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Here's a quote from an American animation "Trolls":

[referring to Cloud Guy]

Poppy: Branch, he's trying to help us.

Branch: I don't like the looks of him. I mean, who wears socks with no shoes?

Poppy: He seems to know what he's talking about.

Cloud Guy there is a character in the animation that looks like a cloud but certainly acts like a guy, i.e., anthropomorphic.

So it's as if you're talking about a guy who "wears socks with no shoes" and you don't like it. In this context, is it correct to say "I don't like the looks of him" instead of "I don't like the look of him"?

Is it also correct to say "I don't like his looks" instead of "I don't like his look" in the same context?

If the plural "looks" is correct in the given context, when should you use the singular "look" instead and say "I don't like the look of him." or "I don't like his look."?

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    "I don't like the looks of him" or "I don't like the looks of that" is idiom. It means that the appearance of the person or thing is suspicious, unsettling, or foreboding. The other variations wouldn't have the same meaning. This is common in AmE but I couldn't find an official reference to cite, so I'll leave this as a comment rather than an answer. – fixer1234 May 7 '17 at 2:41
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When look is used as a noun, it can mean turning the eyes toward someone or something, or the appearance of something. Here is the definition of the appearance meaning from the Oxford Dictionary:

2.0 The appearance of someone or something, especially as expressing a particular quality.
the bedraggled look of the village

2.1 looks A person's facial appearance considered aesthetically.
he had charm, good looks, and an amusing insouciance

2.2 A style or fashion.
Italian designers unveiled their latest look

Note that, in meaning 2.1, looks is used as a plural. They suggest that this meaning just relates to facial appearance, whereas in your sentence it is used to describe his general appearance- including footwear. Compared to the dictionary definition, this is a slightly wider interpretation of looks, but it is not in my opinion unusual.

Merriam-Webster also makes the distinction that the usage of the plural relates to ones physical appearance, rather than to what one wears.

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In Collins dictionary, "don't like the look[s]" is explained with both the singular and plural use.

Whether you can substitute

"I don't like the look of him" with "I don't like his look".

I would say... Maybe. Depending on the context, you could make it very clear that you find him suspicious. If no context is provided it could easily be misinterpreted as: You actually don't like his appearance.

In contrast, the idiom without context provided would most likely be understood.

Collins explains the idiom with both look and looks. And both expressions seems valid, with look being the more common option chosen.

A Google exact search for the phrase using look returns:

I don't like the look of him: 104.000.000

I don't like the look of it: 20.100.000

A Google exact search for the phrase using looks returns:

I don't like the looks of him: 520.000

I don't like the looks of it: 978.000

Apparently J.R.R Tolkien used the phrase with look in "The Hobbit".

Ultimately I think it boils down to writing style.

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