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ちょっと乱れてる感じとか頑張って無造作に見えるような努力が伝わってくるし

Does it mean the person has a messy hair because he puts effort to look casual so it wouldn't seem like he's trying to impress?

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    Your assumption may be correct, but with only this much of a sentence fragment, even a native speaker cannot say something with confidence. Please include the full context. Without reading your interepretation, I cannot even tell this is about hair style.
    – naruto
    Jan 18 at 1:05
  • This came before その髪型かっこいいと思うよ私はこ。 but other than that there isn't much context within the story that explains what it really means, someone did call him out on his looks previously. I saw a translation that said " when it's all disheveled it looks like you're hardworking and carefree"
    – user50249
    Jan 18 at 1:24
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    Next time please keep in mind that we do not do bulk translation checks. Please always try to specify your largest concern (word, grammar point, etc). It's a rule, but practically speaking, it's simply hard to explain everything that you might have missed.
    – naruto
    Jan 18 at 2:08

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ちょっと乱れてる感じとか頑張って無造作に見えるような努力が伝わってくるし。
Seeing that slightly messy look(, for example), I can feel the effort you put to make it appear (intentionally) unkempt, you know.

  • ちょっと乱れてる感じ: a bit messy feeling/appearance
  • とか: and such; for example; for one (working also as a topic marker)
  • 頑張って無造作に見えるような努力: a hard effort to make it look unkempt/wild/rough
  • ~が伝わってくる: I can feel ~
  • し: (nonexhaustive reason marker)

Maybe とか is what threw you off? とか can work as a listing particle ("and"), but here it has replaced the topic marker (see: How is とかいた being used in this sentence?).

I still don't know if this is said as a sarcastic remark or a genuine compliment. See the previous countext which you did not provide.

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