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Home » Is It a Good Career Move to Dress Like Your Boss?
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Is It a Good Career Move to Dress Like Your Boss?

EditorBy EditorFebruary 3, 2026No Comments3 Mins Read
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Disney’s new CEO is sending a wink with his wardrobe, whether he means to or not.

Josh D’Amaro, who takes the helm of the Mouse House next month, has drawn attention for dressing much like his soon-to-be predecessor, Bob Iger. Both men regularly don sweaters over collared shirts and have a penchant for jackets paired with white dress shirts. At a celebration for Disney’s 70th Anniversary last year, the pair sported button-downs and dark slacks.

Bob Iger and Josh D'Amaro

Josh D’Amaro, second from left, and Bob Iger, holding the top of the bell.

Handout/Getty Images



While D’Amaro may just have a natural affinity for the same kind of attire that Iger sports, leadership experts say the similar look projects continuity to Disney’s stakeholders. The familiarity may resonate at Disney, where Iger has led the company on and off for nearly two decades — though it raises a question of whether the rest of us should dress like the leaders we hope to one day succeed.

“You want to avoid looking like a carbon copy of the person,” said Bradley Akubuiro, a partner at leadership advisory firm Bully Pulpit International in Chicago. “But there are elements that you want to keep if you can.”

Bob Iger and Josh D'Amaro

From left to right: Disney chairperson James P. Gorman; incoming CEO Josh D’Amaro; incoming president and chief creative officer Dana Walden; and CEO Bob Iger.

The Walt Disney Company/via REUTERS



Those elements should be modest, akin to how Apple CEO Tim Cook doesn’t deviate too far from the black turtleneck and jeans his predecessor Steve Jobs regularly wore, suggested Jennifer Eggers, president of executive advisory firm LeaderShift Insights in Pennsylvania.

A few years ago, she said a client of hers from a Fortune 200 retailer went overboard by wearing the same distinctive jewelry as his boss. When she met with his peers for feedback on his performance, several described him as a copycat.

“It really hurt him,” said Eggers. “We coached him, and he eventually lost his jewelry.”

Bob Iger and Josh D'Amaro

Iger and D’Amaro sport sunglasses and collared shirts.

Brendan McDermid/File Photo/REUTERS; David Paul Morris/Bloomberg via Getty Images



Still, there can be benefits to mimicking a higher-up’s sense of fashion when done subtly, added Akubuiro. “People have a tendency to like people who are more like them,” he said.

Just keep in mind the fuzzy warm feeling may be temporary.

“It’s effective as a bridge maybe, but not as a destination,” said Eggers. “Eventually, leadership credibility has to stand on its own.”

D’Amaro, who started at Disney in 1998 as a Disneyland business planner, faces a challenging road ahead no matter what he wears. He’s tasked with growing streaming platforms like Disney+ and Hulu to offset declines in its TV networks business, while easing ESPN’s transition into the streaming age.

While D’Amaro’s fashion style is similar to Iger’s, Akubuiro said the business-casual look has also made sense for his role as a park executive.

“This is kind of the uniform of someone walking around the parks, and so it gives him a very accessible feel,” Akubuiro said. “When you’re making a change, that accessibility is something that actually brings people in and gives them some confidence.”



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