The CEOs of the country’s top companies certainly have the means to dress as well as they want, but money doesn’t necessarily translate to fashion. While looking the part of a leader is one of a CEO’s priorities, the finer points of fashion are often lost on someone leading a Fortune 500 company. Yet if a CEO has a personal style, it can send a positive message. And it’s not a matter of shelling out for the priciest designer goods. An executive’s suit may have cost $6,000, but if it’s not tailored for the best fit, it’s not going to look sharp.
Despite the prevalence of the Silicon Valley aggressively casual CEO look, in the ranks of the Fortune 500 the suit still matters — for both male and female CEOs. And within this group, a few business leaders stand out with a certain “look.”
1. Larry Ellison
The departing CEO of Oracle Corporation (ORCL) and Silicon Valley icon has a habit of pairing black mock turtlenecks with tweed jackets for public appearances, evoking college professor-meets-tech mogul. For casual situations he’ll switch out the turtleneck for a black V-neck, creating an overall effect that’s consistent and a bit youthful for his 70 years. It’s worth noting that Larry’s son David recently launched a men’s clothing line inspired by his father’s Hawaiian island of Lanai.
2. Bob Iger
The CEO of The Walt Disney Company (DIS) favors wearing a check pattern with his suits, whether it’s a gingham or large-check print, on a shirt or on a tie. And although checkered shirts have become common in business wear, no one does it better and with a more polished appearance than Iger. He’s also not opposed to a stripe or dot pattern for his ties, but he sticks to blue as the accent color.
3. Ralph Lauren
As the founder of the eponymous Ralph Lauren Corporation (RL) clothing company, Ralph Lauren is a literal rags-to-riches story who began his fashion line by turning rags into ties. He embodies his company’s fatigues-as fashion and aged-leather casual style. When the man dresses up, the fit is impeccable and he doesn’t shy from a stripes and plaid power clash. In the case of this CEO, dressing well is his job, and he does it with panache.
4. Marissa Mayer
While Yahoo! Inc. (YHOO) edged out of the Fortune 500 this year (ranked 522), this list would be remiss without including Marissa Mayer, who is one of the only CEOs you could pick out of a lineup just by her trademark silhouette: form-fitting jacket, mid-length A-line skirt falling just above the knee. Mayer understands that fashion is an art form, and while her pieces tend to stick to her favored shapes, she lives in vibrant colors. She is on record as favoring Oscar de la Renta and great shoes, and takes a front-row seat at Fashion Week.
5. Jack Dorsey
Twitter (TWTR) may not be in the Fortune 500, but one of its founders, Jack Dorsey, is representing Silicon Valley in a contemporary and more stylish manner than we have become accustomed. When he’s in one of his trim-cut suits, you don’t notice that he’s often not wearing a tie, and he often wears a reverse collar shirt by Dior Homme. However, Dorsey didn’t always wear designer fashion–as a younger man he sported spiky blue punk hair.
6. Jamie Dimon
When he’s wearing a suit, the CEO of JPMorgan Chase (JPM) shows that sometimes it’s about not drawing attention. His American-cut suits fit perfectly, but you may not notice unless you’re looking. However, Dimon’s casual style, which tends toward the Hawaiian shirt, is another matter.
7. Fabrizio Freda
Impeccably dressed in double-breasted suits, the Italian-born CEO of the Estée Lauder Companies Inc. (EL) looks like a man in charge, and his highest quality shoes set off his classy image. You won’t catch Freda photographed in denim–his closest to casual style appears to be a single-breasted suit.
8. Indra Nooyi
The Indian-born CEO of Pepsi (PEP) tends to wear black accented with jewel tones, often with a colorful scarf nodding to her heritage. Nooyi sometimes appears at social events in a sari, and she told the Economic Times that wearing traditional dress wasn’t always a choice: when she was first starting out, she couldn’t afford a business suit. “What I would not do is flaunt my Indianess by wearing a saree to work everyday, because it distracts from the job.”
9. Howard Schultz
The Starbucks (SBUX) CEO’s suits allow him to cut a slim silhouette, and while he’s typically not photographed without a tie, he manages to look put together yet casual.
10. Kevin Plank
The CEO of Under Armour (UA) is often photographed wearing his company’s own sweat-wicking performance apparel as casual and action wear. More unconventionally, he’s not opposed to wearing it under a suit jacket, either.
Colleen Kane is a New York-based freelance writer.