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I just find utterly curious that chulada has almost opposite meanings depending on the country.

chulada. (De chulo).

  1. f. Acción indecorosa, propia de gente de mala educación o ruin condición.

    ...

  2. f. Guat. y Méx. Belleza de las personas.

I've tried to find out an evolution process for this word, but I haven't been succesful. Has somebody an idea?

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I have to say that I'm really surprised about the first definition of chulada you included, I had never heard it with that meaning... I may use chulería with that sense...

Obviously it should be correct because it's in the dicionary, but I'd only use the word chulada with the meaning of the second definition in the dictionary -which you omitted-:

Dicho o hecho gracioso con cierta soltura y desenfado.

And in this case, the meanings in Spain and in Guatemala and México seem to be much more similar, don't they?

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En el significado #1. Yo creo como dice en diccionario chulada cuando el contexto es sobre chulo aunque no es muy comun usarlo, pero puede darse el caso –  Emilio Gort Nov 17 '13 at 23:39
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I've heard the word "Chulo" refering someone as a "Pimp", so it could be used as a bad word.

But the word "Chulada" is always used to say something is really amazing or beautiful.

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