(Bloomberg) -- One of the more pivotal scenes in The Apprentice takes place in a tailoring shop. The film, which hits theaters on Friday, Oct. 11, is essentially a Donald Trump origin story. It charts the mentorship and dubious legal support that the then-future-president (played by Sebastian Stan) received from the controversial and charismatic lawyer Roy Cohn (Succession’s Jeremy Strong) early in his real estate career.
The movie begins in the late 1970s, when a young Trump is working for his father, Fred, collecting overdue rent from public housing projects. He learns about business and life from the older man as he begins building his Manhattan real estate empire, marries the flashy model Ivana and elbows his way into New York’s cutthroat social scene.
It takes place in a New York that’s coming out of a downtrodden period, turning into one drunk on power, money and excess. The movie ends in 1983 as Trump starts working on his book The Art of the Deal, which would cement his reputation (apocryphal as it may be) as a shrewd self-made billionaire.
In that wood-paneled shop, Cohn, then an outsize pugnacious and amoral presence in the halls of New York’s court system, shows his young protege how to dress if he wants to fit in with New York’s polite society.
The scene takes place early in the film as Cohn helps land Trump a tax break on a building. He then starts tutoring the ambitious and power-hungry Trump, parsing out advice and teaching him one of his most closely-held lessons: that style can often overshadow substance.
“Looks expensive,” Cohn says when the tailor slips on the suit. “We’ll take it.” When Trump says he can’t afford the suit, Cohn gives him back his lawyer’s fee, cementing their allegiance. “If you look like a million bucks, then I look like a million bucks.”
Then they look at Trump, now in his well-fitting navy suit, and he says, “Does this look like a guy from Flushing or a guy from Fifth Avenue?”
Laura Montgomery, the movie’s costume designer, says that era had many unspoken rules for how men should dress. “There wasn’t a lot of latitude in terms of style,” says the designer, who has worked on Suicide Squad and won an Emmy for her work on What We Do in the Shadows. “It was J. Crew to Brooks Brothers to Canali to Brioni. You just climb that ladder, and everyone conforms to that.”
Brioni is mentioned by name in that scene, and it remains a Trump favorite. The Kering-owned, Roman tailoring line is known not only for its high-quality cuts, but also for being the first brand to stage a men’s fashion show, and, for a time, its bold use of colors. Founded in 1945, it remains one of the more revered—and classic—men’s labels, and its made-to-measure suits in particular are heralded as the ne plus ultra in men’s suiting.
The suit in the film was not, however, a Brioni. “It was actually a custom suit that we made,” Montgomery says. “But it represents this leveling up. It’s a brand that people wear when they’ve achieved a certain amount of success, and it signals that.”
For Montgomery, period authenticity was a chief concern—especially considering she was conjuring the world of wealth and social rank in Manhattan, and its obsession with appearances, all while working on an independent film’s budget. She also wanted to avoid any stereotypes of the era, which meant no power banker tropes: no stripes, contrast collars, football-worthy shoulder pads or swaggering folds of Armani that were represented in films such as Wall Street (1987) and American Psycho (made in 2000 but set in 1987).
All of that started to take hold after 1983. “I tried to make it look more naturalistic, because these are real people,” Montgomery says. “I didn't want it to feel too comedic.” So she looked to day-to-day images, such as family photos, to get a more accurate idea of what men wore, to inspire the 20 suits for Trump and 10 or so for Cohn, some of which were made and others sourced or rented. In the end, she says, “it’s a lot about the collars and the structure of the suits.”
The clothes, however, do subtly communicate the changing fortunes of each of the two main characters. “They have their own character arc,” Montgomery says. “For Donald, when the movie starts in the 1970s, he doesn’t have a good sense of style. People comment on his cheap suits.” In the earlier scenes, Trump’s suits often look sort of forlorn and come in odd colors. “But as he gets more money and is tutored by Roy, his style becomes more elevated.”
Cohn, on the other hand, has a downward trajectory. When we meet him, he’s at the apex of his professional and social life, wearing ostentatious tailored outfits, mostly in lighter shades. “He’s never in black. He’s always in a very light, neutral palette—beige, light blue, an amazing pistachio green. I remember Jeremy brought in this photo of a Dries [Van Noten] robe that was this amazing, like, silver-sage, and we found a fabric like it and made a tuxedo for him out of it.”
Cohn was a colorful figure, a conservative power broker whose sexuality was something of an open secret. So he also indulges in theatrical moments, such as when he conducts meetings from his home in eccentric (and slightly feminine) patterned robes or dons fur coats.
“He was, to me, the most interesting character, because of all of the contradictions,” Montgomery says. “He was somebody who was in some ways very closeted, who denied being gay, who denied having HIV and AIDS, but also lived a very flamboyant lifestyle and didn’t seem to hide that from his close circle. There are photos of him conducting business meetings in these silk robes that just screamed sex.”
And yet, toward the end of the movie, he is a diminished figure, in terms of both his physicality and his status. So Montgomery had to create the sense of him shrinking with more oversize clothing. (It should also be noted that Strong has an almost distracting tan, which was another Cohn signature.)
But perhaps the most telling moment comes at the end, when Trump, whose presence in the worlds of real estate and media is beginning its breakneck ascent. In the scene, he’s looking out from his Midtown office onto the city’s skyscrapers. After he rifles through many patterned and colored ties, Montgomery deploys an iconic color as a visual foreshadowing.
“The red tie,” she says. “We saved that one for the very end.”
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