Avoid confrontation, not people. Plus, a manager at a company presumably has money to buy a couple of sweaters, even if at Goodwill or equivalent.

I'd have to agree that it's necessary to view the professional sphere in terms of investment and investment is not only financial it's also effort and agency

If you're a professional you ought to have some sort of professional persona that's not so directly tied to your 35 year mortgage

If all your money is tied up in interest payments to where you can't hardly afford a stitch of clothing what fault of it is mine who manages my money differently do I seriously have to see you wearing the same tired old outfit every day for a week and you're in a position to affect my career to boot?

You have no idea what people have going on though. There are so many reasons someone could be short on money that would be understandable if you knew. you simply can't make that judgement easily.