The Five Best Dressed Women CEOs

April 19, 2024

The number of females in C-suite positions is on the rise. In fact, the percentage of women CEOs doubled over the last couple of years. In addition to power and confidence, these women have no shortage of style.

As women’s virtual stylists for executives and CEOs, we know how important it is to channel your personal brand. Not only through your work but through your appearance. 

Like it or not, first impressions are everything.

Looking for inspiration on how to dress like a CEO?

We’ve picked out five of the best-dressed women CEOs who use their wardrobe to project their ambitions and business-savvy. Read on to discover how they’re changing the conversation with style.

1. Jessica Alba’s Timeless CEO Fashion 

Though Jessica Alba got her start on the big screen, she’s made a name for herself in the business world. Her clean, sustainability-minded project The Honest Company, launched in 2012, is now a multi-million dollar, award-winning empire. 

Though she recently took a step back from the company, she continues to show her followers what CEO attire can look like. How? Through timeless, core-color-led outfits.

In the photo above, she keeps her ensemble professional with a black sweater, black pants, and a grey textured blazer. 

But, this look isn’t boring.

Many people hear neutral colors and think, “That’s not for me, there’s no variety. Sounds pretty old-school.”

So how does Alba avoid that? By infusing her attire with subtle, personal details. 

The gently oversized fit along with her makeup and accessories add a modern, feminine touch.

Note how she incorporates touches of her personal style through her colorful lips, earrings, and the fit of her jacket. 

These neutral colors never go out of style and make for easy mix-and-matching, while dressing up or down. 

That’s why we always recommend clients have core colors in their closets. Black, grey, navy blue, and white all go with each other. And, they go with bold colors and prints as well.

2. How to Dress Like a CEO in Spring: Angela Ahrendts’ Take 

From CEO of Burberry to the Senior VP of retail at Apple, Angela Ahrendts knows how to help big brands succeed.

She took her marketing and retail savvy from her time at heritage brand Burberry and infused it with Apple’s innovative spirit. These days she continues to advise and inspire young entrepreneurs (especially women) to carve their own paths.

The same goes for her CEO fashion.

A lot of online advice on how to dress as a CEO focuses on wearing dark, moody colors. After all, think of your traditional CEO and you probably picture a black business suit.

While most people in urban areas opt for dark colors, that doesn’t mean lighter hues are unprofessional.

In fact, they can set you apart from the crowd. And, make it easier to transition your closet from winter to spring

Above, Angela (second from the left) looks effortlessly chic in a crisp white suit jacket over a textured taupe dress. 

The dress is obviously a little sparkly for a normal nine-to-five. But, you could wear this look to a special event or gala.

Another option is to find a similarly light-toned dress in a material like cotton to wear to the office. 

Wear this, and you’ll instantly command attention in a room full of somber shades.

3. Lilly Singh’s Superwoman CEO Looks

Want to find CEO looks that shine? Look no further than Youtuber turned businesswoman, Lilly Singh

Singh has come a long way from her days of five-minute comedy videos under the name “SuperWoman”. She’s enjoyed success in acting and hosting while also creating her own production company, Unicorn Island. With every project, she brings her signature infectious energy, positivity, and sass.

So it should come as no surprise that she brings that same energetic twist to her wardrobe.

She loves bright pops of colors, unique patterns, and melding Eastern and Western fashion together.

If you’re struggling with how to combine CEO attire with your vibrant personality, look to Lilly for inspiration. Pops of color are ideal for fellow women CEOs or leaders who have an equally bold personal brand.

Wondering how to use color with intention?

In our proprietary Next Level Wardrobe Style System, step one focuses on color. A wardrobe that’s stuffed with too much color reads as disorganized and overwhelming. A monotone closet in all black or dark colors lacks versatility and leads to outfit fatigue.

That’s why the right ratio of core (black, white, navy, gray) to tonal (shades of core colors) to bolder colors is key.

As long as you wear colors intentionally, there’s no shade of the rainbow you can’t wear. (That’s right, stop listening to what the internet “color analysts” are saying.)

4. CEO Outfits for All: Katie Sturino’s Monochrome Mastery

Megababe CEO Katie Sturino is not only the founder of an innovative beauty brand focused on self-care rather than perfection. She is also an advocate for size inclusivity, empowerment, and a fashion icon.

Along with acting plus-size CEO styling, Sturino is also a master of the monochrome.

Take a peek at how she takes the “one and done” outfit formal to her outfit. What is this formula about? It’s when you pick one color and wear it from head to toe.

When wearing a monochromatic look, stay fresh by mixing up tones and fabrications. Notice how Sturino partners a silky slip skirt with a soft knit blazer.

With these expertly coordinated tonal shades, she’s created a multi-purpose outfit perfect for CEO fashion. Picture wearing this to give a conference talk, or an interview, then enjoying a night in the city.

5. Kyle Leahy’s Powerful CEO Attire

Knowing how to dress like a CEO is knowing how to employ Powersuiting.

If you’re not familiar with the concept, take a look at new Glossier CEO Kyle Leahy’s plum suit ensemble above. 

The same way that she’s breathed new life into the beauty brand’s image, she’s put a fresh twist on the power suit. 

Her suit is tailor-made for her. It has the classic look of a suit, but with contemporary nods like the color, wide-leg, and elongated jacket.

Her women CEO outfit says powerful, stylish, and in control.

We suggest every woman have a power suit in their wardrobe. It’s that fool-proof combination you can throw on for important meetings, a keynote speech, or starting a new position.

At the same time, while this look is easy to pair together, it’s also easy to break apart. You can easily wear the separate pieces with other items in your closet. Picture those trousers with a grey turtleneck and heels. Or the blazer over slim-fitting cream pants.

Are you inspired to dress like a CEO?

Feeling inspired by the style smarts of these best-dressed women CEOs? Check out our virtual styling services to work with an expert to elevate your wardrobe.

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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