From Jay Gatsby to American Psycho’s Patrick Bateman, here are the sharpest characters in the Western canon.

According to an estimate cooked up by the algorithm masterminds at Google HQ in 2010, 129,864,880 books had been published since the beginning of literary history. That’s clearly more than even the most committed bibliophile could devour in a lifetime. With so many scholarly works kicking about, it makes sense to earmark those that are going to be of the greatest use to you. If you’re reading this, chances are you have more than a passing interest in sartorial matters, so we thought we’d help you with that shortlist, with five novels featuring some of the most stylish men in literature. You’re welcome.

by Mr F Scott Fitzgerald

Anyone who has read Mr F Scott Fitzgerald’s masterpiece will recall the scene when Jay Gatsby decants the contents of his plush wardrobe in front of an admiring audience: “He took out a pile of shirts and began throwing them, one by one, before us, shirts of sheer linen and thick silk and fine flannel, which lost their folds as they fell and covered the table in many colored disarray… he brought more and the soft rich heap mounted higher – shirts with stripes and scrolls and plaids in coral and apple-green and lavender and faint orange, with monograms of Indian blue.” This devotion to fine attire wasn’t just limited to shirts – which incidentally, were made by Turnbull & Asser in the 1974 film adaptation starring Mr Robert Redford – it also extended to suiting, and he dons a particularly fetching pink two-piece in the novel, much to his rival Tom’s Buchanan’s disdain. Clearly, Mr Gatsby was ahead of his time, as pastel shades are most certainly in.

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by Mr Bret Easton Ellis

Mr Bret Easton Ellis’ American Psycho epitomises the amoral consumerism of 1980s yuppie culture, but it’s also a luxury label junkie’s dream. Peppered liberally throughout the novel are passages that intricately detail the outfits of the anti-hero protagonist and narrator Patrick Bateman, who wins hands down for the most sartorially fluent killer ever imagined. “The doors shut. I am wearing a mini-houndstooth-check wool suit with pleated trousers by Hugo Boss, a silk tie, also by Hugo Boss, a cotton broadcloth shirt by Joseph Abboud and shoes from Brooks Brothers… I step out of the elevator, brushing past a hung-over Wittenborn, swinging my new black leather attaché case from Bottega Veneta.” Other notable sartorial gems include a wool and silk Ermenegildo Zegna suit, countless Ralph Lauren pieces and a Valentino Couture tie. By the end of the novel, you’ll be left with the impression the man is a walking billboard for the Paris and Milan houses, and quite likely, a feeling of slight nausea on account of his numerous depraved homicidal acts.

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by Mr Jack Kerouac

Mr Jack Kerouac’s seminal work On The Road came to be the defining novel of the 1950s Beat Generation. Essentially a roman à clef of Mr Kerouac’s own life and travels with leading Beat writers of the age, he famously boasted that he wrote the entire first draft in three weeks without stopping, by typing on a continuous sheet of paper and surviving off of a heady mix of Benzedrine, coffee and quite probably, a margarita or five. It’s Dean Moriaty – the character inspired by real-life comrade and Beat Mr Neal Cassady – that proves being well-put-together isn’t all about starched collars and tailoring: “His dirty work clothes clung to him so gracefully, as though you couldn’t buy a better fit from a custom tailor but only earn it from the Natural Tailor of Natural Joy, as Dean had, in his stresses”. It’s his blithe mix of plaid shirts, utilitarian workwear and love-worn denim that earns Moriaty a place in the literary style hall of fame. Fellow Beat author Mr William S Burroughs later said that the novel “sold a trillion Levi’s, a million espresso coffee machines”.

by Mr Evelyn Waugh

Mr Evelyn Waugh, who experienced the hedonistic lifestyle of the 1920s Bright Young Things firsthand, had a knack for creating characters that personify the very British tradition of the dapper eccentric. His 1945 novel Brideshead Revisited – widely considered to be his greatest work – sees Charles Ryder tell the story of his doomed friendship with the troubled son of a Catholic Marquis, Lord Sebastian Flyte, who is always impeccably dressed – at the start of the novel, at least. “Sebastian entered – dove-grey flannel, white crêpe de chine, a Charvet tie, my tie as it happened, a pattern of postage stamps”. Set against a backdrop of a grand English country house, the spires of Oxford and the canals of Venice, the novel is a must-read for anyone who has an appreciation for classic British attire and the vagaries of the English upper class.

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by Ms Patricia Highsmith

Dickie Greenleaf, who lives a life of indulgent, bohemian luxury on the Neapolitan coast, has self-confidence in spades – the sort that’s often inherent to the sartorially inclined. Here’s how Ms Patricia Highsmith described him: “Dickie was handsome. He looked unusual with his long, finely cut face, his quick, intelligent eyes, the proud way he carried himself regardless of what he was wearing. He was wearing broken-down sandals and rather soiled white pants right now, but he sat there as if he owned the Galleria”. The fact the book is set on the Italian Riviera in the 1950s only furthers its style credentials. And it has to be said that Mr Jude Law’s Ivy League-meets-suave-beach-dweller in the 1999 film more than delivers the louche swagger suggested by the novel.

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