I was in a seminar with people from different fields outside of real estate and I loved hearing their stories as they brought new perspectives to the room about sales. One of the topics we hit on was grooming or dressing for success. I want to relate a story that I found quite interesting and has stayed with me for years.

A good-old-boy, third-generation farmer from a long-established family in Ontario’s former tobacco country wanted a different career and had the desire to get into financial planning.

He thought it out and then went from farm to farm to see all his relatives and other people that were intertwined with his family for generations. He drove in his pick-up truck and wore his jeans and baseball cap. For six months, he called and called and didn’t make one sale.

In despair, he went to a family friend, a Dutch uncle, and asked him to tell him honestly what he was doing wrong.

Story continues below

The old-timer said, “You come in looking like us, acting like us and you are one of us. Problem is, we don’t want one of us, we want a professional.”

The man thought on it long and hard. He decided to make a change. He borrowed a friend’s car and started wearing his Sunday suit and carrying a briefcase. Slowly, he started to make sales. Eventually, the sales grew into a very successful business.

A very interesting story. I know that many of you believe that you can sell real estate wearing jeans and a baseball cap, and I acknowledge that you can – for the short game. But for the long term, the lesson this man related shows that being a professional is about image, about being your own brand, of dressing for success.

Are you projecting a professional image at all times or are you just “one of us?”

Barry Lebow, FRI, Master-ASA, ABR, SRES, is one of Canada’s most recognized real estate authorities. Now in his 51st year of professional real estate, Barry has been honoured by many real estate associations for his work in the profession. He has testified in more than 500 trials across North America. He is the founder of the Accredited Senior Agent designation program. A teacher, trainer and educator, he is a broker at Re/Max Ultimate Realty in Toronto. Contact Barry by email.


  1. About writing off our clothes, funny story. I ran a small brokerage. Within ten days, I got one suit hit with wet paint (guy was painting on a ladder and spilled) and another ripped on a nail. I bought two new suits and put them through the business. A year later I was audited. Actually called into (back then) Revenue Canada’s offices and they started hammering me about these suits and that I could not. I explained that I needed suits for my work. Then one guy said, “well, it is not a uniform.” I then asked for a definition of a uniform. They brought out the Act and I smiled. I took out a black piece of paper, wrote down, “I hereby direct every person on staff at Lebow Realty Ltd. to wear a navy blazer, tie of choice, white shirt, grey slacks and shoes of their choice. This shall be the firm’s uniform” and then I slid it across the table to the feds. They went into a frenzy. They called in supervisors, then others. Calls were made, this went on for almost 2 hours. Finally, some said that did constitute a uniform, other did not. I made a deal with them, they raised my car expenses to 90% write off and I gave up on the suits. I left smiling.

    • Barry:
      I am deep in the throes of dealing with the Rev. “suits” right now.
      Dec. 23rd last I received a re-assessment notice from one of their suits stating that I owed $5,103. from 2009 and 2011 due to unfiled GST/HST returns.
      I challenged them over the phone and said that there was no way that I owed that much even if I had not filed. I was sure that my accountant ‘had’ filed said returns, and furthermore, why had they waited so long to let me know about this alleged failure to file, letting interest arrears charges and late filing penalties build up without my knowledge and opportunity to address their claims years ago. I was directed to pay up immediately or else legal action would result per their letter. I told the agent who I had on the phone to tell his superiors that I would see them in court. I told the agent that I hoped my call was being recorded, because I was paying them nothing. “They can take me to court and thence to jail before I will pay them one red cent!” I stated. the agent said that he would pass my message on.
      My accountant later that week re filed for those two years. He said that he might have overlooked filing for those two years, but that nevertheless, I owed only $270.09
      Just last week I received via snail mail another re-assessment notice from Rev. Can.
      Now they only want me to pay $532.07 including arrears and a failure to pay penalty.
      I deducted the arrears charges and the penalty and wrote a cheque for the difference ($270.09). I folded it up (their written directions say “Do not fold cheques” and stuffed it into their return envelope complete with a letter explaining why I was not paying the charges. I put it in snail mail with a smile.
      Waiting to receive the next directive from one of their suits.

  2. I always just “felt” more business-like when I wore a dress shirt and tie in some previous careers. Conversely, whenever I went into the store wearing jeans and a t-shirt, I did NOT feel the same, and other people looked at my differently. (Plus, I’ll never forget the bit of a “swagger” I had when I bought a new suit and wore it into the office for the very first time or two. Almost empowering in a way) Depending on the situation, I still wear a dress shirt and tie on occasion
    , and get (mostly) positive feedback.

  3. Bravo, Barry!
    While leaning toward the point of the article, I must say I find the issue to be more about common sense than absolutes. Perhaps a generous helping of respect for those we serve would be a better guide than what one might find most convenient for oneself on any given occasion.

  4. Business professional is the only way to conduct yourself imo. Wearing shorts to an appointment is akin to showing up to the rink without skates and a stick.

  5. There is a fine line. Any imbecile can rent a fancy suit, but you can’t rent credibility. If the client grasps, (and they will, quickly,) that the fancy suit you’re wearing is an attempt to camouflage your ignorance or inexperience, you are no farther ahead.

    Would I dress like a bum? No. Attempt to impress with my clothes? No.

    If you know your clients, you’ll know how to relate to them effectively, and that includes how you dress.

  6. To begin with, proper dress affect the wearer. If you dress nice, you feel nice. If you dress professional, you feel professional. If you feel professional, you act professional. For most it will be difficult to take seriously someone who is dressed in a baseball cap, shorts and sandals, unless this person works in the Caribbean and is wearing bermuda shorts.

  7. As an agent, I find that as the relationship progresses, and Iget a feel for the client, I can be a little more relaxed in my dress – depending on circumstances. I will occassionally wear jeans if I am showing acreages, or land only and have to walk in mud etc., or it’s a short notice and I was out running errands at the time. But other than that, I will wear dressier clothing because you never know who you’re going to meet when you’re out and about.

  8. I have always felt this way too, but lately I’m starting to wonder if the world is changing. Do the Millenials feel the same way as the boomers? They work at companies that install slides to move floor to floor, they have “creative rooms” at the office (we used to call them break rooms – used strictly for smoking, coffee and gossip!) Are they still looking to the suit and tie as a symbol of the professionalism that we stand for? Or are they looking at the confidence that comes with jeans, skinny or otherwise? They still have liquid lunches but now it’s fruit smoothies, green tea with sushi, craft beer samplers. I believe that professionalism is important, but I think this new generation is looking to find it in deeds, not in dress.

    • good point! “Our” world is not “their” world anymore. Steve Jobs wore jeans…but I too must agree that image is important. Maybe it depends on who the client is? Or their age bracket?

  9. Jeans and baseball cap, not cool. Shorts and sandals is much better.

    And by the way, it’s called “real” estate because it is the king’s estate… not because it is tangible. Real comes from Re and means King. So in essence, you are buying a taxable equitable title, not genuine personal or private property.

    • I like the image “Shorts and sandals” and I know of one very successful Agent that works that way and has done so for a good number of years. However, in the winter he tends to wear long pants, but he still wears sandals, but, in the winter he wears socks too.

      But as for my personal opinion, the writer is “bang on” when it comes to image. Over my 40+ plus years of selling Real Estate, I have had more success when I dressed the part.

      God bless you;


      • Amen! Barry is Bang On!!! We owe it to the buyers and sellers who become clients professionalism in every aspect of our business: Attitude, Ability, Compassion, Understanding, Appearance including grooming and dress.


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