A sub-term stemming from the word Vagabond (1: moving from place to place without a fixed home : wandering
2 A: of, relating to, or characteristic of a wanderer B : leading an unsettled, irresponsible, or disreputable life)
However the swagabond is an individual who is well kept and is unsuspecting to the general public as person who is effectively homeless. Similar to the couch surfer but applies to a more broader group and is specific on style and hygiene.
"Wait, that dude is homeless? He dresses so well, that dude's a Swagabond
12 step recovery jargon referring to someone new who talks about how great life is, now that they'resober. Usually meaning that the person is out of touch with reality.
The new guy seems pretty happy for a dude who has no job, no money and no family. He must be on a pink cloud.