Belting intentionally oversized pants?

Under what conditions does something like this work well, if ever? Can it work with a variety of styles or would you have to be going for something fairly specific like a city boy look? What makes it seem intentional rather than giving a hand-me-down vibe?
729CC823-9E85-43D5-BEF2-82B2F009F19C.jpeg
O1CN018pYmcB1yUbeOPyFaj__2206959856582_480x480.jpg
Was this page helpful?