From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Whether you’re looking for light colours, simple stripes or the most roaring accessories for summer, here’s how to take inspiration from The Great Gatsby…

This weekend, we mark the 96th anniversary of F. Scott Fitzgerald’s seminal novel, The Great Gatsby. Chocked full of mysterious millionaires, flappers, speakeasies and jazz, it’s a Champagne-soaked tale that is still influencing audiences today — and has been adapted for screen multiple times. The first film version was a black-and-white silent affair in 1926; the most recent, 2013’s Leonardo DiCaprio-starring take.

And, while the book details many styles and fashions of the time — from Gatsby’s ‘beautiful shirts’ and radical new ‘sweatshirts’ to the cream suits and pinstripes worn by the upper classes — the silver screen adaptations have most notably inspired the wardrobes of modern men. So, as the great American novel approaches its centenary, let’s see what style lessons we can learn from the original old sport, Jay Gatsby.

Don’t be afraid of wearing pink

You heard us. Even in Fitzgerald’s novel, the author writes at length about Gatsby’s penchant for pink. Tom Buchanan exclaims “An Oxford man! Like hell he is! He wears a pink suit!” when badmouthing Gatsby — and Daisy Buchanan later can “think of nothing except the luminosity of his pink suit under the moon”. It’s a divisive colour, as the Buchanans’ reactions prove. But pink is nothing the modern man should be afraid of.

In fact, you should embrace the colour. Just look how good Redford and DiCaprio look in the shade. So, if you do decide to go full Gatsby, Tom Ford’s ‘Shelton’ suit is suitably salmon. Otherwise, incorporate the colour in subtler ways — such as an Emma Willis shirt or a pair of softly-striped Hemingsworth swim shorts, perfect for a dip in the pool (just clear the area of disgruntled garage owners before you dive into the deep end…)

From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Tom Ford Shelton Twill Suit

£3300

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From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Emma Willis Superior Cotton Shirt

£200

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From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Hemingsworth Seersucker Swim Shorts

£185

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Embrace the colour combinations of Gatsby’s summer suiting

“An hour later,” reads a passage from Fitzgerald’s novel, “the front door opened nervously, and Gatsby in a white flannel suit, silver shirt and gold-colored tie hurried in”. It doesn’t paint the protagonist in his most charming, charismatic light, but this look has been replicated in almost every on-screen adaptation (even the disastrous made-for-TV attempt in 2000). And for good reason — it’s a masterclass in light, bright summer suiting. 

So, if you’re heading to a wedding this summer, take note. Start with a pale grey shirt, such as Turnbull & Asser’s  unreasonably breathable cashmere-cotton blend button-up. Add a subtly gold tie — something like this tight ‘Daisy’ design from Emma Willis. And top things off with the brightest, whitest suit or blazer you can find. We’d avoid Gatbsy’s thick-handled flannel fabric, though, and instead opt for lightweight linen from Drake’s. 

From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Drake’s Ecru Games Blazer

£795

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From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Turnbull & Asser Grey Shirt

£325

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From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Emma Willis Gold Silk Tie

£120

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Remember, sweaters are just as important as suits

But it’s not all gold neckties and pocket squares. Sometimes, even thriftless millionaires have to dress down. And Gatsby does — albeit more so on film than in the novel. In Fitzgerald’s source material, Jay Gatsby tends only to wear sweatshirts during his previous life as James Gatz, spending hours “loafing along the beach in a torn green jersey and a pair of canvas pants”. In the films, his knitwear is a little more glamorous.

DiCaprio, especially, embraced luxurious jerseys and jumpers. His caramel-coloured knitwear was exquisitely woven and impossibly fine. To follow his natty lead, look no further than Artknit Studios’ mulberry silk sweater, or this cable-knit option from kings of prep, Ralph Lauren. Alternatively, give a West Egg-appropriate nod to the nautical with Hemingsworth’s striped raglan sweatshirt. 

From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Artknit Studios Silk Cotton Sweater

£137

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From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Hemingsworth Pablo Raglan Sweatshirt

£115

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From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Ralph Lauren Cable-Knit Jumper

£395

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Invest in your shirts — but don’t throw them around

“He took out a pile of shirts and began throwing them one by one before us,” reads one of the most famous passages of Fitzgerald’s novel. “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. While we admired 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.”

It’s a dizzying image. And, although we wouldn’t recommend treating your own shirts with such disdain, it certainly pays to invest in these essentials. In the 1974 Robert Redford adaptation of The Great Gatsby, the titular millionaire’s shirts were provided by Turnbull & Asser, the heritage Jermyn Street shirtmaker. And there’s no better place from which to source yours.

From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Turnbull & Asser ‘The Great Gatsby’ Shirt

£225

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From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Turnbull & Asser Pink Cashmere Shirt

£325

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From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Turnbull & Asser Lilac End-On-End Shirt

£250

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No outfit is complete without a signature hat

There’s not much written about Gatsby’s hat collection. He’s often depicted swanning around his estate “with hat and light overcoat in hand” — but never in much detail. Instead, the film adaptations gave the character’s fedoras and flat caps time to shine. And, from Leonardo DiCaprio’s straw boater (a style, sadly, that is yet to re-emerge into the fashion mainstream) to Robert Redford’s Panama hat, there is lots to like.

Perhaps the most striking style is the wide-brimmed straw hat; wrapped in a thick, dark ribbon and paired with a dark suit. It’s a strong look, and one you can replicate this summer if you buy from Lock & Co, or the lesser-known Borsalino. Alternatively, for those Sunday roadtrips, take soft-peaked inspiration from Redford’s Gatsby, and pull on a Brunello Cucinelli linen flat cap. 

From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Brunello Cucinelli Linen Flat Cap

£270

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From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Borsalino Crochet Raffia Hat

£210

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There’s no pattern more timeless than a simple stripe

Next up, a timeless pattern with a special place in screen Gatsby’s heart; stripes. Be they pin-thin or broad and bold, actors from 1949’s Alan Ladd to 2000’s Toby Stephens have buttoned up, pulled on or tied together clothes bearing this simple, sophisticated motif. But no on-screen iteration loved a stripe more than Robert Redford — whose shirts, suits and even swimwear were striped.

We love the look. Especially DiCaprio’s stripe-on-stripe braces; perfect for a summer garden party or wedding. Huntsman’s plaited design is particularly ‘roaring’. Then there are his shirts. Blue and white is a classic pairing, epitomised here by New & Lingwood. And, of course, the classic pinstripe suit. It’s slimming, sophisticated, and tailored to a tee here by Hackett. 

From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Huntsman Airforce & White Braces

£110

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From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Hackett Savile Row Stripe Wool Suit

£660

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From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

New & Lingwood Blue Stripe Shirt

£145

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Black tie, as the name suggests, should be all about your neckwear

And finally, we turn to the tuxedos. It had to happen eventually. Because, even though Fitzgerald didn’t often have his characters don dinner jackets, The Great Gatsby film adaptations are renowned for their bespoke, buttoned-up approach to the dress code. And the highlight of these decadent ensembles? Those black ties themselves.

In the Robert Redford version, the actor even wears white tie. But, as that’s a sadly dying dress code, let’s focus on the black. The lesson here, as with Gatsby’s style as a whole, is to stand out. Whether you go big and bold like Redford, and choose this large Tom Ford option, or add some interest like DiCaprio by opting for either Oliver Brown’s velvet tie or Favourbrook’s patterned design, your bow tie should always take centre, Champagne-toasting stage.

From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Oliver Brown Velvet Bow Tie

£65

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From Redford to DiCaprio, here are the greatest style lessons to learn from Jay Gatsby

Favourbrook Black Berries Bow Tie

£85

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Want more movie star style inspiration? How to wear all white and look like Steve McQueen…

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Further Reading