down-at-the-heels

Having a worn out, shabby, or cheap appearance, as due to poverty or overuse. A lot of so-called hipsters try to affect a down-at-the-heels look by wearing second-hand clothing. John has been looking increasingly down-at-the-heels ever since he lost his job last year. Judging by the down-at-the-heels office space they're renting, I doubt the company is doing well.

down at the heels

Needy and therefore shabby. The expression alludes to the worn-out heels of shoes needing repair, and also to holes in one’s socks. Indeed, one of the earliest references in print is to the latter: “Go with their hose out at heles” (Thomas Wilson, The Arte of Rhetorique, 1588). The expression was common by 1700 and well worn enough to be a cliché by 1800.