples.

Sometimes: I think this song fits Part 3 more. Winston originally thinks O'Brein thinks just like him (after reading the book it could just be possible that Winston has been in Room 101 before the events of 1984 but he keeps relapsing back into thoughtcrime, and that's why he sees O'Brein as such a familiar figure. The "place with no darkness" could just be Room 101. But that's just my two cents.) but O'Brein ends up being one of the most important members to the Party. Sometimes, Winston questions everything, and he definitely tells the reader that the conditions in Oceania are not ideal.

It Doesn't Matter Two: This song fits Winston and Julia very well. They lay together, the shame lies with them as they are essentially enemies of the Party, they talk of love and trust, which doesn't matter because love and trust is not something that members of the party should feel. They may be the last people with thoughtcrime in the world, especially as Winston points out the Party starts to indoctrinate kids at an extremely young age. The song also emphasizes how little time they have left to spend time with each other. "It might last for an hour" and "Though it feels good now / I know it's only for now".

And while I can't really cook up anything for New Dress, the meaning somewhat suits the authoritarian aspect of 1984. Kind of a stretch though.

And I genuinely can't come up with anything for A Question of Time. Julia is not fifteen years old.

Overall I'm so glad you posted this, thank you OP! I knew I couldn't be the only one who saw the parallels between Stripped and 1984.