____ (slouchy style of purse named after a drift who rides the rails)

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Possible Answers: Hobo.

Last seen on: Daily Celebrity Crossword – 3/2/18 Sports Fan

Random information on the term “Hobo”:

Jack Black (1871 – presumably 1932) was a late-19th-century/early-20th-century hobo and professional burglar, author, and librarian for The San Francisco Call. Born in 1871 near Vancouver, British Columbia, Canada, he was raised from infancy in the U.S. state of Missouri. He wrote You Can’t Win (Macmillan, 1926) a memoir or sketched autobiography describing his days on the road and life as an outlaw. Black’s book was written as an anti-crime book urging criminals to go straight, but it is also his statement of belief in the futility of prisons and the criminal justice system, hence the title of the book. Jack Black was writing from experience, having spent thirty years (fifteen of which were spent in various prisons) as a traveling criminal and offers tales of being a cross-country stick-up man, home burglar, petty thief, and opium fiend. He gained fame through association with William S. Burroughs and his writings had a profound effect on the writings and lives of all the Beat Generation.

Hobo on Wikipedia