Think it really matters how you dress? If you’re an overall good person, shouldn’t people realize it and not judge you based off your threads?

Well, I hate to be the barer of bad news, but people judge you based off of the clothes you wear. I don’t care if you’re walking down the street, or sitting in a business meeting; people are constantly looking at what you’re wearing.

Over the past 10 years I’ve dressed like a bum, worn decent clothes, and dressed like a boss. I must admit, there is a huge ROI in wearing nice clothes… especially in the business world.

The Bum Years

When I first started out as an entrepreneur I didn’t have much money. So whenever I went out to networking events I either wore baggy jeans that looked like I had poop in my pants or slacks and a shirt that typically didn’t match. Most of my threads were from Target.

As you can probably already guess, half the issue was that I had no sense of style and the other half was that I didn’t want to spend too much money.

Whenever I walked into meetings or went to a conference people wouldn’t really give me the time of the day until they got to know me. Once they learned I was somewhat smart they were willing to listen to me and potentially work with me. The issue was, it took people a while to warm up to me because no one wanted to waste their time talking with someone who looked like a chump.

After a few years of going through this, a friend of mine kindly suggested that I spend a bit more money on my wardrobe, pay more than 10 bucks for a haircut, and get a decent pair of shoes.

I invested two thousand dollars in making myself over. And boy, it made a huge difference…

Note: During this phase of my life, my hourly consulting rate was under $100.

My big break through

With my new clothes, a somewhat decent haircut, and nice pair of black shoes I made a break through. At first I noticed that people were more willing to talk to me when I went to conferences. I also noticed that during my business meetings people took me more serious.

However, none of those things really mattered because they weren’t big breakthroughs.

What was a big break through was that people assumed that I was somewhat well off because I was dressing much better. When I starting talking to potential customers they naturally assumed that I was successful and my services were costly because I was better dressed.

So when it came down to locking in new deals these potential customers started offering me more money. As I got a taste of money making, I wanted more, so I decided to take things up a new level with my wardrobe.

Note: During this phase of my life, my hourly consulting rate went up to $250.

The Boss Years

From Gucci suits, to designer shoes, to 5 figure watches, I stepped up my appearance as much as I could within my financial constraints. And boy, not only was there a huge ROI, but it was a much bigger difference than I ever experienced between my bum and normal stage.

By dressing to impress, successful business owners started to flock to me when I attended networking events and people listened when I spoke in business meetings. In addition to that I was praised for wearing rare watches that other business owners wanted, but didn’t have.

This experience taught me that successful people like to hang around with other successful people as they tend to feel comfortable around themselves. Now, by no means am I saying that all successful people dress nice, but the chances are if someone comes up to you and they are wearing a 5 figure watch, they have money.

And when you start talking about business with these successful people, they know that if they do business with you, it’s going to be costly for the following reasons:

  • You have an expensive lifestyle – if people realize you have money, they know that they are going to have to pay a pretty penny to work with you. They know that if you throw around small amounts of cash in front of you, you just won’t care.
  • It has to move your needle – in business there is saying that if it doesn’t move your needle, it’s not worth doing. So if the amount someone is willing to offer you isn’t life changing, there is a much greater chance that you won’t accept it. Due to this business owners will throw out much larger amounts if they want to work with you.

By dressing like a “boss” my credibility went through the roof with other business owners and I was able to do things like close 7 figure business deals.

Note: During this phase of my life, my hourly consulting rate was above 4 figures.


Although you should dress to impress because there is an ROI, there are a few caveats that you ought to know about.

The first is that if you aren’t clever dressing to impress won’t work well for you. People will see right through it and you won’t build any valuable business relationships. So before you go out and start spending money on clothes and watches, make sure you know what you’re talking about.

The second thing that you need to know is that after you have “made it” and people know you’re successful, it doesn’t matter how you dress. Although I still feel I have a long ways to go in my career, most people see me as being successful.

These days I wear sneakers, cheap t-shirts, and I don’t really sport fancy watches because I want to focus on work. That stuff was never me, and although I used it to get further in my career, I still prefer shopping at Target over Nordstroms.

In the short run, dressing to impress is definitely worth it, but you also have to make sure that it doesn’t get to your head.

You can quickly start spending thousands of dollars on clothes and after a certain point, there really isn’t a big difference between a thousand dollars on a suit versus spending five thousand.

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