Man those jus' start wearin' comfortable at that stage! I have jeans with holes in the knees that look like I was moto racing, jeans with crotch holes (good air circulation is Really Important), throw in grease stains, paint (both house & rattle can) & like you said; fancy clothes don't mean a damn thing!
I buy Walmart Levis at about $16.98+taxes but I have Rustlers & Wranglers that seem to last the longest if not ripped on anything.
Fact is Real men don't give a damn about lookin' Good for Anyone but a woman or a special event for Family & Good Friends!
Reason being we're men & we know with passionate hobbies "You're going to get dirty, that's what they make soap & water for, & if you aren't getting dirty then you're not doing it right!
This Country should take Pride in that as that is how it was built