How to Dress Like a Billionaire

Dressing Like a Billionaire

Only a small handful of the world’s billionaires enjoy the public spotlight. Those that do give us a glimpse into the fashion trends of the wealthiest 1%. Some billionaires make their own fashion rules, but most like to fly under the radar.

According to 2021 market data from Forbes, there were 724 billionaires living in the United States. China is a close second with 698 billionaires, but the United Kingdom has only 56. You might imagine that someone who can afford the most expensive yachts and private planes to wear the most expensive clothes, but that usually isn’t the case.

There’s an odd style contradiction among some billionaires. On the one hand, they can afford to spend tens of thousands of dollars on wristwatches. On the other hand, they seem to enjoy being thrifty when it comes to everyday wear. It’s an odd combination of shabby chic that you can pull off, too.

A Closer Look at the Style Trends of the World’s Wealthiest Men


Shoes say a lot about a man. It’s one of the only fashion items that people use to automatically make qualifying decisions about a person. Normally, if your shoes are old and worn, then people assume that you’re a low value man.

That framework goes out the window when it comes to billionaires. They don’t spend a great deal of money on shoes. Billionaire men want comfortable shoes, and their choices are usually drab and unassuming. There are exceptions to the rule, of course. You won’t catch Lebron James or Jay-Z rocking a turned-over pair of shell top Adidas.

For the most part, a billionaire doesn’t depend on shoes to enhance his style. Ironically, the billionaire shoe has become a style piece all its own. Just check out these Ned Flanders shoes from Adidas. They sold out in most retail outlets almost immediately. Get yourself a pair (if you can) to rock out like a boss.


A wristwatch is a powerful accessory. Similar to shoes, a watch can instantly qualify a man’s personal taste. There are cheap watches and expensive ones. However, the wealthiest men tend to always choose expensive ones.

There’s a genuine appreciation of the craftsmanship of a beautifully made watch, but it goes deeper than that. There’s an exclusivity at play here. This is one of the only areas of style where a billionaire might show off the extent of his wealth. The Patek Phillipe Nautilus is a holy grail wrist piece. A rare Patek Nautilus recently sold at auction for $470,000.

Even though watchmakers like Patek Phillipe are the upper crust of wristwear for the elite, there is still nothing like a Rolex watch. It’s one of those fashion accessories that indicates you’ve “made it”. Get yourself a high quality, genuine Rolex and you’re on your way to looking like a billionaire.

Related: Here’s Why Rolex Watches are so Popular


Outerwear provides the billionaire man with a chance to showcase his personality. Sometimes, it’s a bit of a reach. Some billionaires wear rugged jackets to try and look tough even though they haven’t hiked a trail since before their stocks took off.

Don’t be overly pretentious in this category. Choose outerwear that’s well made and upscale. Avoid big brand labels plastered across the back or gimmicky zippers and pouches. Think about the recreational activities of a billionaire and go from there.

Barbour is one of the finest companies producing men’s outerwear. Their wax jackets might last a lifetime under the right conditions. You might recall that Daniel Craig wore a Barbour hunting jacket in the film Skyfall.

The top of the range Barbour jacket costs £400. You can gain entry to the Barbour jacket club for as little as £100. What makes Barbour jackets fit for billionaires is the focus on long-lasting materials and high-quality craftsmanship. Both factors are qualities that the top tier earners of the world admire.


Billionaires don’t fuss over their trousers. You rarely see billionaires in the public eye wearing big name designer jeans that cost a lot of money. This is one of those areas of a billionaire’s dress code where less thought equals greater peace of mind.

That being said, billionaires don’t look shabby in their trousers either. They might buy several pairs of the same make and cut or go for whichever trousers offer the highest level of comfort. You can rock the billionaire look too with a pair of jeans or trousers that are clean and comfortable. For extra points, avoid any semblance of trendiness and rock a pair of mom jeans.

When wearing trousers fit for a billionaire, avoid loud colors and patterns. Monochromatic tones are the quintessential rich guy choice. Richard Branson is a style icon but check out how he wears his no fuss trousers in this Instagram pic.


Fashion tops for men are somewhat of a freestyle category for billionaires. Some will shamelessly promote their products, brands, and services with T-shirts while others choose simple white or black button-up business shirts.

You could never show up to a business meeting in a black T-shirt unless you were the CEO of the company. So, exercise a bit of caution when it comes to choosing your billionaire top. Business casual is acceptable for everyone.

Formal Wear

A formal suit for a billionaire is reserved for special occasions, shareholder meetings and hosting heads of state. Truly, you rarely see billionaires in formal attire when it’s a professional setting. That’s mainly because they don’t have anyone to impress in the office and they’re the ones at the top of the food chain.

Most of the time, it’s business casual. One of the best things about formal wear for men is that a black suit or tuxedo is a great equalizer. You can look just as classy as a billionaire with the right black on black ensemble.

Zara has a nice selection of affordable men’s suits. Opt for a black coat with matching trousers and then pair them with a black V-neck vest and black shoes. Just make sure that the fit is spot on. Nail the look and you’ll fit in with the top movers and shakers of the world.

Related: Here’s Why Dress to Impress is the Best Style Advice for Men

The Takeaway

A billionaire is rarely the best dressed man at the function. You really need to evaluate a billionaire’s style on a piece-by-piece basis. Put all the items together and you’ve got a hodge-podge of fashion faux pas that are only canceled out by their extensive wealth and prestige.

If you care too much, then you’ve missed the mark. Dressing like a billionaire is all about blending comfort and inconspicuousness with sprinkles of premium style pieces that only the wealthy will recognize.

If you truly want to emulate a billionaire, then its best to study the thoughts and actions that helped them achieve success. Then, you can afford to start your own fashion trends. It’s understandable if you’re a little way out from hitting that mark. For now, just keep it classy in your Ned Flanders sneakers.

Read Next: 5 Style Mistakes That Older Men Make


About Freddy Blackmon 226 Articles
Freddy Blackmon is a freelance writer and journalist who has a passion for cars, technology, and fitness. Look for articles on these topics and more. Follow him on Facebook and Instagram.