Does How You Dress Make You More Money?

By on Oct 13, 2016

I worked in my father-in-law’s independent insurance agency in the Washington DC area from the late 70s through 1990. At that time (and I think it continues today), Washington was a very formal city. I never came to work without a suit and tie because that was expected, and you never knew when you would need to see a client.

In 1990 we moved to the Fort Worth, Texas, area where I sold commercial insurance. The “dress culture” was very different from Washington. If I would show up wearing a suit and tie, the prospect would think I was from the IRS. My days in Texas taught me that business casual could work just fine. Even so, I always tried to dress up a bit more.

A popular book in the 70s was John Malloy’s Dress for Success (updated in 1988). He argued that first impressions are very important and that what you wear does make a big difference in how people initially perceive you.

Today, business attire, in general, is much more informal. While there are a few cities where more formal attire is expected (Washington DC, New York City, Boston?), business casual seems to be the norm in most places. This is particularly the case in the online and tech world where T-shirts and shorts are the norms. “Who cares how I look if I can get the job done.”

My awesome bow tie!I do find it interesting that when I wear a bow tie during a presentation, I tend to get more comments from people on how much they like the look. I am not sure if it makes me look professorial or not, but it certainly helps me stand out. It’s interesting to me that the simple addition of a bow tie changes people’s perception.

So, does how you dress make you more money?

I came across an interesting article written by Neil Patel titled How Spending $162,301.42 on Clothes Made Me $692,500.

One of the key points in this article is “People believe what they see. If people think you look successful, in their eyes you are successful.”

I have noticed a few insurance agents over the years who project success. I realized part of their demeanor was confidence and the other was the way they dressed. Their nice looking clothes projected success.

I am going to start an experiment of my own. As you read this, I will be flying to New York City for a presentation on Friday morning. Based on the recommendation of a friend, I have scheduled an appointment for a fitting at Proper Cloth. They make custom shirts. Once they determine my proper shirt size, I can order online anytime and have my custom shirts shipped directly to me.

While I could do the fitting online (it’s an easy process), I decided to have a personal fitting simply because I was going to be in the city. Their shirts cost about twice as much as what I would usually pay from Lands’ End (my current provider of dress shirts).

Will it be worth paying for a custom fitted shirt? I’m not sure yet, but I’m certainly willing to give it a try.

So, what do you think? Does how you dress make a difference in your income? Or, is business casual just fine? Let me know in the Comments below.


  1. I may be old school (baby boomer) but I believe dress makes a difference in income in that you project yourself differently when dressing professionally by projecting confidence.

    • Some of this conversation is old school, but that does not mean there is not something others can learn from. People want to deal with people who are successful. If you look successful, you are perceived as successful.

  2. Hi Steve,

    I agree,… people believe what they see. Like you, I put on a bowtie most days. There isn’t anything that says I have to. I am known all over town as the guy who wears a bowtie. It makes me feel good and successful. Everyone should take some pride in how you look when you walk out the door in the AM.. It sets up the day….

    PS- I bought some custom shirts from
    I love them,….. Money well spent

  3. When I first got into the life insurance business in 1979 a coat & tie were the norm. As time went by, I was in a conference and a speaker was talking about this subject (I wish I could remember his name), and his observation was the one step up approach. He felt that an insurance salesperson needed to dress one step above the culture of the client. If a farmer, nice casual slacks and button down. If a businessman, sport coat & tie, if an attorney, cpa, banker or any other white collar professional dress the best you have. Even today, I try to follow that principal.

    • Scott, I agree. That was the principle I used in Texas. I did not always wear a coat and tie, but I did try to dress “one step up.” Thanks.

  4. Hi Steve,

    I work in a suburb of Dallas, Texas and I agree with you that business casual is the norm in the business world these days. However, there are levels of business casual if you know what I mean. Most of the men have the same level of business casual…slacks and a button up or golf shirt. The women have MANY levels. I’ve noticed that women in higher roles and therefore making more money, tend to dress on the nicer end and look more put together.

    I enjoy casual Friday like anyone else, but I still wear my nice jeans with a nice blouse and/or jacket and nice shoes. It makes me feel more professional and ready to interact with my customers. Some people wear jeans, a t-shirt and tennis shoes. That makes me feel ready to go shopping. No offense to those who are just as ready to work as I am.

  5. My mother always taught me to “dress for the job you want and not the job you have.” My mother is always right.

    Good appearance to our customers shows that they are important enough for us to look our best.

    Mentally I have always found your performance mirrors your appearance. If you are prepared and look good your performance will be reflected in that effort.

  6. When I first went into the insurance business with Federated Mutual – every male whether in the home office or in the field (my area) was required to wear suit and tie – the females were to dress in dress’s or suits – except in the Minnesota home office where during the winter – pants suits were allowed. When I went into the agency operation my compatriots were a bit more casual – but still wore shirt (open collar) dress slacks and of course shoes that were shined like a mirror. It was when I developed the niche that I currently enjoy that I went to tailored dress shirts with the agency logo on them and that’s where I am today….logo shirt, dress slacks, penny loafers. I miss the opportunity to see you at conventions (AIMS) but I don’t believe that group has them as frequent as they used to. Regards. “MO” Greenwood – Insurance Group of Junction City, Kansas.

  7. Hi Steve,

    I read Dress for Success when I first graduated from college and agree whole heartedly with the concept. Certainly location has much to do with what is acceptable or appropriate, but dressing professionally sets the stage for a client you are looking to impress. It makes a statement about how you see yourself as well.


  8. great article! I think it depends on the client audience and how I dress is shaped by that. Things have indeed changed for the 1980’s where coat and tie was required. Casual Friday has morphed into casual everyday!

    • Jay, yes, it does depend on the audience. And I think it is a worthwhile conversation given the casual nature of younger people.

  9. It depends on your audience. If I’m meeting with a boomer for their personal insurance, I’ll wear Khakis, a long sleeved shirt loafers, and a sport coat. I add a tie for most commercial account meetings. Millennials, Gen X & Y, I skip the jacket so I don’t look too much like their dad!

  10. I have read many dress for success articles over the years and find them very interesting. The only downside I have seen is in the case of working in a small town. Dressing well can sometimes result in comments such as, ‘they must make a lot of money if they can afford so many clothes’ .

  11. I agree that your dress reflects your professionalism. It even affects your self image. On days that I dress less professionally, I FEEL less professional. I have heard many young women complain that their clients do not view them as being a professional. If they would take a candid look at their attire, I believe they would understand why.

  12. Hi Steve,
    I think that dress and grooming are very important. It’s important for your image with your clients as well as for your own self image. I think that you act more professionally when you are dressed professionally. I wear a tie in my agency in Sarasota, FL and will expect my employees to dress the same way as I hire them.

  13. I am also an old school baby boomer and appearance has always been important to me. Even when wearing “business casual” I take it up a notch. I have found over the years that I am treated with more respect and I believe it is because of appearance. Time and time again studies have proven that appearance does make a difference in how you are treated and in getting ahead. I am appalled at what some people wear in the workplace. I wouldn’t wear some of the outfits on a weekend at home!

  14. My father always told me: “Dress not for the job you have, but for the job you want.” So, I like your approach with a dress shirt and bowtie. You look good. 🙂 And while all the younglings were t-shirts, it is good from time to time to show them how a real, classy a man should look.

Submit a Comment

Your email address will not be published. Required fields are marked *