Dress like a CEO

Ready for a shortcut to your CEO style? Apply to work with Cassandra here!

When you progress in your career, people begin to notice elements of your fashion choices they wouldn’t have otherwise. 

CEO style means using image to your advantage to represent who you are and what you, and your brand, stand for. Are you communicating the right message with your fashion selections? 

I’ve worked with CEOs and high-level executives in my virtual styling sessions, where I discuss with clients the exact message they want to convey with their wardrobes, and help them turn that into a  powerful work wardrobe. 

Check out these inspiring founders and CEOs, running their own businesses and using their style to gain the upper hand in their workplaces with enviable (but doable) CEO style.

Sonia Cheng, CEO of Rosewood Hotels

Sonia Cheng, who graduated from Harvard and became the CEO of Rosewood Hotels at age 30, knows how to make a statement with classic pieces. 

Cheng pairs a simple white turtleneck with a fun black and white plaid blazer. She is using simple but classic core colors to build a capsule wardrobe that conveys clean lines and timeless style. 

You can copy her look by investing in basics in these core colors, then accentuating these outfits with your statement pieces and minimalist accessories.

Oprah Winfrey, Former Talk Show Host and founder of Harpo Productions

Oprah Winfrey’s outfits have evolved over the years, as the country watched the TV star has built her mega brand and businesses. 

She utilizes the wrap dress and v-neck style on dresses and blouses, which is a flattering choice for women with larger chests. 

Accessories, such as her bracelet and her iconic glasses, help her stand out as a CEO who isn’t afraid to make a bold statement, while keeping the rest of her outfit subtle. 

You can borrow this strategy by not being afraid to take risks in your fashion choices, as long as one accessory or item is the focus of the outfit and multiple aren’t competing for attention. Remember, CEO style is all about a whisper, not a scream. 

Julie Wainwright, Founder and CEO of the Real Real  

Founder of a luxury consignment company and movement, Julie Wainright has mastered the art of choosing a shoe that conveys confidence and power. 

This leather boot is perfect for any leader and can be paired with skirts and dresses to elevate your style and sense of self. Leather boots don’t have to have heels like Julie’s, but either way they can be a powerhouse shoe for many outfits. (They don’t have to be 5 inches tall either if you don’t like to wear heels!)

She also wears cashmere turtlenecks in a variety of core colors, which makes for easy mixing and matching with statement pieces, prints, and accessories. When you are CEO, you don’t have time to think about your style, it’s important that you create a long lasting system (or hire an expert) to ensure you look your best every day. 

Diane Von Furstenberg, Founder of DVF

Best known for inventing the wrap dress, this 73-year-old Belgian fashion designer proves that style has no age limit, and that conservative fashion for leaders doesn’t need to be boring. 

Take a note from Diane’s wardrobe by incorporating fun prints, like her leopard print skirt here. Being strategic about the prints that you wear and always pairing them back to core colors is the best way to make your style feel like YOU and make more of a statement. 

While you may feel pressure as a CEO to wear conservative styles and core colors only, this isn’t necessarily true all of the time; prints can communicate approachability and friendliness, traits that make your presence more memorable and support your story. 

To choose a print that works for you, simply pay attention to what you like and what grabs your attention when you are shopping- no need to overthink!

Emily Weiss, Founder of Glossier

Emily first became a public figure in 2007 when she was featured as an intern on MTV’s The Hills, but since then she’s catapulted to the front of most cosmetic companies as the founder beauty startup Glossier and blogger of Into the Gloss

In her feature for Vanity Fair she’s photographed in brown pants and a blazer by Bottega Veneta with a simple white tee underneath. This outfit aligns with her consistent style of “less is more,” and that fashion shouldn’t detract from your message, but rather let it shine through. This is consistent in her brand as well, which advertises “skin first, makeup second.” 
Here she is wearing a monochromatic outfit in white, which is one of the easiest and most effective CEO style strategies I use with my executive image styling clients.

More Posts Related to CEO Style

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.


For immediate help to upgrade your work style (virtually or in person), use this link to apply for a style consultation.

To receive my complimentary guide, 3 Items You Need In Your Closet Today, click here to put in your name and email.

Apply for a style consultation for immediate help to upgrade your style

Download my complimentary guide, 3 Items You Need In Your Closet Today

Next Level Wardrobe
[email protected]
Follow Me:
Newsletter Sign Up: