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Rich Hobo 

a girl who is obviously from a rich family, yet insists on sporting a look that makes her seem like she lives on the street. Upon further examination, her clothes are revealed to be designer rags.
Girl 1: Oh, Jesus did you see Olivia? She looks like trash.

Girl 2: Yeah, but it's all Prada and Burberry (and all that shit)

Girl 1 : She's a rich hobo?

Girl 2: Are you fucking kidding me? She's the definition of Rich Hobo!
Rich Hobo by Cool Moe D. December 7, 2009
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Rich Hobo 

A person who can look rich and homeless at the same time. For example, Snoop Dogg and Post Malone.
Snoop Dogg and Post Malone look like Rich Hobos
Rich Hobo by Justin. Y June 19, 2020