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I've stumbled across this line in a short novel and all of a sudden, everything I've learnt so far as a student in the language has gone out the window by something as simple as the "で" particle.

「美咲{みさき}のそういう冷たい顔で暑苦しい所、本当にキモいと思うけど、結構好きだよボク?」

From what I can gather, it almost feels like で should be translated as something like "yet or "but" here, but I'm not aware of any usages of "で" with this sort of nuance.

"A cold expression like that on Misaki yet[?] In a hot place, I think it's really gross but I kinda like it?"

I'm not sure, the whole first part "美咲のそういう冷たい顔で暑苦しい所" seems a mess when I try to translate it in my head and I think it's because the で is causing me confusion, so it would be great if someone could point out where I'm going wrong :)

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で on its own does not have the nuance of "but" or "yet". Here this で is simply the te-form of the copula. ~顔だ and ~顔をしている are common expressions in Japanese (see: Describing facial expression).

Basically 冷たい顔で暑苦しい (literally "being sultry (while) having a cold face") is a kind of oxymoronic expression and should be treated as such. Explicitly inserting "but" in a rhetoric expression like "bitter sweet" is awful, isn't it?

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