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Entrepreneur Dress Code: Can You Wear a Flannel Shirt in the Boardroom?

Unless you are directly involved in a small minority of high-tech businesses and Mark Zuckerberg was your college roommate how you dress really does matter.


[pullquote align=”right”]”The simple answer to the question of whether you can wear flannel in a boardroom is: Yes. However, what you wear and why you are wearing it can have an effect on the outcome of your meeting.”[/pullquote]Just recently, I walked into a board meeting wearing jeans, a flannel shirt, and boots. The room was filled with a mix of bankers and venture capitalists, and we were meeting to discuss the potential acquisition, development, and financing of a multimillion-dollar property.

On the day of this particular meeting, I had spent the morning at a muddy construction site meeting with contractors and inspectors. I felt comfortable leaving the construction site and walking into a board meeting wearing flannel when almost everyone else was wearing a suit and tie because I already had a very good working relationship with everyone there. I had confidence in myself, but more importantly, everyone in that room also had confidence in me. They respected me, and they knew I was not disrespecting them by dressing down.

So, the simple answer to the question of whether you can wear flannel in a boardroom is: Yes. However, what you wear and why you are wearing it can have an effect on the outcome of your meeting.

 

When ‘How You Dress’ Really Does Matter

A few months prior, I had attended a luncheon where one of the venture capitalists spoke to an audience of entrepreneurs. During his presentation, he stated unequivocally that if someone met with him to ask for an investment in his business and he was wearing jeans, the VC would absolutely not even consider investing in him or his company.

Contrary to what many young entrepreneurs have been taught through popular media, unless you are directly involved in a small minority of high-tech businesses and Mark Zuckerberg was your college roommate — or unless you already have a proven track record with the audience in question — dress really does matter.

 

What to Consider When ‘Dressing Down’

Even though we’ve become more laid-back as a society, that doesn’t mean you’ll be able to earn the respect of your peers and subordinates by “dressing down.” There are times when it’s okay to wear jeans and a flannel shirt, but there are some things you should consider first:

 

  1. Your audience.

    Attorneys, CPAs, bankers, investors, insurance agents, and government officials work in fields where a suit and tie (or at least a polo and khakis) is the norm. They may not admit it, but they will evaluate you based on your appearance. If anyone tells you differently, they’re either lying or delusional.

  2. Your track record.

    Once you’ve earned the respect of the people you work with, the people you work for, and the professionals who help your business succeed, your personal attire will have a less dramatic effect on how people view you. Once they are evaluating you and respect you based on your performance, dress becomes a non-issue.

    At this point, you can comfortably and confidently walk into a board meeting wearing a flannel shirt, pitch a multimillion-dollar project to a room full of investors and bankers, and walk out with a deal. But if you don’t have rapport with your audience and you insult them with your appearance, you will probably never be given an opportunity with them again!

  3. Your image.

    Many young entrepreneurs will immediately institute a casual dress code in their business. Why not? It’s more comfortable, and people like it. But I would caution you that it’s possible to be too casual.

    No matter what industry you work in, if you wear your pajamas and slippers to work, people are going to think you are lazy and a fool. Your peers won’t respect you (even if they are wearing something similar), your subordinates won’t respect you, and unless you’re Hugh Hefner, your customers probably won’t respect you, either.

If you do have a casual dress code at your company, encourage your managers to dress a little bit nicer than their subordinates. It will help them be treated with more respect and be taken seriously. Can you imagine being reprimanded by someone wearing pajama bottoms? Would you take him seriously? Neither would I, and neither would investors.

If you’re waving a dismissive hand and insisting your company is exempt because you run a “cool, fun tech startup,” consider this: I’ve seen pictures of Mark Zuckerberg in a jacket and a tie. At times, even he dresses for the occasion.

Yes, you can wear flannel into a boardroom, but should you? Always consider your audience, and consider how you want to be perceived. After all, you’re not a rebel — you’re a businessperson, and forming a poor impression by dressing down can be detrimental to your business and devalue you in the eyes of your peers. Over time, you can earn the right to dress however you want, but it takes a proven track record of success for your appearance not to matter.

 

Darrell Henley is a serial entrepreneur with over 20 years’ worth of experience in starting and growing businesses in a variety of industries, such as Internet marketing and travel. Darrell is passionate about every company he decides to invest in, and he works closely with his various business partners to develop each company’s highest potential.

 

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