Wealth and power are two of the most common traits we associate with famous investors. Naturally, this image also entails a certain profile in style. We are all familiar with the saying “dress for success.” In the investing world, dressing for success can take on a whole new meaning.
However, a close examination of wealthy investors reveals that not all are sporting peak lapels, designer shoes or luminous Rolex watches. Some are perfectly content wearing blue jeans and a t-shirt. Others, like 2016 presidential Candidate Donald Trump, get noticed for other stylistic elements that have more to do with what they wear on their head rather than which suits or clothes they pick out. For this reason, we thought it would be interesting to profile five well known investors and business tycoons across the style spectrum.
When looking at Mark Cuban, it’s difficult to see a man who has any professional endeavours, let alone is worth $3 billion. The owner of the Dallas Mavericks made his billions in the dot-com era of the 1990s, where he developed and sold an online video portal to Yahoo for $5.7 billion. Since then, he can be seen courtside at Mavericks games wearing silly t-shirts and faded jeans. It’s unknown whether he ever gets the chance to comb his hair.
The renegade billionaire known for skydiving and trying to navigate the Atlantic in a powerboat doesn’t think much of ties or expensive suits in general. It therefore comes as no surprise that Branson doesn’t enforce a dress code at Virgin, his flagship company.
“Personally, I think all employers should drop the dress code and let their teams wear whatever they feel most comfortable in,” Branson says.
While certainly no slouch, Branson is usually seen in public wearing a plain, buttoned up dress shirt and jeans. The sports jacket is optional.
Larry Ellison is what you’d expect to see when looking at a billionaire. The tech investor and founder of Oracle has been described as a power dresser, sporting double-breasted suits, peak lapels and beautifully tailored clothes that not only compliment his features, but give him an exceedingly dominant, confident look. Since fading into the background at Oracle, Ellison has eased off a bit on the neckties and sharp ensembles, but continues to lead in style. After all, what would you expect from a man who purchased a Hawaiian island for $600 million? Ellison’s immaculate dress code is consistent with his other expensive interests.
Is there anyone cooler than Elon Musk? The technology tycoon responsible for such gems as Tesla Motors and Space X (yes, a space transport company) has grown up in the public eye, transitioning away from boring hoodies and ugly t-shirts to top-notch designer clothing. In his media appearances Musk can be seen wearing sharp suits, leather jackets, designer jeans and aviator glasses. His style strikes a fine balance between wealthy entrepreneur and investor on the one hand and sophisticated scientist on the other.
Donald Trump’s hair has been a subject of great debate for years. Since becoming the frontrunner for the Republican Party in the 2016 primaries, speculation about The Donald’s signature helmet has taken centre stage. The canary yellow/tawny orange pile of fluff has become so synonymous with Trump that it has made the cover of magazines. Forget foreign policy, the shrinking middle class or immigration, what people really want to know is whether The Donald’s hair is real. Trump tried to settle the debate last year on the campaign trail when he asked a woman to examine his hair to prove it wasn’t a toupee.
Trump’s signature do is one of his most defining features. He appears unwilling (or unable) to get rid of it. Given his 20-point lead in the polls over his next opponent, there’s a distinct possibility that Trump will take his hair controversy straight to the White House.
 Forbes 400. #211 Mark Cuban.
 Sara Wilson (October 15, 2008). “Be Like Branson.” Entrepreneur.
 Dipal Acharya (September 18, 2014). “Dressing up with Richard Branson.” Evening Standard.
 Richard Branson (July 2, 2015). “Drop the dress code.” Virgin.com.
 Prifle In Style Series (June 26, 2013). Larry Ellison – A Profile In Style. JosephRosenfeld.com.
 Hucklebury (August 20, 2014). “Elon Musk Style [Entreprenuer].” Art of Style.
 Sebastien Blanc (January 28, 2016). “Trump’s hair has stylists shaking their heads.” Yahoo! News.
 Baker Machado (August 27, 2015). “Donald Trump Asks Woman to Examine His Hair to Prove He Doesn’t Wear a Toupee—Watch! Pop & Politics.