The World’s 10 Most Fashionable CEOs

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Running a successful company no doubt comes with a lot of responsibilities. As the one in charge, a CEO oversees everything from employees to operations, all the way down to the bottom line. Some are just born with the personality archetype of a chief, but not all are also #blessed with a good fashion sense. 

Style is an innate character trait that has the capacity to be the top gun, but these two qualities also happen to be tap into different skill sets. The good news is, they’re not mutually exclusive. While some world-renowned CEOs throughout history have famously taken getting dressed out of their daily decisions by adopting a uniform—like Steve Jobs—others are actually celebrated for their fresh fashions.

We totally respect those who’d rather not exert brainpower on deciding what to wear if style doesn’t naturally run through their veins—they’ve got other things on their plate. But those few superhumans who can sit at the top in the coolest kits deserve a moment of appreciation. 

In no particular order, here are ten of the most stylish CEOs in the world today. Emulate both their work ethic and their fits.

1. Teddy Santis from Aimé Leon Dore

It’s no surprise that the man who outfits all the cool downtown New York City kids has a killer personal aesthetic. He’s a press-shy head guy who leads by example. ​​​​​​

2. Carol Lim from Opening Ceremony

When you’ve co-founded one of New York’s most iconic boutiques (Opening Ceremony), been half of Kenzo’s design duo for the better part of this decade and can call Chloë Sevigny a BFF, your cred eclipses everyone else's.

3. Heron Preston from Heron Preston

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You don’t become a venerated streetwear design icon if you don’t embody that image. Cue Heron Preston.

4. Neil Blumenthal and Dave Gilboa from Warby Parker

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Gentlemen, we have a twofer. Blumenthal and Gilboa are two business dudes who can also throw some pretty sweet thread combos together. Their style is casual but elevated, classic but cool—specs included.

5. Gwyneth Paltrow from Goop

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Gotham/GC Images

Paltrow might have an unfair advantage, but we would be remiss not to give her impeccable style a nod. She’s always had that fashionable je ne sais quoi, and now she’s a boss, so here we are.

6. Jerry Lorenzo from Fear of God

Lorenzo lives and breathes his streetwear label, Fear of God, and that intensity manifests in his style sensibility. Running the show while personifying the brand’s aesthetic is literally his way of being.

7. Ben Gorham from Byredo

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Matthew Sperzel/GC Images

It makes sense that a dude with a supernatural olfactory sense would also school us all on personal aesthetic. Just like his fragrances, Gorham’s style is bold, sophisticated and cool AF.

8. Emily Weiss from Glossier

She disrupted the already very saturated beauty industry, and brands would never be the same again. So, yeah, she dresses the part.

9. Tomoaki Nagao (aka Nigo) from A Bathing Ape

A seasoned creative with a music career under his belt, Nagao is also the mastermind behind the streetwear label A Bathing Ape. The crowd he runs with (Virgil, Tyler, Rocky) says it all.

10. Ronnie Fieg from KITH

He founded one of the world’s most recognized and celebrated streetwear brands. His vibe is a thing of legend at this point.

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