How to Dress Like a Leader

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So you have made it as a leader in your field. Congratulations!

Does your look portray the success, prestige, and power behind your position?

Does it command respect from your peers and those looking up to you in their careers?

You don’t have to be CEO to have “CEO style,” you just have to want to use your wardrobe to expand your influence and to create a memorable impression.

In my work with corporate clients, I help men develop their personal brand and then align their wardrobe choices to that brand for maximum impact in the workplace. Here’s how men in leadership positions can dress like a CEO.

What do well-dressed CEO's images have in common?

As a corporate leader, you often find yourself as the focal point or center of attention due to your position, so your style should whisper, not scream, your personal branding message. You can convey confidence in a way that isn’t loud and obnoxious.

Their wardrobes support their story: their personal road to success,  their values, leadership style and more. Whatever message they are delivering, they use their style choices to enhance, not distract from that concept. 

Dressing like a male CEO means keeping it simple. 

Focus on fit over trend, core colors over flashiness, and high-quality pieces over quick fixes. This will ensure you look not just professional, but like a competent leader, all the time.

Three CEO Style Breakdowns

#1: Tim Cook, CEO of Apple
Tim Cook's CEO style

In 2009, Tim Cook defined the future of Apple in declaring, “We believe that we are on the face of the earth to make great products and that’s not changing.”

Cook’s wardrobe communicates that through his simple yet powerful use of core colors to demonstrate capability, and also to stand out.

The pops of white in an otherwise dark outfit command attention, and he communicates that both he and his brand are trustworthy and intentional (which makes me want to buy the newest iPhone out there, right?!).

His black and white sneakers bring an approachability to his vibe, inviting us to trust what he stands for.

#2: Jeff Bezos, Founder of Amazon
Jeff Bezos CEO style

Bezos’ transformation between these two photos demonstrates the potential your wardrobe really has when it comes to communicating power and being seen as a power player.

He moves from a sloppily-dressed, nerdy dad vibe to a competent, traditional, and polished look.

The lesson we can learn from Bezos about CEO style is fit.

Many male executives I’ve worked with hear “fitted” and think “hot, uncomfortable, and tight.” But this is simply untrue.

A well-fitted outfit will make you more comfortable, not less, especially if you were wearing baggier clothes before. In fact, most of my male clients are always so surprised how easy it is (with an expert’s help) to create a style that is stylish and comfortable.

#3: Tyler Perry, Actor and Founder of Tyler Perry Studios
Tyler Perry's CEO style

Some male CEOs and business leaders have a sense of style and they understand their brand can be conveyed through their clothing, but they simply need an update.

Perry is a perfect example of someone who updated his image to change with the times, as his first khaki-colored suit and brown shoes communicated an old-fashioned vibe that wasn’t aligned with his cutting edge company mission.

Now, as he integrates core colors and textures, his fresh feel shows he has his life and business together. His suede jacket and scarf show he’s willing to take a risk, but doesn’t have to be the center of attention- he lets his expertise and skills speak for themselves.

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Picture of Cassandra Sethi

Cassandra Sethi is a NYC Personal Stylist and Image Consultant. After working over 15 years in the Fashion Industry, most recently as a Senior Buyer for Equinox, she created her business, Next Level Wardrobe – a luxury personal shopping service for successful professionals. Cassandra’s been featured in Greatist, Livestrong and NY Mag.


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