Why does Steve Bannon dress like that?

It took only a glance to see that Bannon himself cared not a whit for appearances—at least not his own.

This was, in fact, one of his defining traits.

He had spent most of his life donning the uniform of the various institutions to which he belonged: the cadet’s uniform at Benedictine High School, the all-male Roman Catholic military school he and his brothers attended in Richmond, Virginia; the naval officer’s starched whites during his eight-year stint aboard destroyers in the Pacific and the Persian Gulf; and the banker’s expensive suits, a uniform of their own, which he’d worn during his tenure at Goldman Sachs.

But once he made real money and cashed out, Bannon gleefully threw off the strictures of the working stiff and adopted a singular personal style: rumpled oxfords layered over multiple polo shirts, ratty cargo shorts, and flip-flops—a sartorial middle finger to the whole wide world.

Even now, at sixty-three, having left a right-wing media empire a few months earlier to become Trump’s chief campaign strategist, Bannon made only the tiniest concession to the Trump world’s boardroom ethos by swapping the cargo shorts for cargo pants and tossing a blazer over his many layers of shirting.

Although it was Election Night and television satellite trucks stretched for blocks around Trump Tower, Bannon hadn’t bothered with a shave or a haircut, and he had a half dozen pens clipped to his shirt placket, like some bizarre military epaulet.

“Steve needs to be introduced to soap and water,” said Roger Stone, Trump’s longtime political adviser. He looked for all the world like someone preparing to spend the night on a park bench.

from Joshua Green's 'Devil's Bargain: Steve Bannon, Donald Trump, and the Storming of the Presidency'
https://www.amazon.com/dp/B0728KHFD5