Dressing Like a Billionaire


“Clothes make the man. Naked people have little or no influence on society.”

– Mark Twain

The very idea of dressing like a billionaire is implausible to the point of being silly. Billionaires, after all, are not generally thought of as being particularly well dressed.

Warren Buffett, for example. He wears suits that seem to be bought off the rack at some Omaha discount store. His glasses say “These babies work!” His most prominent stylistic feature is the incredible growth that is his eyebrows.

Still, he doesn’t look all that bad. He looks like a rich guy who is comfortable dressing like a working-class joe. And that’s the image he wants to project. So good for him.

Steve Jobs was even more challenged when it came to dressing. His sartorial choices left him looking confused. Was he a boy or a man? Was he a visionary or a geek?

So why should you want to dress like a billionaire? The answer is that you shouldn’t. Your goal should be to dress well – really well – as well as you could if money were no object.

And, you will be happy to know, you can do that without spending a lot of money.

Why Bother?

If you have a billion dollars, you can dress like Warren Buffett and people will still respect and admire you. But if you have ordinary wealth (that is to say, not a lot), dressing well has its advantages.

First and foremost, dressing well makes you look better. If you are chubby, it makes you look slimmer. If you are short, it makes you look taller. If you are tall and thin – hell, if you are tall and thin (and young), you look good in anything. You can skip the rest of this.

Except that dressing well often makes you feel good. For me, what I put on in the morning has a lot to do with the way I feel about myself when I wake up. If I am full of energy and enthusiasm about the day, I take a bit of time to select clothes that please me. If I’m feeling down on myself for whatever reason, I select clothes that make me feel dumpy. (Why do I still have such clothes in my closet? Good question. I’m working on getting rid of them…)

The Fundamental Rules Apply

Many people equate dressing rich with designer clothing. But there is nothing more foolish, in my humble opinion, than to spend tons of money on designer clothing when you are living on a budget.

Another bad idea is “fast fashion” – cheap but very trendy outfits that can be bought at stores that have cropped up to serve the cheap-but-trend-following consumer. Fast fashion is like fast food. It’s inexpensive and it gives you a quick fix, but it is not necessarily good for you.

Another big problem is typically American: favoring quantity over quality.

There is a better way.

You can dress well and feel very good in your clothes without spending a lot of money. All you have to do is learn a few basic principles that will improve your wardrobe and save you a fortune spent on the wrong clothes.

Two Simple Rules for Dressing Well

A first-rate wardrobe can be yours for very little money if you follow two simple rules:

  1. Never buy anything – no matter whose name is on the label or how cheap it is – if it doesn’t make you look and feel good when you put it on.
  2. Buy quality clothing but don’t buy it at full price. Buy when it is discounted by at least 50% or buy it second-hand.

Whether you’re buying second-hand or brand-new (and on sale!), the trick, of course, is to know what you’re looking for:

* clothing that will last – garments that are very well made and classically styled

* clothing that fits you perfectly (or can be easily tailored)

* clothing that makes you feel as good as you look when you put it on

Put Your Wardrobe on a Diet

According to a poll conducted by Time magazine, men own an average of 12 pairs of shoes. Women own an average of 27 pairs of shoes and more than 10 handbags.

In this regard, I must confess, my feminine side prevails. I must have 40 pairs of shoes. To me, each one is different. But even my wife can’t tell the difference between one pair of black penny loafers and another. (“Can’t you see how much wider that band is?”)

This addiction to shoes doesn’t help me dress better. It is a hindrance. For one thing, I can’t see all of my choices just by looking into my closet. The shoes that end up toward the back get ignored for months or even years at a time. For another thing, the selection process is stressful. Had I fewer choices, I could make quicker and more confident decisions.

To dress well, a man does not need more than six or seven types of shoes. A woman will need a few more – but certainly no more than a dozen. (Don’t quote me on this. I’m generalizing. But you get the point.)

I used to have more than 60 dress shirts in my closet. A third of them didn’t even fit me. Another third were in colors that made me look half dead. I recently winnowed down my shirt stock to about 24. I like them all and they all look good on me. Selecting shirts is now a simpler and more pleasing process.

Right now, I have way too many pants – both casual and dressy. Sometime this week, I intend to spend 90 minutes in front of a mirror getting rid of half of them. Same holds true for my T-shirts, my golf clothes, and my belts.

Choose Quality Over Quantity

If you have never worn a quality garment, you may doubt that there is much of a difference. From a distance, a cocktail dress from H&M might look as good as one from Saks Fifth Avenue. But up close, the difference is obvious.

Seams and Hems. Stitches should be tight and close together, not loose or broken. Hems should be generous. If there’s a pattern on the fabric, it should line up neatly at the seams.

Linings. Skirts, suits, jackets, and trousers that are lined tend to be higher-quality garments. They glide onto the body easily and hang better than those that are unlined.

Reinforcements. Buttons, zippers, and pockets should be reinforced for wear. Pockets should be sewn to the lining. Zippers should be lined and invisibly set into the garment.

Fabrics. Wool, silk, cotton, and linen are always best. Sometimes newer garments will have a bit of synthetic mixed in for durability.

Trim. Synthetic lace is a dead giveaway that the piece is not well made. If the trim is skimpy, so is the cut and fabric. Plastic belts and base-metal buckles look like what they are.

By stocking your closet with quality clothes, you enjoy several benefits. You will have the comfort of knowing that they are all well made. That, I’ve noticed, actually feels good. You will also have the economic benefit of endurance. Quality clothes last longer than inexpensive knockoffs. Often, they last five times as long.

Price vs. Cost of Use

There is a big difference between price and cost of use. Price is the initial expense of purchasing something. Cost of use is how much you actually pay over the lifetime of possessing it.

Here’s the problem. When you shop all the time and buy cheap things, you spend a lot of money on a bunch of stuff that you’re not going to want to own long-term. So when you do run across a good buy on a quality item, you’ve already blown your budget. Basically, you’ve thrown your money away.

So instead of tossing $20 here and $20 there, save it up. When you put on a garment made of great fabric and it fits well – it just feels different. It will be a piece you will want to keep and wear again and again because you will feel good in it. And it will be cheaper in the long run.

Choose Natural Over Synthetic

Clothing manufacturers have done wonders with synthetic materials. They are easy and inexpensive to make, and can sometimes resemble natural fabrics.

But natural fabrics have natural advantages. They tend to work better in terms of heat and cold. They have characteristics that make them distinctive and memorable. And they last longer without looking shabby.

So start thinking of your wardrobe as an investment – not as a disposable part of your life.

Classics – the Foundation of Your Wardrobe

People known for their taste in clothing have learned what works for them. They have figured out what to include in their wardrobes – and, just as importantly, what to leave out.

They are suspicious of fashion trends. They understand that when you follow a trend, you tell the world that you are a sheep and not an individual. They favor classical pieces, but they are not afraid to experiment with bits and pieces that make their particular style of dressing unique.

My feeling is that 80% of your wardrobe should be classics… items that you can keep for 10 years without worrying about them going out of style. The other 20% should be items that define your personal “look.”

What makes the classics so valuable as the foundation of your wardrobe is their simplicity and elegance. They are timeless for a reason: You can wear them again and again, making them look different simply by changing your accessories. And the image that you present to the world will always be positive.

Tips for Men

No matter what your lifestyle is, there are several things that every man should own. These are the basics:

1 suit

1 blazer or sport jacket

3 ties

2 pairs of jeans

1 pair of dark slacks

1 pair of chinos

4 dress shirts

4 sport shirts

1 pair of casual shoes

1 pair of dress shoes

12 pairs of socks

1 trench coat

If you own only one suit, make it a dark color. Black, gray, or navy in 100% wool is the most versatile.

Your basic dress shirts should be solid white or blue in a cotton fabric that is easy to launder.

For your dress shoes, choose a pair of black lace-ups. For your casual shoes, choose a pair of loafers in brown or black.

Good socks are essential. They should cushion your foot, not ride down or bunch up.

Dark trousers are fairly formal and can be paired with a classic navy blazer or sport jacket. Chinos are more casual but dressier than jeans. As for jeans, go for a dark wash that will look good with either a dress shirt or cotton T-shirt.

A classic navy blazer will look sharp with the dress slacks, the chinos, or the jeans.

Tips for Women

Women tend to have way too many clothes. And in spite of that, they often stand in front of the closet in despair, thinking they have nothing to wear. The answer to this problem is to start with a core wardrobe of neutral-colored classics, and build from there. Your core wardrobe might include:

1 pencil skirt

1 “little black dress”

2 pairs of jeans

2 pairs of dress pants, dark and light

4 blouses

4 casual tops

3 sweaters

1 jacket

2 pairs of casual shoes

1 pair of dress shoes

1 trench coat

The idea is to dress to emphasize your assets and cover up your figure flaws. So, for example, if you have a short neck, you’ll want to choose V-neck tops to elongate your neckline. If you have great legs, you’ll want to wear short skirts to show them off.

A pencil skirt is flattering on almost all body types. So are single-breasted coats and jackets.

When shopping for jeans and casual pants, here are a few guidelines:

* straight leg – looks good on everyone

* wide leg – good on women with big bottoms and fuller figures

* boot-cut – good on women with long legs, pear shapes

* narrow leg – good on women with slim legs, petite frames

For your dress shoes, choose a pair of black pumps. For your casual shoes, choose ballet flats and/or loafers.

For your jacket, choose one that can be paired with the skirt, the dress pants, and the jeans.

And be careful with the bling. Too much looks gaudy no matter how expensive it is. Classic equals understated.

Finally, few words on the subject of black. Black is figure-flattering. Black is elegant. Black is timeless… and always a good choice.

Make It Fit

A skilled tailor is the secret behind many people who consistently appear on “best dressed” lists. He understands different body types and knows how to make yours look a little taller and slimmer by taking a tuck here and a tuck there. He knows exactly how long a skirt, a pair of trousers, and a sleeve should be. And a good tailor will tell you when something is not worth the money it would take for alterations.

Even an expensive garment can look cheap if it doesn’t fit well. And a moderately priced garment can look expensive when it is tailored to your body.

Taking Care of Your Investment

In 1997, Sotheby’s sold some of the belongings of the Duke and Duchess of Windsor. The collection included clothing that had been made for the Duke in the 1920s… that he still wore well into the 1970s. This speaks not only to the quality of the garments but also to how well they were taken care of.

Here are a few tips to keep your clothing looking as good as it did the day you bought it:

Brush suit coats, dresses, skirts, and trousers after each wearing. This takes about 30 seconds and will really make a difference in how long the garment lasts. A clean brush with stiff bristles will remove dust and dirt before it can settle into the fabric. Give it a good brushing and let it air out overnight before putting it back in the closet.

Make repairs as needed. If you notice a loose button, fix it before you lose it. If you notice a small tear in a seam, mend it before it gets any bigger.

Ditch the wire hangers. About the only use for a wire hanger that I can think of is to open a car door if you lock your keys inside. It certainly isn’t something you want to hang a $300 jacket on. Invest in wooden hangers that are least one inch thick at the shoulders. It’s a small price to pay.

Have wool garments professionally cleaned. Moths love wool. And they can eat it to shreds. Never pack wool clothing away without having it treated for storage. If the chemicals are objectionable to you, find a cleaner who uses a natural process.

Spend Time, Not Money

Like I said, the foundation of your wardrobe should be classics – timeless garments that you can wear for years.

Think about it. Even if you spend $400 on a beautiful wool suit at a consignment shop – and another $100 or $150 having it tailored perfectly to your body – that suit is a bargain. You’ll be able to wear it for at least 10 years. And every time you do, you’ll look and feel like a million bucks. Compare that to a $75 piece of crap that you might wear a handful of times… or not at all.

Pay attention to quality and fit. Make sure that you love everything in your closet. If you put something on that makes you feel less than great, get rid of it. If you try on something in a store that can’t be tailored to your body, don’t buy it.

Personalize your look with accessories – high-quality shoes, scarves, bags, and jewelry that define your personal style.

Every time you get dressed, you should feel like you couldn’t look any better even if money were no object.