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For すっきり, Jisho gives six possible translations that don't seem to have much common ground, so I have a hard time forming a general idea of what the word means, or knowing which meaning to pick when seeing the word in the real world. Can somebody help?

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    For words like these (i.e. ones that don't perfectly map to a single English word), I've found that デジタル大辞泉 usually gives a clearer picture of its meaning. It looks like there's only 4 distinct usages of すっきり, and 3, 4, and 5 all fall under #3 on 大辞泉. – Ataraxia Jun 19 '17 at 2:18
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I think it depends on context what you want to say...

Take a look on examples:

うっとうしい梅雨期に、すっきりしない話で恐縮ですが、少しの間お付き合いください。
I'm ashamed to tell such a muddled story in this dreary, rainy season, but please bear with me for a while.

まさかオレがごねずにすっきり起きると思っていなかったに違いない。
Certainly she wouldn't have dreamt that I would get up promptly without grumbling.

コートを探してます。背が低いので、丈は短めで、なるべくすっきりしたデザインのものを。
I'm looking for a coat. I'm short so the length should be on the short side, and as refined a design as possible.

それからすっきりきれいにしてくれ。
Then clean it really well.

  • Yeah, I saw the examples at Jisho and found them helpful, but I still feel like I can't tell from context which meaning applies. – python dude Jun 18 '17 at 17:20
  • Good judgment comes from experience, and experience comes from bad judgment :) – Yeheshuah Jun 18 '17 at 22:10
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Based on the デジタル大辞泉 link provided by Ataraxia and the Jisho entry, here's my attempt to answer my own question:

The general meaning of すっきり is something like "a state where all bad/unnecessary/superfluous/etc. things have been removed". Specifically, it can mean one of the following, depending on context:

  1. feeling refreshed; feeling fine; feeling clear-headed​ - with respect to one's head, feelings, mood, etc.

一杯のコーヒーを飲んだら頭がすっきりした。
A cup of coffee cleared my head.

  1. clearly; plainly; distinctly - e.g. sentence, article, writing style

「すっきり(と)した文章」
a clear writing style

  1. shapely; neatly; refinedly​ - e.g. clothes, posture

コートを探してます。背が低いので、丈は短めで、なるべくすっきりしたデザインのものを。
I'm looking for a coat. I'm short so the length should be on the short side, and as refined a design as possible.

  1. completely; thoroughly - reaching a state where nothing remains

それからすっきりきれいにしてくれ。
Then clean it really well.

  1. not at all (with negative sentence); not even slightly​ - e.g. "I don't know him at all". Basically, the opposite of #4.

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