Dollars, Deals, and Dicaprio: The Rise and Reinvention of the Finance Bro on Screen
Lifestyle
By: Eton • 8 minOnce upon a time, the finance bro was king—swaggering into corner offices in power suits, wielding overconfidence like the tickertape funning across the Morgan Stanely in Times Square Building during a bull market and dropping terms like “arbitrage” into conversations at banal cocktail parties. Hollywood took notice, creating characters who were equal parts aspiration and cautionary tale—charismatic, reckless, and occasionally imprisoned. From the sharp-elbowed excess of Wall Street to the meme-fueled market maneuvers of Dumb Money, the finance bro has evolved, reflecting every major financial shift over the past 75 years.
From Bro to Pro
Now, as new finance bros replace trading floor gladiators, the uniform has changed—dress shirts, tech vests, and caps have taken over, while ties are no longer a requirement but a style choice. One question remains: has the finance bro leveled up—or just rebranded?
The Foundations of The Finance Bro: The 1950s-1970s
The finance bro archetype didn’t emerge overnight—he was built in the boardrooms of mid-century corporate America, where power was defined by hierarchy, backroom deals, and a firm handshake (and if you weren’t part of the old boys’ club, good luck getting a seat at the table). While the excess of later decades had yet to take hold, these films and shows laid the groundwork for financial ambition, highlighting power struggles, satire, and the allure of wealth in a post-war world. The finance world was evolving, but let’s be honest—it was still a men’s club where ambition wore a three-piece suit, and women were often relegated to the margins.
In the 1950s, finance was still an exclusive, suit-and-tie affair. Double-breasted suits, short-brim fedoras, crisp white shirts, pocket squares, and conservative silk ties signaled authority. Bow ties remained popular, and pinstripes emerged as a signature look. Power was projected through tailoring, not flash. By the 1960s, the look softened slightly, with slimmer lapels and lighter fabrics, but structure and formality remained essential. In the 1970s, a touch of leisure began to creep in—mustaches, slightly longer hair, and a looser approach to suiting. Still, the finance bro remained buttoned up during work hours.
Executive Suite (1954)
A tense corporate drama set in the wake of a CEO’s sudden death, this film explores the power dynamics, ambition, and ethical dilemmas of high-stakes business. The executives, clad in impeccably tailored gray robust wool suits and crisp white shirts, embody mid-century corporate authority before Wall Street’s wild excess took hold.
The Solid Gold Cadillac (1956)
This satirical comedy skewers big business and corporate greed, following a small-time shareholder who takes on a corrupt board of directors. Here, finance bros wield double-breasted suits and bow ties like armor, reinforcing the rigid formality of post-war America’s financial elite.
The Wheeler Dealers (1963)
Set in the early 1960s, A sharp-witted comedy about a Texas oil tycoon navigating Wall Street, this film introduces a larger-than-life finance character who thrives on charm and deal-making. He brings a different kind of swagger to Wall Street, pairing tailored suits with a hint of Southern flair—think bolder patterns, flashy cufflinks, and a cowboy hat always within reach.
The Birth of the Finance Bro: The Greed Decades (1980s–1990s)
The 1980s and 1990s saw the finance bro fully formed—his power suit sharper, his ambition bolder, and his disregard for consequences greater. This was the era of excess, where Wall Street’s golden boys made fortunes overnight and lost them just as quickly. The finance bro became a symbol of both success and reckless greed, as Hollywood captured his rise, fall, and insatiable hunger for more. From ruthless corporate raiders to high-flying hedge fund hopefuls, these films and shows cemented the finance bro as a cultural force—one that was both admired and despised.
Finance bros were walking billboards of their own success—tailored power suits, contrast-collar shirts, suspenders, and statement-making Rolex watches. It was an era of boldness: wider lapels, structured shoulders, and aggressive sartorial choices that signified wealth and power. Suits weren’t just clothes—they were armor, designed to dominate the trading floor or boardroom. Accessories became status symbols: Montblanc pens, oversized mobile phones, and Patek Philippe watches that screamed, I made it. Even business casual had an edge—think boxy blazers and pleated trousers paired with driving loafers, effortlessly signaling affluence. As the 90’s approached the boxy silhouettes softened slightly, but power still ruled. Double-breasted suits, bold-patterned ties, and thick-framed glasses became the uniform for hedge fund titans and ambitious young traders. The accessories shifted, too—cell phones shrank, watches remained oversized, and business casual meant loose pleated dress pants with an ill-fitted blazer—bonus points for the Gordon Gekko slick back still holding strong.
Wall Street (1987)
The definitive finance bro film Set in the mid-1980s, Wall Street follows Bud Fox as he falls under the spell of corporate shark Gordon Gekko, who preaches the gospel of greed. Gekko’s sharp-shouldered power suits, contrast-collar shirts, and signature suspenders became the uniform of ambition. The more ruthless the deal, the better the tailoring.
Family Ties (1982–1989)
In this sitcom Set in the 1980s, Alex P. Keaton, played by Michael J. Fox, is the ultimate young finance bro in the making. A Reagan-era Republican in a family of former hippies, Alex is obsessed with capitalism, stocks, and making it big, embodying the yuppie ethos of the decade.
The Fall and Reinvention: 2000s–2010s
The 2000s and 2010s marked a reckoning for the finance bro. The high-flying excess of the previous decades came crashing down with the 2008 financial crisis, exposing the dark underbelly of unchecked ambition. Wall Street’s golden boys were no longer just symbols of wealth—they became villains in the public eye. This era’s films and shows shifted from glamorizing finance to critiquing it, peeling back the layers of corruption, greed, and moral decay. The finance bro was still around, but he was now being forced to answer for his actions.
The post-dot-com era finance bro still embraced the power suit, but the tailoring slimmed down slightly from the boxy silhouettes of the ‘90s. Business casual began creeping in—light blue dress shirts, pleated chinos, and leather loafers without socks became acceptable in the office. Accessories became more minimalist; Panerai and Breitling watches replaced the chunky Rolex, and the BlackBerry became the finance bro’s lifeline before the iPhone took over. By the 2010s The finance bro began a full sartorial transition—Patagonia vests over dress shirts became the new uniform, signaling a move toward a more relaxed, tech-influenced aesthetic. Ties became optional, replaced with open-collar shirts, slim-cut suits, and Allbirds sneakers on casual Fridays. The hedge fund world perfected the finance casual look, where a bespoke suit and an ultra-lightweight down vest could coexist in the same outfit—because nothing says power like dressing like you could retire tomorrow but choose not to.
American Psycho (2000)
Set in the late 1980s, this dark satire follows Patrick Bateman, a high-powered investment banker obsessed with the perfect business card and designer suits as much as he is with murder. His impeccable monogrammed Valentino suits, pristine Hermes silk ties, and custom Loro Piana loafers reflect his desperate need for dominance in a world where wealth is an illusion measured by aesthetics, wealth is a carefully curated illusion, and the right suit can be just as sharp as a knife.
Boiler Room (2000)
Taking place in the late 1990s, this film dives into the world of shady brokerage firms, where young finance bros are trained to sell worthless stocks with ruthless efficiency. It’s a cautionary tale of unchecked ambition, quick money, and the consequences of playing the game without knowing the rules.
Margin Call (2011)
Set in 2011, this razor-sharp drama takes place over a tense 24-hour period at an investment bank on the brink of collapse. The finance bros in Margin Call have traded the flashy suits for sleeker, muted power dressing—dark navy and charcoal suits, understated ties, and a more somber, crisis-mode aesthetic. The film explores the moral compromises made in the name of profit, capturing the moment finance bros realized the house of cards was falling.
The Wolf of Wall Street (2013)
Spanning the late 1980s into the 1990s, Martin Scorsese’s frenetic masterpiece chronicles the rise and fall of Jordan Belfort, a stockbroker who turns finance into a circus of fraud, excess, and debauchery. Double-breasted suits, garish ties, and designer sunglasses complete his transformation from finance upstart to Wall Street kingpin.
The Big Short (2015)
Set in the mid-2000s, this darkly comedic exposé of the 2008 housing market crash follows a handful of finance outsiders who saw the collapse coming and bet against the system. Finance bros in this film are less about polish and more about strategy—ill-fitting blazers over hoodies, unbuttoned shirts, and casual loafers signal a shift toward a more irreverent, Silicon Valley-inspired take on finance. The film brilliantly dissects the greed-driven implosion of Wall Street with wit and clarity.
The Apprentice (2004–2017)
Taking place in the 2000s and 2010s, Reality TV’s most infamous business competition show, The Apprentice turned corporate ambition into entertainment. With its dated power dressing aesthetic—boxy suits, ill fitted bold ties, and over-the-top bravado, it blurred the lines between finance, power, and spectacle, making finance bros not just money-makers but media personalities. Something holding on to an aesthetic fromo yesteryear, but recently it seems that Mr. Presedent has finally consulted a stylist with a sliver of taste who had him fitted for a suit from this era, finally.
Billions (2016–2023)
Set in the 2010s, This award-winning, high-stakes drama dives deep into the ruthless world of hedge funds, following the cat-and-mouse battle between a billionaire finance bro and the U.S. Attorney determined to take him down. Billions captures the modern evolution of the finance bro—smarter, slicker, and more legally dubious than ever, donning perfectly tailored suits, luxury watches, and tech-infused finance casual, where a Patagonia vest and a custom-tailored suit can coexist.
Crypto, Casual, and Quiet Luxury: Reinventing the Finance Bro (2020s)
The modern finance bro has swapped his power suit for an ultra-light puffer vest, his trading floor for a Twitter feed, and insider tips for Reddit-fueled market revolts. This is the era of the digital disruptor—finance bros who've pivoted from hedge funds to startups, meme stocks instead of blue chips, and investing as social-media spectacle. Post-2008, the finance bro cleaned up his act: tech vests, tailored joggers, and limited-edition sneakers replaced the excesses of past decades. Crypto millionaires and fintech disruptors adopted a hyper-casual-meets-luxury aesthetic, trading from Discord rather than the trading floor, flexing NFT screenshots instead of Rolex watches. Now, however, a pivot back to subtle sophistication is underway, as finance bros embrace sleek tailoring, thoughtful layering, and understated luxury—a balancing act between calculated cool and quiet refinement.
Succession (2018–2023)
Covering the late 2010s to early 2020s, Succession is the ultimate generational finance bro drama. It isn’t just about business—it’s about legacy, privilege, and how the finance bro’s worst enemy is often himself (or his equally power-hungry family). The Roys may have wealth, but do they have any self-awareness? Probably not. Their aesthetic? Bespoke tailoring meets quiet luxury—stealth wealth dressing with cashmere polos from Monticelli, minimalist Loro Piana loafers, and a “no labels” approach to excess. The vest seen on each character, but with a price tag a notch up fro the regular finance bro.
Super Pumped (2022)
Set in the late 2010s, this gripping dramatization of Uber’s rise showcases the tech finance bro: a disruptor who plays by his own rules, fueled by ambition, arrogance, and an utter disregard for tradition. The wardrobe? T-shirts under blazers, sneakers in the boardroom, and a casual disregard for classic finance bro power dressing. It’s a cautionary tale of innovation turned toxic.
Industry (HBO, 2020–)
Set in present-day London, this dark, unfiltered look at high finance through the eyes of ambitious young bankers captures the high-pressure hustle culture of modern finance. Here, the new finance bro aesthetic takes shape—tailored suits mixed with relaxed, Gen Z-inspired officewear, showing how today’s finance elite balance authority with a looser, globalized dress code.
From Bro to Pro: The Evolution of the Finance Bro
The finance bro is at a crossroads. No longer just a reckless trader in an Armani suit, today’s finance bro is starting to realize that screaming “Buy the dip!” on Twitter isn’t a long-term investment strategy. ESG funds, responsible investing, and financial literacy are starting to creep into the finance bro’s vocabulary, though whether it’s for the planet or just for optics is still up for debate. The modern finance bro has more tools at his disposal than ever before—YouTube traders, TikTok financial gurus, and the ability to go viral with a single market take. But will he actually use this knowledge for good, or is he just swapping Wolf of Wall Street excess for Silicon Valley spin?
Hollywood has spent decades both glorifying and skewering the finance bro, portraying him as everything from a ruthless dealmaker to a cautionary tale of unchecked ambition. His image has evolved from Wall Street kingpin to hoodie-clad startup bro, but at his core, he remains the same: ambitious, self-assured, and always looking for the next big opportunity.
So, where does he go from here? Is this the dawn of the finance pro—thoughtful, strategic, and maybe even ethical? Or will history repeat itself, with another generation of finance bros crashing the economy, one risky bet at a time?
Either way, one thing is certain: if he’s wearing Eton, at least he’ll look good doing it.
Image Credits & Fair Use Disclaimer:
The images used in this article are sourced from [MovieStillsDB.com & cinemateral.com] and are credited to their respective copyright holders. They are used here for editorial and educational purposes to illustrate the evolution of finance culture in film and television. No copyright infringement is intended. If you are the rights holder and wish for an image to be removed, please contact us at [email protected].
