I definitely have been both to the office and on holidays with self-mended clothes. Especially tears in my favourite shorts I repaired perhaps ten times before giving up on the brittle fabric. I never was worried of stigma of clearly mended clothes; I rather was quite proud of my bohemian clothing.

Maybe it helps that we work in software engineering, so it's quite clear to my colleagues that we could buy a new pair of shorts for each and every day? Or maybe it's because of increase in environmental concerns especially with younger urban people? I can't honestly say, as it never occurred to me that it could convey a negative message.