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In principle we can use:

Он выглядит как дурак; дураком

or

Он выглядит хорошо, хорошим, как хороший X

Which structure is best, or how do they differ in meaning?

I also read this in Толковый словарь Ушакова:

ВЫ́ГЛЯДЕТЬ2, всё более входящий в употребление германизм - букв. перевод нем. aussehen.
(разг.). Иметь какой-нибудь вид, производить какое-нибудь впечатление своим видом.

После болезни он хорошо выглядит.
Этот дом выглядит совсем новым.

Does that mean this verb only recently took on the meaning of "to look like"?

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Which structure is the best or how do they differ in meaning? Does that mean that the word only recently took that meaning?

The verb выглядеть originally meant to watch and see secretly where something is or what is being done. It is perfective and transitive. This meaning is preserved in modern Russian.

В толпе он выглядел своего знакомого.

The verb выглядеть in the meaning to look like was first mentioned in 1830 used by German people living in St.Petersburg. It was borrowed from German and used as a calque.(Драганов П.Д. О германизме "выглядит" в русском языке.) The usage was considered "abnormal " by some linguists (Я.К. Грот) because the verb "aussehen" was imperfective. It becomes a norm in the 20th century. In its new meaning the verb is followed by a noun and an adjective in the instrumental case, an adjective or a noun (instr. case), a comparative or an adverb. Adverbs are used as often as adjectives (full form ).

Здания выглядят неопрятными. Каким чучелом ты выглядишь. Я выгляжу моложе. Вы хорошо выглядите.

Апресян Ю.Д. explains difference in usage. Adverbs give general impression of the object.

Ты так молодо выглядишь.

Adjectives describe and add a quality to the object.

Ты сегодня выглядишь молодым и свежим.

But it's not as easy as that. Он выглядел совсем больным. But you can't use an adverb "больно". Why? Because the meaning of the verb is "to look like" and "painfully " doesn't describe a person. Adverbs and adjectives aren't always interchangeable.

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  • "Вы-": always means completion of some process (like in "выпроводить", "выбросить", "вырезать"), and I've never thought that "выглядеть" is a special case. If I remember it right, "aus-" means outward motion in German.
    – polkovnikov.ph
    Commented Aug 1, 2016 at 17:52
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It seems that usage of "выглядеть" depends on what part of speech it needs to be conjoined with.

1. Выглядеть + как + Noun phrase in nominative case

The expression is used to show that something/someone looks similar to something else.

выглядит как королева - looks like a queen

выглядела как английская королева - looked like an English queen

выглядит как новый - looks like new (the noun is dropped)

2. Выглядеть + Noun phrase in nominative case

This form is used in questions with "как", or in statements with "так." In the latter case it simply states the facts. It is the only use case which does not use similarities.

Как выглядит траектория? - How does trajectory look like?

Так выглядит спутниковая антенна. - This is how satellite antenna looks like.

3. Выглядеть + Noun phrase in instrumental case / Noun phrase in instrumental case + Выглядеть

Similar to the first case this expression is used to show that something looks like something else. There is no difference in meaning between the first case and this one.

выглядит новобранцем - looks like a rookie

выглядит смешной пародией - looks like a funny parody

выглядела бледной и блёклой - looked pale and dull (the noun is dropped)

Островком роста выглядит страхование имущества. - Property insurance looks like an island of growth (the noun phrase in instrumental case can precede the verb)

4. Выглядеть + adverbial phrase

The expression is used to show similarity. Just like the first and the third cases.

выглядит странно и неубедительно - looks strange and unconvincing

Он пытается выглядеть как можно умнее - He tries to look as smart as possible (adverbial phrase uses the word "как")

Моей дочке 13, но она выглядит на 15 лет. - My daughter is 13, but she looks as if she were 15

In short, the form that needs to be used is dictated by what part(s) of speech is used in the rest of the phrase.

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"Выглядеть" + Adverb is always without "как", in singular instrumental case, so is "Выглядеть" + Adjective.

"Выглядеть" + Noun doesn't really change meaning at all depending on which construction do you use, both are totally OK.

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  • but we can't say—он выглядит больно. I feel like this is a similar to case yo English where one can say "He looks bad" and bad is both and adverb and an adjective. Maybe for some common adjectives Russians have just become accustomed to "incorrect usage"?
    – VCH250
    Commented Jul 26, 2016 at 21:15
  • Why we can'say? We can (with only a small correction - он выглядит больнЫМ)
    – ddbug
    Commented Jul 26, 2016 at 21:23
  • 1
    And there are even more variants: "он выглядит НА миллион долларов"
    – ddbug
    Commented Jul 26, 2016 at 21:26
  • 2
    That's another case творительный and not an adverb. хорошо/ плохо итд are adverbs.
    – VCH250
    Commented Jul 26, 2016 at 21:54
  • @VCH250 Maybe for some common adjectives Russians have just become accustomed to "incorrect usage"? You seem to mix'em up. "бОльно" is an adverb ("painfully"). (Short neuter) adjective is "больнО". Technically one may say "он выглядит больнО", but it sounds so-o weird...
    – Matt
    Commented Jul 27, 2016 at 14:34

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