Here are 10 of the best dressed CEOs in the U.S.

December 18, 2014, 11:00 AM UTC
Designer Ralph Lauren acknowledges the crowd following the Fall/Winter 2012 collection during New York
Photograph by Carlo Allegri — Reuters

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

HOLLYWOOD, CA - MAY 14: Larry Ellison and Nikita Kahn attend the premiere of "Star Trek Into Darkness" at Dolby Theatre on May 14, 2013 in Hollywood, California. (Photo by Jason LaVeris/FilmMagic)

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

NEW YORK, NY - MARCH 20: Bob Iger attends the "Aladdin" On Broadway Opening Night at New Amsterdam Theatre on March 20, 2014 in New York City. (Photo by Walter McBride/WireImage)

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

Designer Ralph Lauren acknowledges the crowd following the Fall/Winter 2012 collection during New York Fashion Week, February 16, 2012. REUTERS/Carlo Allegri (UNITED STATES - Tags: FASHION PROFILE) - RTR2XZL9

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

In this photo provided by the Palazzo Chigi press office, Italian Prime Minister Matteo Renzi talks with Yahoo CEO Marissa Mayer, during a visit to their headquarters in San Francisco, Ca, Monday, Sept. 22, 2014. (AP Photo/Palazzo Chigi press office, HO)

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

Kate Greer, Jack Dorsey== TIME 100 Gala, TIME's 100 Most Influential People in the World== Jazz at Lincoln Center, NYC.== April 29, 2014== Photo - Patrick McMullan/ == ( via AP Images)

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

DETROIT, MI - MAY 21: JP Morgan Chase CEO Jamie Dimon, center, attends a luncheon May 21, 2014 in Detroit, Michigan. Dimon announced during the luncheon that JP Morgan Chase will invest $100-million to help the city of Detroit with blight removal, urban development, home loans and retraining people in the work force. (Photo by Joshua Lott/Getty Images)

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

NEW YORK, NY - JUNE 16: Mary-Ann Freda (L) and CEO of The EstÈe Lauder Companies Fabrizio Freda attend the 2014 Fragrance Foundation Awards on June 16, 2014 in New York City. (Photo by Bryan Bedder/Getty Images for Fragrance Foundation)

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

Indra Nooyi, chief executive officer of PepsiCo Inc., center, is surrounded by delegates and members of the media as she walks through at the Myanmar International Convention Center during the World Economic Forum on East Asia in Naypyidaw, Myanmar, on Thursday, June 6, 2013. Unilever and Coca Cola Co. are among attendees at the three-day World Economic Forum on East Asia hosted by Myanmar this week. Photographer: Dario Pignatelli/Bloomberg via Getty Images

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

CEO of Starbucks Howard Schultz (C) smiles after inaugurating the coffee chain's first Colombian store at 93 park in Bogota July 16, 2014. REUTERS/John Vizcaino (COLOMBIA - Tags: BUSINESS) - RTR3YXQL

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

NEW YORK, NY - JANUARY 31: Under Armour Founder and CEO Kevin Plank attends the closing bell at New York Stock Exchange on January 31, 2014 in New York City. (Photo by Joe Kohen/Getty Images)

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.

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