The Last Tycoon: Monroe Stahr’s Green Printed Shirt

Matt Bomer as Monroe Stahr on The Last Tycoon (Episode 8: "An Enemy Among Us")

Matt Bomer as Monroe Stahr on The Last Tycoon (Episode 8: “An Enemy Among Us”)


Matt Bomer as Monroe Stahr, charming studio wunderkind

Hollywood, February 1937

Series: The Last Tycoon
Episode: “An Enemy Among Us” (Episode 8)
Streaming Date: July 28, 2017
Scott Hornbacher
Developed By: Billy Ray
Costume Designer: Janie Bryant

WARNING! Spoilers ahead!


Do you celebrate Christmas in July? If so, do you struggle with finding just the right thing to wear for your holiday fun in the sun when celebrating with swimming pools and margaritas rather than snowmen and mulled wine?

On the much-too-short-lived Amazon original series The Last Tycoon, developed by Billy Ray from F. Scott Fitzgerald’s unfinished final novel, the young and dashing Hollywood hotshot Monroe Stahr (Matt Bomer) is rarely seen in anything less than a beautifully tailored three-piece suit or white tie and tails, but he gives himself a sartorial break in the name of love and leisure for a warm February morning on the terrace with his new paramour, aspiring actress Kathleen Moore (Dominique McElligott).

Ever the decent businessman and romantic partner, Monroe advises Kathleen not to sign or even discuss the details of her contract with Monroe’s studio with him without consulting her lawyer, citing that he’s well-aware that it’s his “job” to exploit her… to which she responds, “Okay, movie man. Exploit me.”

What’d He Wear?

Expert costume designer Janie Bryant brought her vast expertise and experience working on period dramas like Deadwood and Mad Men to create the enviable wardrobe for The Last Tycoon‘s elegant players from Hollywood’s fabled “Golden Age”.

The first seven episodes of The Last Tycoon established Monroe Stahr as a dapper dresser with an impressive rotation of beautifully tailored three-piece suits with elegant double-breasted jackets and interesting suitings that add much character to the debonair movie executive. We rarely see this workaholic at leisure, which makes his briefly seen casual attire all the more significant when he emerges on his terrace in the eighth episode, “An Enemy Among Us”, sporting a green Aloha shirt, cream Bermuda shorts, and loafers.

Bryant skillfully adapted a more modern approach to casual dressing with classic flair, dressing Matt Bomer in not just any off-the-rack Hawaiian shirt but one with a retro-inspired pattern and cut that could have indeed been among the summer wardrobe of the rich and famous during the latter interwar period. The modern Aloha shirt is considered to have originated in the early 1930s at the Waikiki-based King-Smith Clothiers and Dry Goods shop established by Chinese merchant Ellery Chun, who began advertising his Aloha shirts in The Honolulu Advertiser on June 28, 1935. While locals were first to take notice, buying almost all of Chen’s in-house stock, the natty shirts were quick to catch on with tourists who brought them back to the American mainland over the course of the decade.

“By the 1930s it had become synonymous with vacationing and was worn by every holidaying films tar from John Barrymore to Al Jolson, Douglas Fairbanks to Donald Colman,” John Sims wrote of the Hawaiian shirt in Icons of Men’s Style.

Monroe Stahr would have no doubt been turning heads in 1937 Los Angeles with his rich forest green camp shirt printed in vivid white and red bird silhouettes flying over the clouds with what my friend at Aloha Spotter has described as a “border pattern” of red and white palm trees bordering the sleeves, back, and the large white sew-through buttons down the plain front.


Aloha Spotter found this retro-styled shirt from Best Made that conveys the spirit, if not the exact pattern, of Monroe’s mid-’30s shirt. There are other options if you’re really leaning into the Christmas theme… but I’d recommend staying neutral.

Aloha shirts enjoyed their greatest boom in the decades following World War II, beginning with the waves of American service members who returned from serving in the Pacific with Hawaiian shirts. The dawn of the Jet Age that increased ease of travel to the Hawaiian islands in the 1950s, Hawaii’s admission to American statehood in August 1959, and the popularity of films highlighting the region like Blue Hawaii (1961) elevated the Aloha shirt to high fashion thanks to manufacturers like Alfred Shaheen and Tori Richard.

Most Aloha shirts have the classic flat camp collar with the left-side loop, but this shirt’s wide, sharp collar points are indeed more consistent with how a shirt from the late 1930s would have been styled.


Luckily for Monroe, his warm day at home is made more palatable by the era’s increasing acceptance of shorts for men. Like much of popular menswear, shorts have a military pedigree that, in this case, extends to the days of the British empire when the British Army was seeking more comfortable alternatives to uniform trousers in tropical and desert climates. By the roaring ’20s, bankers and businessmen in Bermuda were inspired by the new military garment and soon adopted shorts of their own, establishing what would become an accepted business uniform in Bermuda of wearing a jacket, tie, and heavy gray wool knee socks with a pair of tailored flannel shorts that extended to approximately six inches above the knee.

As tourism to Bermuda increased over the following decade thanks to the expansion of air services to the islands, travelers took note of the trend and began spreading the practice of wearing shorts back to the United States, Canada, and England. The popularity of “Bermuda shorts” and their newfound association with tropical leisure rather than business meant seeing shorts in brighter and lighter fabrics rather than the staid gray flannel of the Bermuda business uniform. By the late 1930s, Bermuda shorts had a firm stronghold among the leisurewear of America’s upper class with no less than General George C. Marshall enjoying the world’s last peacetime summer before World War II, sporting a summer-weight sport jacket, bow tie, and Bermuda shorts in this August 1939 photo from Fire Island. (You can read more about the history of Bermuda shorts in these articles from Brand Riddle, Condé Nast Traveler, and GARMANY.)

Monroe plays it safe by restricting his Bermuda shorts to his home, sporting a pair of cream pleated shorts that rise a few inches above his knees. The shorts have side pockets and jetted back pockets with the back left pocket closing through a loop.

To co-opt another F. Scott Fitzgerald's titles (itself borrowed from Rupert Brooke), one could say that Monroe Stahr has landed in this side of paradise.

To co-opt another F. Scott Fitzgerald’s titles (itself borrowed from Rupert Brooke), one could say that Monroe Stahr has landed in This Side of Paradise.

Monroe appears to be wearing brown leather penny loafers, another indication of his cutting-edge style as this type of shoe had only been developed the previous year by G.H. Bass & Co.

Since the shoe’s inception in 1936, the Wilton, Maine-based manufacturer has marketed the shoe as “Weejuns” (from “Norwegians”), though the American prep school practice of sliding a penny into the distinctive diamond-shaped slit in the leather strip across the shoe’s saddle popularized its “penny loafer” moniker.

Again, with apologies to F. Scott's titles, this screenshot could easily be captioned The Beautiful and Damned.

Again, with apologies to F. Scott’s titles, this screenshot could easily be captioned The Beautiful and Damned.

Monroe wears his gold signet ring with an etched “S.” on his right pinky. Though the letter no doubt signifies his adopted professional surname of Stahr, it could also stand for his birth surname of Sternberg.

How to Get the Look

Matt Bomer and Dominique McElligott on The Last Tycoon (Episode 8: "An Enemy Among Us")

Matt Bomer and Dominique McElligott on The Last Tycoon (Episode 8: “An Enemy Among Us”)

Not surprising for an L.A. wunderkind, Monroe Stahr proves to be on the forefront of the fashion battleground, adopting modern menswear staples that had only just been introduced like the Aloha shirt (1935), Bermuda shorts (1920s), and penny loafers (1936). This casual and comfortable ensemble also sets an unintentional template for a classic approach to channeling some holiday color for a summertime adventure.

  • Forest green Aloha shirt printed in white-and-red palm tree “border pattern” and white-and-red flying birds-over-clouds pattern with wide sharp camp collar, plain front, and short sleeves
  • Cream pleated Bermuda shorts with side pockets and jetted back pockets (with back left button-loop closure)
  • Brown leather penny loafers
  • Gold monogrammed signet ring, right pinky

Several retro-minded retailers carry a selection of Bermuda shorts that would suit the purpose here such as Mango, with its Bermuda shorts in sand-colored cotton or off-white linen, and Scott Fraser Collection, with the brand’s vintage-inspired high-waisted riviera shorts complete with pleats and button-tab side adjusters.

Do Yourself a Favor and…

Check it out on Amazon Video. It’s truly a shame that The Last Tycoon had to end its run after just a single nine-episode season as it was a well-acted, well-dressed, and well-plotted series that showed plenty of promise for future storytelling.

Of course, you could also read F. Scott Fitzgerald’s novel The Love of the Last Tycoon and watch the first cinematic adaptation, released in 1976 starring Robert De Niro as the debonair but doomed Monroe Stahr.

The Quote

It’s my job to exploit you!


I had always believed “Christmas in July” to be a more modern concept until I recently learned of a 1940 film directed by Preston Sturges entitled Christmas in July starring Dick Powell, Ellen Drew, and Sturges stock player William Demarest. Curiously enough, production on Christmas in July lasted from June 1 to June 29, 1940, ending just two days before the actual month of July!

One comment

  1. George

    Brad Pitt wears a cool Aloha shirt in the new Tarantino film “Once Upon A Time In Hollywood”. Should give you a lot to post about, great clothes and cars – amazing, amazing movie

Leave a Reply