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What does of mean in this sentence?
SHE HAD THE LOOK OF HOPELESS ANEMIA THAT DISTINGUISHES THEM FROM FULLER BLOODED SORTS.
A row of Lombardy poplars stood in front of my great-aunt Gertrude's house, on the bank of the Sheepscot River. In personal appearance my aunt was surprisingly like one of those trees. SHE HAD THE LOOK OF HOPELESS ANEMIA THAT DISTINGUISHES THEM FROM FULLER BLOODED SORTS.
OF = CHARACTERIZED BY??
Comments  
wholegrainOF = CHARACTERIZED BY??
Not exactly, but close. Anyway, I don't think it's necessary to find a paraphrase of the single word of to understand the meaning.

She had the [look / appearance] of hopeless anemia
~
She [looked / appeared] as if she were hopelessly anemic.
~
She [looked / appeared] hopeless and anemic.

CJ

P.S. Bold or italic fonts are recommended over capitalizing.
related to?
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I think it's "related to" thinking of it. Because I just read a similar sentence: She had the look of death.
Thank you.
wholegrainI think it's "related to" thinking of it.
Yes, or "associated with".

Or: that ... has.

the look of death ~ the look that death has
the look of love ~ the look that love has
the look of impatience ~ the look that impatience has

CJ
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Thank you.

Does that mean:

look related to death
look of death
look that death has
death's look

all mean the same thing?
wholegrainall mean the same thing?
Approximately, yes.

CJ