He got all his clothes from a consignment shop after he got out of prison. You have to watch the series. The hat is supposed to be a designer piece which a widow (Diahnn Caroll) was placing on consignment, and he recognized it, tried it on, and she immediately invited him over and supplied the rest of his wardrobe, allowing him to move into her very desirable Park Ave. digs.
You have to have watched the series.
The hat is a prop that crops up again about every 2nd episode.
Boy, I did get it wrong! Thank you for catching me up!