well. as a constructivist linguist I would say, it depends on the implicit message of the utterance. out of the context, taking into account the underlying power structures and the ongoing negotiation of the identities of the subjects involved in the dialog, one should be able to classify the question as some kind of speech act. I would say that the speaker is performing an illocutionary directive speech act (Austin), and the motivation/intention of the speaker can only be elucidated in each concrete case.
out of my experience in most cases the speaker is either requesting an honest answer regarding the chose of clothing or demanding approval/confirmation from the hearer.
first case scenario: the answer depends on how the clothing actually fits to the speaker.
second case scenario: "yes, baby, you are stunning. the (dress/pants/tshirt...) looks great on you!"
x. lulu


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