CEO Secrets: What's a modern boss to wear?

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Louise O'Shea Image source, Confused.com
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Louise O'Shea, CEO of Confused.com, is struck by gender differences in the new world of informal workwear

A new culture of working from home and video conferencing has ushered in a trend for informality in the workplace, including what we wear. CEOs set the tone for their companies. So can they now dress down a bit?

"Our post-pandemic lifestyle has taught me that I don't need to dress smartly for work every day," says Louise O'Shea, CEO of insurance comparison site Confused.com, "especially when we've all seen each other's realities when working from home.

"But I do it because I enjoy it," she adds. "And putting on some of my best workwear and doing my hair and makeup before each working day has become a sort of personal ritual for me, allowing me to go from one state of mind to another and putting my 'best self' forward."

Fiona Gordon of advertising agency Ogilvy UK agrees. "I think CEOs can definitely be more informal than they were," she says.

"The pandemic has moved the dress code for everyone. But for me personally, if I'm going to present to a big room, I like to feel the energy and I do get that from what I wear.

"For example, putting lipstick on is one of my personal triggers for confidence."

Fiona Gordon
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Fiona Gordon, CEO of Ogilvy UK, says bosses can be more informal with their clothing choices now
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These women are just two of the many CEOs now facing a wardrobe dilemma. How do you present yourself to be taken seriously for business in a world that seems much more open to informality? Are those in charge ready to change their wardrobes, in line with their workforce?

Peter Done, CEO of Manchester-based HR specialists Peninsula, isn't ready to mothball his suit just yet.

"I wear a suit to the office every day," he says. "This conveys a certain standard that I have set for myself, both personally and professionally. As CEO, it's up to me to lead by example. If I expect employees to dress smartly then I should do the same."

While acknowledging that the pandemic has changed expectations, allowing employees to dress in a more casual style that used to be associated with the tech sector, Done believes that dressing professionally puts you in a better frame of mind for work.

"I believe it is good business practice to dress smartly," he adds. "It all comes back to customer service, leaving people with a good impression, showing that you care and want them to come back.

"If someone were to turn up to a meeting in ripped jeans or flip flops - unless it were out of hours and very last minute - to me that shows you don't care. First impressions count and you only get one chance to make a good one."

Peter Done Image source, Peninsula
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Peter Done, CEO of Peninsula, says it is important to make a good first impression with your attire
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The pandemic has accelerated the level of informality that companies accept, according to Ben Whitter, head of employee coaching and consultancy firm HEX Organization.

CEOs want to appear to be more human and not just some corporate robot in a suit, he says. "Someone that people feel comfortable around, is relatable, and we can have confidence in."

He also argues that (at least for men) the suit and tie combination was becoming a tainted brand well before the pandemic, thanks to a whole series of high-profile stories like the MPs' expenses scandal, the Enron collapse, and the 2007-08 banking crisis.

"It's no longer taken for granted that the suit is the uniform of a trustworthy person," he says.

But Peter Done refutes this. "Suits don't make any difference, it's the credibility of the individual that counts," he counters.

So what should a leader who wants to be seen as relatable and authentic wear?

Dragons' Den Image source, Andrew Farrington
Image caption,
Steven Bartlett (second from right) became the youngest ever Dragon on Dragons' Den at the age of 28. He does not wear a suit on the show

The latest recruit to the TV show Dragons' Den, Steven Bartlett, vowed when he became a panellist that he would never wear a suit.

He says he wants to represent a new breed of young business leader that is true to himself and doesn't stand on ceremony.

The CEO's role, and the expectations placed on them, can vary a lot depending on the size of the company. This too might affect their choice of clothing.

Bosses of smaller start-ups don't usually feel the need to stand out from their team, but they do need to impress and quickly build trust with potential new clients and investors.

Joel Remy-Parkes has turned a successful side hustle selling kids' tableware into a growing small business.

He works out of a large co-working space where you will struggle to find anyone wearing a suit and tie.

"The lockdown almost stripped everyone down to their comfort essentials and we all began to discover a new level of appropriate dress code," he says.

It's a development he welcomes, but it poses a dilemma when he is getting ready to meet new people.

"If I had to meet an investor or potential partner, I would honestly feel a little odd rocking up in my Wu-Tang T-shirt. But on the flip side, I would be absolutely delighted if she was wearing one too!"

Joel Remy-Parkes Image source, Joel Remy-Parkes
Image caption,
Joel Remy-Parkes prefers T-shirts to suits for business meetings
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The move to informal dressing at the top may sound liberating, but is it an equal one across the gender divide?

Some argue that it is easer for male CEOs to adopt this new informal style.

"The pressures for women are extremely high," says Confused.com's Louise O'Shea.

"Quite often when I do broadcast interviews, comments are made about my appearance, particularly my hair. While this might not seem like anything major, it's led me to have conversations with my male counterparts on whether this would ever happen to them.

"Guess what? It hasn't."

She adds: "I do often wonder what the reaction would be if I appeared live on TV without brushing my hair or doing my makeup. Would I be known as the CEO who never made an effort, or the CEO who was ready to challenge old expectations?"

But not everyone agrees that the odds are stacked against women in this regard.

Fiona Gordon of Ogilvy UK thinks this shift to casual could present some unexpected positives for women. "Women, you could argue, will have more opportunities than men because women traditionally can wear more diverse clothes so can be more expressive of themselves, whereas for men there is a kind of uniform in a way.

"It is quite good to be memorable. People's attention is satiated with so many images," she adds.

Mark Zuckerberg Image source, Justin Sullivan
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Mark Zuckerberg, pictured here in 2010, made his name as the hoodie-wearing boss of Facebook

Sara Simmonds, a former fashion entrepreneur who now coaches CEOs across different sectors, believes women and men are judged equally in terms of style and appearance.

"We only want to do business with those we trust, and that first impression comes from what you wear and how you present yourself, no matter your gender," she says.

Whether you choose to dress formally or casually, you still need to pay close attention to what you wear, she says.

"Informal dressing can set your clients at ease, but first impressions still count. Jeans that fit well, trainers that are clean, and T-shirts that are crisp are essential. And you should add something to this that is your signature touch, you need to have a style and stick with it.

"Your clothes are a silent sales weapon."

You can follow CEO Secrets producer Dougal Shaw on Twitter: @dougalshawbbc

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