Many of us are familiar with high producing sales people and most of us know that how they dress affects the bottom line in terms of sales, or at least that is probably what you have always been led to believe right? Successful sales people wear expensive suits, jewelry, shoes, you name it, but it’s not limited to just direct sales; its customer service, small business owners, executives, they all dress sharp because they are representing the company and how you dress is how the company will be seen. This has been what we have been led to believe for years and at one time it was without a doubt true, but is it still? I don’t believe so.
In the late 90’s I did a lot of work for public companies and I was constantly flying to New York to meet with executives of various companies. In 2000 I went to New York to watch the Yankees and the Mets in the World Series, and while there I was supposed to meet with an existing client on a marketing promotion that I had quoted him on; the deal was supposedly closed, I was simply stopping in for a quick hand shake and to sign the agreement. I didn’t bring any dress clothes because I was there to watch baseball not work, and this was just a quick meeting with a client that I knew well. So when I got to his office in the Financial District to “quickly” sign the papers for the deal we had already agreed on I was wearing Levi’s, a t-shirt, a leather jacket and a leather hat, he advised me that there was a minor hiccup and that before the board would approve the deal they wanted to see me. So I said sure no problem I don’t mind doing that, and he suggested I run back to my hotel to change my clothes and come right back; but I told him I didn’t need to change my clothes because I didn’t have any work attire with me. He had a real problem with me addressing the board of this public company in jeans and a leather jacket, and my response to him was, they are not buying my wardrobe, they are buying my expertise which remains the same regardless of what I am wearing. So I went in and talked to the board and at the end of the day they signed off on the meeting in spite of what I was wearing. This actually became the subject of jokes for many years because I showed up to this meeting with the board of directors of a public company in jeans and a leather jacket.
I know so many businessmen today that wear Levis, ball caps, and they close big deals; I had a friend from New York one time meet with the CEO of a public pharmaceutical company wearing jeans and a shirt that said “BITE ME” and he signed the contract that day. My feeling is if someone wants me to wear different clothes that what I have on, then they are not really looking to do business with me, but who they think I should be, so what I am wearing really shouldn’t make a difference. Today you have young billionaires running fortune 500 tech companies, marketing companies, and social media companies that have never put on a suit and tie in their life and they are very successful CEO’s.
It used to be said that dressing for success makes people more productive, I don’t believe that to be true, I believe dressing to be comfortable is more effective than wearing a jacket and tie. I have often been told that as a CEO that I should dress in a particular way because I am representing my company, and that how I dress is a big deal. While how I dress may be a big deal with some clients, I believe they will get over it; they are going to have to if we are going to do business together. I personally would much rather do business with someone who is comfortable with themselves rather than with someone who thinks that putting on a tie or upscale clothing is going to put my mind at ease, no I would much rather do business with someone who shows up being themselves, and that is what you get when you do business with me, the same person that shows up for a Saturday afternoon barbecue is the same person that shows up to a meeting with a client. The topic of conversation may be different, but I am the same person in either case and I think that most of the business world is slowly but surely gravitating to this mentality. I don’t feel like I need to dress like Donald Trump to be successful.