Here's my nastiest hat.
25 years ago It started out jet black with a pretty, gold embroidered, UPS logo and the word "racing" embroidered in red, white, and blue under the logo. It even had bright gold edging around the brim and Dale Jarret's number 88 embroidered across the back in UPS brown outlined in white.
Now it is pretty much all the same uniform dirty gray color of used motor oil, dried sweat, and dirt - with a few smears of paint and silicone gasket adhesive for good measure.
It isn't too badly frayed or torn up - but that's 'cause it ain't ever been washed.
I still wear it working on the cars.