How To Dress Like a High Net Worth Individual

There are 3 ways to look like a billion bucks.
IMAGE Warner Bros. Pictures

How Does One Dress Like a Rich Person Exactly?

Sometimes, it's not about what you have in your bank account, but what you have on you—as in your clothes. Dressing like a rich person isn't about covering yourself up with designer duds and gold chains. It's about the attitude.

1 | Dress like you don’t care

Sometimes, the man in the most stylish suit is not the one with the fattest bank account. Example: the Billionaire Who Does Not Care wears the random free T-shirt, a pair of faded khakis with legs that look like limp balloons, and anything shoes (maybe slippers). He is devoid of style, and for him, its okay because he has no one to impress and nothing to prove.

Or, maybe he has more important things to do. Recall the reply of Facebook overlord Mark Zuckerberg when asked why he wears the same gray T-shirt all the damn time: “I'm in this really lucky position, where I get to wake up every day and help serve more than a billion people. And I feel like I'm not doing my job if I spend any of my energy on things that are silly or frivolous about my life.” While we never think style is silly, we are onboard with uniform dressing. If you’ve found a style that works for you (and helps you make more money), why not? 


2 | Dress to impress

If you’re a man who has come upon his fortune recently, the desire to announce your arrival will tempt you to literally wear money on your sleeve. Flash, gold, luxury logos—all at the same time. Don’t do this. 

Instead, do it like the fictional Jay Gatsby, who after making his fortune, wore only daring suits but still looked dignified. See 2013’s The Great Gatsby, where Leonardo DiCaprio as Gatsby wore a three-button dinner jacket with gauntlet cuffs, a white linen suit with silver shirt and gold tie, and a three-piece linen suit in soft pink.

How’d he do that? It helped that Catherine Martin was the film’s costumer, so all the elements of Gatsby’s wardrobe, from the straw boater with navy grosgrain ribbon on his head to the two-tone spectator shoes with the dark brown vamp on his feet, was well-thought out (note how the dark colors of his accessories bookended the pink look.) 

We can’t all have the swagger of Gatsby or an Oscar-winning costume designer to help us, but we can be bold with a knockout suit that has the right details.

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3 | Dress like you’re on perpetual vacation

A cardigan in soft leather. A crewneck sweater in crepe cotton. A pair of narrow trousers that is the dust-colored. This is the sweet spot. The clothes are soft. The look is louche. The feel is very, very comfortable. The effect is stealth wealth, and it’s hard to pull it off.

When executed poorly, this casual feeling can lead to Guy Who Just Rolled Out of Bed. To do it right, adhere to old money style codes: classics in neutrals with excellent fit. That means a white button-down, gray shawl-collar cardigan, unlined blazer, or a navy trouser. Also—and this is important—only shop quality clothing. Nothing says wealth than loungewear that transmits polish.

One more approach is to break the rules. Fiat king Gianni Agnelli, one of the most stylish men that ever lived, is the perfect example of the unstudied look. He wore loafers with suits, ties that were always askew, and his watch over the cuff of his shirt.

We don’t suggest trying that last one (only a style god can pull this off), but we do encourage injecting a bit of devil-may-care attitude in how you wear your clothes.

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Clifford Olanday
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