In the United Kingdom, a skipper is someone who sleeps rough -- someone who sleeps in a hedge, haystack, or bus shelter. This comes from the 1920s sense of skip meaning a barn or shed, not the more modern sense of a dumpster. It originally was used as a verb, as in 'do a skipper', but now it is primarily used as a noun referring to a homeless person, or as an insult indicating that you look unkempt.