This site says:

Here the How…? form is sometimes associated more with positive features and the What...like? form more with neutral or negative features:

How does she look? ~ Fantastic! That outfit really suits her.

What does she look like? ~ As if she hasn't bought any new clothes in the last twenty years.

Would you think there is a distinction between "How do..look" & "What do..look like"?

  • This US English speaker doesn't really think there's much of a distinction like that. It seems like a really artificial distinction that doesn't match up with how people actually speak. I can easily imagine a conversation like "How does he look? Not good. I don't think he will survive until tomorrow." Or "What does she look like? She's a tall, attractive woman who dresses in the latest fashions." – stangdon Mar 16 '17 at 16:13

"How does X look?" is for value judgments, negative or positive. "How does she look?" "Just awful!"

"What does X look like?" is asking for a physical description, not an opinion of the overall look. "What does she look like?" "She's a tall, dark woman in a black dress."

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