He had that premature baldness thing going on there amongst other things.

In later life, Warhola was a paid-up member to the micro-check button-down club. All part of his look, along with black jeans, a tweed jacket from Brooks and powdered toupee.

I've always fancied a pair of clear specs, but never got around to it. Also not sure they would work so well on a bald head.

I suppose blue collar Andy was simply an appropriator of the 'Ivy League' look: as a kind of painless 'fashion' statement?

There was also some experimentation: black leather, black jeans.  This was about 1965, I should think.  Trying to intensify his profile in the slightly 'post'-Pop Art world (i.e. the move into film-making etc.). 
I approved of his reaction to the assassination of JFK, his responses to media manipulation.  A wise young bird, our Andy.

It's 'Pop Art'.  Take something banal and turn it into something that suckers want to buy and intellectuals rhapsodise over.  A can of soup.  A box of soap pads. 
Someone took him in hand, early on, and advised him about dressing well.  Then, with an increasing amount of cash to spend, it probably came naturally.  His biographers talk about his 'Oxford and chinos' look fairly early on.  Probably just obvious and inexpensive clothing for the time (circa 1960).

Today we have Grayson Perry. He does look good in a dress but I think he has given up that look.

Hockney seems to have liked a natural shoulder in his younger years but is more likely to wearing a cardi now. Wearing brightly coloured round spectacles was a good way to appear arty and interesting, less so now as the advent of cheap opticians like Specsavers has meant that anyone can get their hands on quirky eyewear easily. I've got a pair of red framed reading glasses that make me look like a mad scientist.

Fred Hughes was apparently a fan of English suits and shoes.  Handmade shirts, too.  Not a poster on DW, is he?

I finished the biography, which was worth reading, although it becomes highly depressing when Andy switches from soup tins to soft porn.
I quickly grasped his attachment to consumer culture, though.  Being from an impoverished background, unlike many of his peers, he yearned for all those American supermarket goodies: orange juice, ketchup, Coca-Cola, what-all.
Probably a nasty piece of work, though.