Tech execs and fashion -- an up-close look at the carefully cultivated personal styles of the Valley's elite

Jason Kempin/Getty Images for Rush Philanthropic Arts Foundation; Justin Sullivan/Getty Images; Jamie McCarthy/Getty Images; Kelly Sullivan/Getty Images for Sierra ClubFrom left: Bozoma Saint John, Satya Nadella, Arianna Huffington, and Jack Dorsey.

Silicon Valley is known for a lot of things, but high-fashion isn’t one of them.

Its elite show up to meetings in pajamas, fleece vests have become the go-to uniform of venture capital investors, and many high-powered executives are so obsessed with efficiency, they have adopted a boring, unfashionable uniform they wear each day without fail.

But don’t let the Valley’s nerdy reputation fool you – there are plenty of executives who dress to impress.

Instagram’s Kevin Systrom has proclaimed that he’s “probably the only guy in Silicon Valley who enjoys wearing a jacket or a tie,” while Snap CEO Evan Spiegel (who is actually based in LA) has appeared in the pages of Italian Vogue. Uber’s Bozoma Saint John doesn’t shy away from bright colours or daring designs, and Microsoft’s Satya Nadella is often spotted in $US500 designer sneakers.

Business Insider pored through photos of the top executives in the world of tech to determine who has a great fashion sense and who needs some help. We eliminated anyone who simply doesn’t care – Alphabet’s Sergey Brin – or those who always look presentable if a bit bland, like HPE’s Meg Whitman.Others, like Apple’s Jony Ive, made the list because of their role within the company they work for – Ive is design chief at Apple, so his fashion choices must face some scrutiny.

The ranking was based, whenever possible, on three clothing categories – casual, business, and formal wear – and were further evaluated for attention to trends, fit, and colour choices.

For each exec, we also found some of their exact clothes – or similar items – so you can replicate their look.

What follows is a non-scientific ranking of the fashion sense of some of the top executives in Silicon Valley:

19. Mark Zuckerberg, CEO of Facebook

Kimberly White/Getty Images for Breakthrough Prize

The Facebook’s CEO cleans up nicely at awards ceremonies (pictured above) and his clothes are always well-fitted. Another point in his favour: in recent years, he’s ditched his signature hoodie.

But he’s at the bottom of the list due to his insistence these days on wearing one thing and one thing only: A grey crewneck t-shirt, jeans, and Nike running shoes.

Get Zuckerberg’s look:

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Brunello Cucinelli cotton crew neck t-shirt, grey: $US295 (Zuckerberg wears the brand, but his tees are special made and reportedly cost between $US300 and $US400).

Nike Flyknit Lunar 3, wolf grey:$US150

18. Jony Ive, chief design officer at Apple


Apple’s design boss, Jony Ive, is regarded as one of the most respected minds in design. He’s responsible for the look and feel of every Apple product, including the packaging.

Ive can look good in formal wear; he has a quirky penchant for white tie ensembles and throwback looks, like coats with tails. And he gets points for creativity with his clothing choices. But overall, his personal packaging could use some refining.

His pants are often too long and his shirts too oversized. He often opts for garish colours like orange jackets and red socks. He also frequently looks rumpled and disheveled.

Get Ive’s look:

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Belstaff Gaynesford striped sweater, $US255

Clarks Wallabee boot in maple suede, $US140 (Ive has these chukka boots in at least two colours)

17. Reed Hastings, CEO of Netflix

David Becker/Getty Images

Hastings’ most frequent fashion faux pas is wearing one too many shirts. Note his prominently visible undershirt in the middle photo below. Not also, in the photo above, how he’s wearing a shirt, sweater, and jacket indoors.

But Hastings balances things out with his Netflix-themed holiday sweaters. He tends to wear them on quarterly earnings calls, making him one of the few tech CEOs with a great sense of humour.

Get Hastings’ look:

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Calvin Klein muted stripe polo, $US40

Common Projects original Achilles full-grain leather sneakers, $US430

16. Daniel Ek, CEO of Spotify

Andrew Burton/Getty Images

When it comes to personal style, Daniel Ek gets points for knowing what works for him.

The Spotify CEO has a go-to “look” that he more or less sticks to for most public appearances: jeans, sneakers like Nike Air Force 1s, and a graphic t-shirt, with or without a blazer.

While he’s not bringing anything very innovative to the table – in fact, that specific combination peaked in the mid-2000s – he dresses pretty much like you’d expect the head of a music streaming giant to dress.

Get Ek’s look:

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Think Out Loud Apparel acoustic guitar t-shirt, $US15.99 (Ek has this exact t-shirt! At least he’s a bargain shopper)

Nike Air Force 1 ’07, $US90

15. Tim Cook, CEO of Apple

Justin Edmonds/Getty Images

Tim Cook’s wardrobe consists mostly of jeans, t-shirts, blue shirts, and crewneck sweaters – plus the occasional tuxedo. It’s not super interesting, but it’s at least a bit more varied than that of his predecessor, Steve Jobs.

Cook’s biggest style shortcoming is that when he does put on a suit, it often doesn’t fit him correctly and he usually opts for something unimaginative, like black-on-black jacket and pants, as my colleague Dennis Green has noted.

Get Cook’s look:

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Bonobos slim fit denim sport shirt, $US128

Nike Roshe One, $US75

14. Sundar Pichai, CEO of Google

Justin Sullivan/Getty Images

Google CEO Sundar Pichai falls into a similar category as Cook: Serviceable, but not exciting.

What sets Pichai apart is his preference for track jackets and zip-up sweaters. He’s photographed wearing one at most public appearances – including several recent Google keynotes – and usually pairs them with jeans and pricey sneakers.

Pichai’s style choices tend to be more interesting that his contemporaries. And he’s typically more stylish than his boss, Alphabet CEO Larry Page.

Get Pichai’s look:

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The Kooples contrast yoke track jacket,$US425

Lanvin suede and patent leather low-top sneakers, $US495

13. Susan Wojcicki, CEO of YouTube

Steve Jennings/Getty Images for TechCrunch

As the CEO of YouTube, Susan Wojcicki has one of the coolest jobs at Google – and a wardrobe to match.

Wojcicki’s style is pretty straightforward – she tends to choose solid colours and simple styles – but she’s always perfectly dressed for each occasion.

Her cropped leather jacket and ankle boots at Google I/O helped her stand out as one of the few women on stage, and knee-high boots at the Fortune conference helped make an otherwise standard shift dress a bit more interesting.

Get Wojcicki’s look:

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Emerson Rose leather jacket, $US349

Nine West Argyle boots, $US119

12. Elon Musk, CEO of Tesla, SpaceX, and Neuralink

Justin Sullivan/Getty Images

Elon Musk is a billionaire, thrice-over CEO, serial dater of famous actresses, and the real-life inspiration for Tony Stark. Luckily for him, his style choices just about match that.

While his choices can occasionally veer into “dad” territory, Musk has a sense of style that places him a cut above many of his fellow execs. He looks great in a tux, has one or two killer pieces – like the Alexander McQueen velvet jacket pictured above – and knows when a Tesla graphic tee and Nikes will do the job.

Get Musk’s look:

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Alexander McQueen velvet and satin blazer,~$US828

Nike Lunar Flyknit HTM NRG, $US425

11. Evan Spiegel, CEO of Snap

Kimberly White/Getty Images for Vanity Fair

Evan Spiegel is no stranger to the fashion world. He’s graced the pages of Italian Vogue, talked about his must-haves with GQ, and he’s also married to model Miranda Kerr.

Spiegel has a specific personal style and great taste. He favours high-end sneakers and pricey t-shirts, and is on a constant quest “to find the perfect aviator.”

But Spiegel loses a few points simply because his choices are boring. He told GQ he’s been wearing the same t-shirts and sneakers since high school, and he rarely strays from some combination of black, white, and grey. While Spiegel always looks great in a young, hip, California-kid kind of way, it’s time to switch it up now that Snap is a high-profile public company.

Get Spiegel’s look:

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James Perse high gauge jersey tee, $US95

Common Projects Achilles low-top sneakers,$US415

10. Sheryl Sandberg, COO of Facebook

Jonathan Leibson/Getty Images for AOL

It’s tough to find a photo of Facebook COO Sheryl Sandberg either very dressed up or very dressed down. She seems to have one mode: Poised and professional.

Sandberg isn’t the most daring when it comes to fashion, but she knows what looks great on her and she sticks to it – she’s almost always wearing a form-fitting, solid-colour sheath dress and knee-high boots or pumps.

While it would be nice to see Sandberg branch out for her uniform, her choices are varied enough that she always keeps it interesting.

Get Sandberg’s look:

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Adrianna Papell crepe sheath dress, $US50

Michael Kors Janice boots, $US147

9. Kevin Systrom, CEO of Instagram

Dimitrios Kambouris/Getty Images

Instagram CEO Kevin Systrom is arguably the most put-together executive in Silicon Valley.

Systrom has rallied against sloppy dressing and has argued that people who make beautiful products shouldn’t be considered “indulgent” for also caring about how they dress. He always looks the part of a CEO, and he seems like someone who wouldn’t be caught dead in sweats.

Systrom, like several of his Silicon Valley peers, opts for pricey sneakers and slim-fit jeans most of the time. If I had to put a label on it, I’d define Systrom’s style as “nerd chic,” but that’s not insult – his buttoned-up, preppy aesthetic works for everything from casual outfits to a classic tux.

Get Systrom’s look:

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Nordstrom men’s shop marled yarn sweater,$US79.50

Lanvin suede and patent-leather sneakers,$US495

8. Jack Dorsey, CEO of Twitter and Square

Drew Angerer/Getty Images

Jack Dorsey has had one of the most dramatic style evolutions over the past few years, which is why he earns such a high ranking.

When Dorsey first hit the scene, he had long bangs and was prone to wearing button-down shirts tucked into jeans. These days, it’s a much different story.

While Dorsey’s style can veer dangerously into Yeezy Season territory, his affinity for a tougher aesthetic looks much cooler than his mid-2000s style. He’s rarely photographed without a leather jacket or Rick Owens shoes, and he tends to choose trendy, stylish formal wear.

Get Dorsey’s look:

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Everlane cashmere hoodie, $US140

Rick Owens Island Dunk high-top sneakers,$US1,115

7. Satya Nadella, CEO of Microsoft

Drew Angerer/Getty Images

When Satya Nadella first came on board as CEO of Microsoft, he was quickly lauded for his great sense of style.

While Nadella favours a lot of the same types of clothes as his Silicon Valley brethren like hoodies, polo shirts, and jeans, what sets Nadella apart is his eye for detail.

Rather than choosing a boring, basic pair of sneakers, Nadella wears high-end Lanvin shoes. Instead of a boring, basic polo shirt, Nadella usually chooses a shirt made out of a cool textile. Plus, Nadella’s clothes are always perfectly fitted, almost like they were made just for him. Other Valley execs should take some notes.

Get Nadella’s look:

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Neiman Marcus cashmere long-sleeve polo sweater, $US248

Salvatore Ferragamo patent leather low-top sneaker, $US530

6. Ginni Rometty, CEO of IBM

Paul Morigi/Getty Images for Fortune

You’d expect the CEO of IBM to be a conservative dresser, but that’s not the case with Ginni Rometty.

Rometty picks chic, beautiful clothing at every occasion, and she manages to look appropriate for the corporate world and extremely stylish at the same time.

Rometty’s royal purple coat paired with a patterned scarf while leaving the White House looks bold and stylish, while her leather jacket on stage adds an edge to a simple black dress. Rometty’s personal style is a perfect model for female executives in Silicon Valley – and beyond.

Get Rometty’s look:

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Harris Wharf London concealed single-breasted coat, $US423

Missoni ripple-stitch scarf, $US155

5. Angela Ahrendts, senior vice president of retail at Apple

Ilya S. Savenok/Getty Images for Fast Company

Before joining Apple, Angela Ahrendts led Burberry, so it’s not much of a surprise that she has a great fashion sense.

From the looks of things, Ahrendts has never encountered a trench coat she didn’t love. She has them in varying prints, colours, and materials, and usually pairs them with pants and high-heeled boots. The look really works for her, and helps her stand out in the Silicon Valley boys club.

Get Ahrendts’ look:

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Burberry macramé lace trench coat, $US2,895

Burberry buckle detail suede peep-toe ankle boots, $US695

4. Brian Chesky, CEO of Airbnb

Michael Kovac/Getty Images for Vanity Fair

Brian Chesky got his start at RISD, so it makes sense that he also has an eye for fashion.

The Airbnb CEO frequently wears clothes and shoes from designers like Gucci and switches up standard business-casual outfits by getting creative with fit, colour, and texture.

Chesky’s shoes in the top photo, for instance, are a mix between sneakers and boots, but they’re rendered in grey suede. Rather than a standard button-down shirt under his blazer, he opted for a collar-less version. And even his t-shirts are two-toned.

Another great thing about Chesky’s style is that as a former athlete and bodybuilder, he knows his body well and chooses clothes that look great on him.

Get Chesky’s look:

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Ralph Lauren men’s classic-fit neat ultraflex sport coat, $US59

Vince Abe suede sneakers, $US160

3. Arianna Huffington, CEO of Thrive Global and Uber board member

Paul Morigi/Getty Images for Fortune

Arianna Huffington is one of the most fashionably dressed CEOs in tech, and likely in business as a whole. Her choices are creative, on-trend, and almost always a little surprising.

The best thing about Huffington’s style is that she’s not afraid of new prints, patterns, and textures. She also plays with silhouettes, pairing full skirts with high boots or skinny pants with pointy-toe slingbacks. Huffington also clearly pays attentions to fit and appears to have a tailor on retainer. If there’s a closet worth raiding in tech-land, it’s Huffington’s.

Get Huffington’s look:

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Armani Collezioni lurex tweed zip-front jacket, $US417

Vince Camuto Armaceli over the knee boot, $US119

2. Jeff Bezos, CEO of Amazon

Drew Angerer/Getty Images

Jeff Bezos wouldn’t have been at the top of this list a few years ago, but he’s recently undergone a style transformation.

These days, Bezos can be seen in high-end sunglasses, slim-fit suits, tight t-shirts and polos, and cool outwear like vests and bomber jackets. While most people suspect he’s adopted a new workout regimen, he also appears to have taken an interest in how his clothes look and feel. Bezos is now the richest person in the world and these days, he actually looks the part.

Get Bezos’ look:

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Barbour essential gilet, $US149

Garrett Leight Van Buren folding sunglasses,$US365

1. Bozoma Saint John, chief brand officer at Uber

Craig Barritt/Getty Images for ADCOLOR Awards

By now, everyone knows Bozoma Saint John.

The former Apple exec – who’s now in charge of branding at Uber – first made a splash on stage at WWDC in a hot pink dress last year. Since then, her style choices have been equally eye-catching, unexpected, and often stunningly beautiful, making Saint John an obvious choice for the No. 1 slot.

What makes Saint John the best dressed exec in Silicon Valley is the fact that she doesn’t actually dress like she works in the Valley at all. Her outfits are bold and fashion-forward, and often have a nod to her Ghanaian roots through accessories like jewellery and bags.

As a young, female exec in a male-dominated industry, Saint John could easily feel pressured to tone it down and cover up, but she doesn’t. While her peers are ensconced in oversized hoodies and poorly fitting jeans, Saint John will show up in a skin-tight leather cat suit or a pink plunging mini-dress. She always seems to stay true to herself and her personal style instead of trying to fit in, and will hopefully encourage more women in the Valley to use fashion to express themselves.

Get Saint John’s look:

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Opening Ceremony faux-leather zip-front mini dress, $US325

Rebecca MinkoffLeo Saffiano envelope clutch bag, $US95

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