No Stupid Questions

I'm going to say that somewhere between guys not wanting to wear their work clothes outside of work, and the outfits being a major symbol of workers during the time the IWW were being demonized (the IWW being the "International Workers of The World" an global socialist workers rights union) - baby clothes became a thing.

Overalls and jumpsuits and softer forms of them are easy to put on babies (due to being one garment)... Cartoons even sometimes depicted them as having a poop-flap at the back for toilet training.

So men were being told not to wear them, babies were wearing them, and they were being used as a political symbol of international communism and "lowly" blue collar work like mining or steel work.

... however women, would later (within our youth obsessed culture) want to look cute and young, and at other points in time, wanted to be seen as viable and capable workers... And women were already in the habit of borrowing fashions from men.

Thus there were cultural rejection factors for men, and cultural attraction factors for women.

A woman can put a tshirt on, some overalls and a scarf around her hair and indicate she is painting her apartment - the look thus had a social broadcasting function "I'm doing labour". If a man does this, he may well look like a garbage man, or a child in a romper suit. Male labour is now represented by more modern safety equipment, like ear and eye protection, or boots and gloves (perhaps due to harsher forms of work).

So the symbol for women of repaint and repair also transferred to television, and from there, the "look" carried popularity for social signalling, as well as started to become somewhat of a queer aesthetic for self-activated and hence partially "masculinized" women, such as lesbians, activists, hikers or environmentalists, and "independent" women, who are "doing it for themselves".