When he wasn’t penning howling critiques of the capitalist machine (or “mental Moloch”, as the poet preferred to call it), Mr Allen Ginsberg was, if this picture is anything to go by, schooling others in how to wear a piece of classic Americana: plaid. Cleverly, his own buffalo-checked shacket – though we highly doubt he’d have referred to it as such – is cut in a surprisingly modern oversized fit. If you’re thinking of investing in a similar style, our advice doesn’t deviate: size up if you want to be able to layer it over knits and the like.

If we didn’t know any better, we’d have assumed Mr Gregory Corso, the author and poet who became a key member of the Beat Generation, was auditioning for a starting role in Miami Vice. In that loose, louche white suit (not just a stylish choice, but a practical one in the Moroccan heat) and, to our eye, what appear to be slippers, we’re in no doubt that he’d have won the part. Honourable mention should go to his companion and fellow poet, Mr Peter Orlovsky, whose blazer-and-jeans pairing, though more conservative, is miles ahead of its time.

“He was simply a youth tremendously excited with life,” is how Mr Jack Kerouac characterised his creation Dean Moriarty in his rambling magnum opus On The Road. We can safely assume he would have said the same about his friend Mr Neal Cassady, who served as the model for the novel’s protagonist. Clad here – in a snap taken just a few years before the book was published – in a slightly dishevelled-looking checked blazer (perhaps the inspiration for Moriarty’s “real Western business suit”) and equally worn-in tee. He might be deep in thought, but he should have no qualms about this look.

Perhaps the most striking thing (aside from the stark presence of a single white rose) about this 1959 shot of writer Mr LeRoi Jones – who later changed his name to Mr Amiri Baraka after the assassination of Malcolm X in 1965 – is the fact that, like Ginsberg’s getup above, you can very much imagine this exact outfit being worn today. The workman’s chambray shirt and tan chinos is a classic, season-less combination and, you’ll be pleased to know, almost universally effortless to pull off.