Gatsby at 100: Stylish Old Sport

By Matthew Longcore

Robert Redford (right) as Jay Gatsby and Sam Waterston (left) as Nick Carraway in the 1974 film adaptation of The Great Gatsby – Getty

The Great Gatsby by F. Scott Fitzgerald, widely considered to be the great American novel, was first published on April 10, 1925. To celebrate the centennial, here is a look at Gatsby’s enduring impact on style.

In an article for The Telegraph titled Why the Great Gatsby at 100 is still the most stylish man around, Jonathan Wells writes:

Gatsby’s signature style endures to this day…celebrated as a bastion of Ivy League elan. Decades of collegiate-forward fashion and preppy menswear owe a debt to the character.

The preppy look – and Gatsby’s take on style specifically – was famously fuelled by Anglophilia, says Matthew Longcore, editor of Ivy Style, creator of the Preppy Handbook Fan Club and a director at Yale University.

 

Leonardo DiCaprio as Jay Gatsby in the 2013 film adaptation of The Great Gatsby

Here is a transcript of my interview with Jonathan Wells.

JW: In Fitzgerald’s novel, there are some extraordinarily evocative passages about clothes. My mind is drawn immediately to the section around his shirts, in their “many-colored disarray”. To what extent do you think Fitzgerald captured the styles/sartorial fads of the time, and embodied/epitomised these in the character of Gatsby?

ML: Gatsby is a character whose sense of style is shaped by Anglophilia. He is “an Oxford man” who states – “I was brought up in America but educated at Oxford, because all my ancestors have been educated there for many years. It is a family tradition.”  He has a photo taken at Trinity Quad with the Earl of Doncaster. Gatsby’s Long Island mansion has a replica of “the Merton College Library.” His clothing comes from England, too – “I’ve got a man in England who buys me clothes. He sends over a selection of things at the beginning of each season, spring and fall.”

Emulating the style of English aristocracy was the fastest way for a nouveau riche American to make his new money look old. But this did not work for Gatsby’s rival Tom Buchanan, who describes these pretentions as inauthentic, suggesting that Gatsby is a parvenu from “Oxford, New Mexico, or something like that.” Of course, Daisy is much more attracted to Gatsby with his “beautiful shirts” – a dashing figure to whom she pays the ultimate compliment –  “You always look so cool.”

JW: During the intervening decades (and perhaps peaking when a screen adaptation is released) menswear enthusiasts have remained captivated by Gatsby. What do you believe, as an Ivy League style expert, gives his character and wardrobe such an enduring quality?

Ralph Lauren designed the costumes for the 1974 film adaptation.

ML: Ralph Lauren designed the 1920s menswear for the 1974 film starring Robert Redford and Brooks Brothers did the same for the 2013 film starring Leonardo DiCaprio. These films are still cherished for their sartorial splendor. The clothes in these movies are top quality, very much the timeless look of the Anglo-American gentlemen. The 1920s was the heyday of elegance in American menswear, when English-inspired brands like Brooks Brothers and J. Press set the standard for the Ivy League look.

Brooks Brothers designed the costumes for the 2013 film adaptation.

JW: Do you still believe we feel the ‘ripples’ of Gatsby and the ‘preppy’ aesthetic in modern menswear today? If so, to what extent? Is his style still specifically emulated elsewhere in in literature/culture?

ML: Gatsby is still the epitome of the classic aesthetic. When people want to get dressed up in a style embodying a bygone era, they think of Gatsby – the novel and the movies. Gatsby-themed parties have become quite popular. The Yale Club of New York City is having a Great Gatsby Party to celebrate the 100th anniversary of the novel.

JW: The pink suit, particularly, in the novel, represents Gatsby’s boldness and bravery when it comes to stylistic choices. Is he ahead of his time in this respect? Perhaps that’s why the character has stuck with us for a century; his penchant for envelope-pushing?

ML: Gatsby was definitely ahead of his time. Pink would later become the ultimate preppy color. Look at Nantucket Reds (which are actually salmon pink), Lilly Pulitzer patterns with hot pink and lime green, the classic preppy staple, the Brooks Brothers pink Oxford button-down shirt. Pink is a color that exudes confidence. Insecure men are afraid to wear pink, but confident men embrace it.

JW: Finally, as an expert in the traditions of this particular style, what are your thoughts on the screen adaptations of Gatsby throughout the years? Do you wince at any historical inaccuracies, or simply beam at the prospect of traditional fashions being bathed in the spotlight again, in any form?

ML: I truly love both films – starring Robert Redford (1974) and Leonardo DiCaprio (2013) – and I think both actors were absolutely perfect in terms of casting. The one thing I would have liked to see is a more authentic 1920s hairstyle. Both men have a side part, but in the Jazz Age, the center part was de rigueur. I hope that the next screen adaptation will have the authentic hairstyle of this era.

9 Comments on "Gatsby at 100: Stylish Old Sport"

  1. Hardbopper | April 22, 2025 at 1:27 pm |

    In the third photo from the top, captioned
    ”Ralph Lauren…”, I like the way his trousers crease sharply all the way to the instep of his shoes. They could be maybe a half inch tighter at the cuff, both front and rear, and with no break, but it is still so much better than today’s peg-leg, big-feet look.

  2. The shadows make the trousers appear to be flared, but I think they are straight cut from the knee down. They may be pleated.

  3. Unpopular opinion but here I go: jazz era costume-ish, effete, and (thusly) not a salute to the best of Ivy styling, understated and modest. The modern day incarnation of this sartorial profligacy is Pitti Uomo and similarly fashion runway-dominated styling(s). Just … ugh.

  4. I liked that book.

  5. The 2013 film costumes are much more “preppy” than the 1974 Ralph Lauren costumes, which is rather strange, considering Ralph Lauren’s obsession with the “preppy” style and his exploitation of the look over the decades. Also, neither of the films feature authentic early 1920s fashions. In both films, the fashions resemble the styles popular at the time the films were released. If I had to pick a quintessential “preppy” film, it would be Dead Poets Society.

  6. Seriously, does any anybody really think Leonardo is tough enough to run a criminal enterprise?

    I love the movie Robert Redford Gatsby movie. Great clothes, cars, music, and styled just right.

  7. Agree with S.E.

  8. Sartresky | May 1, 2025 at 12:05 pm |

    Another thumbs-up for S.E.

    By the way, the pink suit is intended to be pathetic, not admired. And Daisy cries into the shirts not because they are beautiful, but because they are gaudy and she realizes Gatsby will never fit into her world.

  9. “And so we beat on, borne back ceaselessly into the past,”

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