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Yet if the style has a horizontal focus (such as a blunt bob with curly hair) the face looks wider and heavier. And if the hair is cut too short, the cut is out of proportion to the rest of the figure, and the face and head look oversized because the hair looks “too small”. So, to answer the question “will short hair make you look skinny. Medium length hair is appropriate for those people who like their hair short, but not too short, because it doesn’t go past the shoulders.