How To Dress Like A CEO: Men’s Guide

February 2, 2024
4 Questions to ask yourself when getting dressed for work for him

Some guys like a relaxed dress code and not thinking twice about what they wear. But if you’re an executive, CEO, or entrepreneur, you know the importance of appearance. 

How you dress and present yourself to others can help you level up or hold you back in your career. Many successful men know that, and that’s why they turn to an Executive Image Consultant to help them out.

At Next Level Wardrobe, we’ve helped hundreds of guys figure out what to wear to work, no matter their industry. 

Today, we’re peeling back the curtain and sharing some of those exclusive tips with you. Keep reading to learn how to dress like an executive man, outfit tips, and style role models to inspire your wardrobe.

How To Dress Like an Executive Man

A lot of men want to know how to dress like an executive. They want that quick, Google-able answer that tells them the one fail-proof outfit they can wear every day.

In reality, there are so many dress codes and insider rules that change depending on your industry. What works for your stock broker friend won’t work for your buddy who’s starting his own business, or your pal in Silicon Valley. 

So when we meet with clients, instead of forcing everyone into a suit, we ask them these four questions: 

1. What Is the Industry That You Work In?

Applying to be a VP at a bank may mean wearing a traditional suit and dress shoes. But applying to be a VP at a tech company could mean sneakers and a cardigan. Knowing how to look like an executive means understanding the industry culture you’re in and dressing accordingly.

2. Is There a Dress Code?

We’ve surveyed our Instagram followers before and found that about 50% of people have no clue what their dress code is. 

If you don’t know what your dress code is, talk to HR. It’s their job to be able to tell employees what to wear and what to avoid.  Ask them as many questions as it takes to get a clear answer. That way, you’re not taking wild guesses.

3. What Is on Your Calendar?

Style should be personalized to you and your lifestyle. Your outfits should work with your day, not make things harder. That’s why you should think about your day-to-day, what you have coming up, and what that means for your wardrobe.

For example, we had a client who was a CEO in the Tech industry. His job meant traveling constantly, so he needed low-maintenance clothes. The items we chose for him still needed to look polished, but also easy to pack, non-iron, and activity-friendly.

4. What Is Your Personal Brand?

Finally, if you want to dress like a CEO, you need to know your personal brand

Your personal brand is who you are and who you want others to perceive you to be. It comes from a combination of how you dress, talk, walk, act, and even smell. It’s the overall vision of who you are.

A CEO is their own business card, so they have to be very intentional with the first impressions they create. (Especially because it only takes seven seconds to form life-long assumptions about someone.) 

Figure out your brand, and you’ll unlock CEO style for yourself. 

What Is the Best Outfit for a CEO?

There is no one “best” outfit for a CEO. It all depends on how you answered the four questions above. That’ll determine what to look for in the best outfit for a CEO, and in your wardrobe overall.

Once you do answer those questions using outfit formulas is a great way to simplify and systemize getting dressed each morning. 

No matter your personal brand or style, you can follow these three outfit formulas: 

  1. The Core Color Formula: Mix and match any core color together. Core colors are black, white, grey, and navy blue.
  2. The 1-2-3 Formula: Wear a top in one core color, a bottom in another, and a layering piece in an accent color or pattern or a core color.
  3. The One and Done Formula: Pick one color and wear it from head to toe.

How To Look Like a CEO: 3 Examples From Image Expert, Cassandra Sethi

We’ve given you the building blocks to start creating your own executive closet. But since style is so visual, we want to give you three examples of how to look like a CEO. 

We asked NLW founder Cassandra Sethi who she thinks men should look up to for CEO style. Here are her three top picks:

1. Mark Cuban: Men’s Formal Wear

Sharks, our first CEO style role model is none other than Mark Cuban.

As a TV personality, investor, and philanthropist, Mark knows how important style is to a professional brand. Whether he’s at a speaking event or on TV, he always looks sharp, and clean-cut, yet never stuffy.

If you work in a more formal office environment like finance or law, you should look to Cuban’s style as inspiration.

Let’s break down why his outfit works.

First, he’s wearing core colors. We’ve mentioned them before, but black, navy blue, grey, and white are those “core” neutral colors that go with everything. You can use them as the foundation for any outfit.

These colors help Mark look polished and put together.

Second, the tailoring and fabrics are on point. Fit is hard to point out because if something fits well, you don’t notice it. But everyone can see a poorly fitting suit. 

At the level Mark Cuban is at, everything should fit like a glove. Small details like the design of his lapels and the sleek fabric of his jacket make a big difference.

Third, Mark uses subtle accessories to enhance his look. That’s right, guys can have fun with accessories too, it doesn’t have to be boring!

The green pocket square tucked into his breast pocket shows a dash of personality. You can also spot an Apple watch on his wrist, which shows that he’s tech-minded and approachable.

2. David Beckham: Casual Business Attire

As a pro-soccer star turned business mogul, you can imagine that David Beckham has a very different brand than Mark Cuban. But he proves that even when you work outside of “traditional” or “conventional” work environments, you can still look stylish.

The secret David follows is keeping things uncomplicated. Great style is simple, but you need to have the right pieces in your closet and a sustainable strategy.

His power casual outfit works so well because it centers on basics. He’s wearing a great pair of trousers and a well-fitting sweater. He’s not reinventing the wheel, he’s just picking well-made, well-fitting pieces that’ll look good for years to come

3. Shamier Anderson: Executive Casual

Actor and producer Shamier Anderson is a co-founder of Canada’s largest venture fund for BIPOC founders. It’s a unique mix of a job, and he keeps his style equally distinct.

Above, he looks powerful, cool, and confident in a pair of black trousers, loafers, and a printed polo.

This menswear look works well for a couple of reasons.

One of my favorite elements is Shamier’s double monk loafers.

They take his style to the next level. They show how you can add extra detail and consideration to your look without going overboard. 

You’ll also notice how the modern pattern on Shamier’s polo keeps his outfit feeling fresh. Instead of going for a typical solid-colored polo that might read as too old-school or stuffy, he added his own twist.

But again, he doesn’t go too “out there” with his pattern choice by grounding it in neutral colors.

Everything about his look feels intentional without trying too hard. That’s the key to acing executive casual style. By being intentional with your choices, you can have a wardrobe that makes feeling powerful and confident easy.

Ready to dress like a CEO? Create and enhance your executive brand by applying for our men’s image consulting services today.

About the Author - Cassandra Sethi
About the Author - Cassandra Sethi

Personal Stylist & Image Consultant

Cassandra Sethi is a Personal Stylist and Founder of Next Level Wardrobe, a luxury Personal Styling and Shopping Service that helps successful professionals of all ages and sizes. After working in the fashion industry for over 25 years, she used her expert knowledge to create a proprietary styling system called ‘The Next Level Wardrobe Style System' which guarantees clients more outfits with less items in their closet. NLW has been featured in The Wall Street Journal, The Tamron Hall Show, NY Mag, Huffington Post and more.

*Disclosure: Next Level Wardrobe only recommends products that we’d suggest to our clients or personally wear ourselves. All opinions expressed here are our own. This post may contain affiliate links that at no additional cost to you, Next Level Wardrobe may earn a small commission. Read the full privacy policy here.

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Cassandra Sethi

is a NYC Personal Stylist and Image Consultant. She is the Founder of Next Level Wardrobe and 'The NLW Style System' that guarantees clients more outfits with less items.

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