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And for hip-hop artists who live under repressive regimes throughout the world, “dropping bars” to air one’s grievances against the government can mean time behind bars or worse.

In fashion, it is considered poor form to air one’s grievances in public, let alone at a party, and directly to an editor in chief; and yet Mr. Posen, in his meteoric career since founding his company in 2001, around the time of his 21st birthday, has never allowed decorum to stand in the way of his tongue.