These Are The Most Stylish People In Silicon Valley


This is part of the “Silicon Valley Insider” series, looking at the passions, hobbies, and pursuits of Silicon Valley’s tech elite. “Silicon Valley Insider” is sponsored by Mercedes®. Read more in the series »

Silicon Valley is decidedly not a fashion center. Think khakis, Birkenstocks, and Mark Zuckerberg’s hoodie.

But a few Silicon Valley executives run impressive companies and look good doing it.

Here’s our ranking of the most stylish people in tech:

14. Melody McCloskey, Founder and CEO of StyleSeat

McCloskey runs StyleSeat, a site that lets you find and book beauty professionals nearby.

13. Aaron Levie, CEO of Box

Levie is the CEO of multi-billion-dollar company, Box. He’s also known for his colourful kicks, which he frequently pairs with a sports coat. Here’s a close-up of his favourite shoes and equally bright socks.

12. Brit Morin, Founder and CEO of Brit + Co

Brit Morin runs a modern day Martha Stewart brand, Brit + Co. She gives a lot of creative how-to advice, and her creativity shines in her wardrobe as well.

11. Jeremy Stoppelman, CEO of Yelp

Stoppleman has nailed the sports coat and jeans look.

10. Tristan Walker, Founder and CEO of Walker & Co

Walker runs a grooming company; naturally he likes to keep up his appearance.

9. Margit Wennmachers, Co-founder of The Outcast Agency and partner at Andreessen Horowitz

Wennmachers was recently profiled in SF Gate and dubbed the “marketing guru” of Silicon Valley. She often has six-course dinners in her home for friends in technology and gives lots of CEOs advice — including what to wear to work.

Margit wennmachers

Flickr via dfarber

8. Ruzwana Bashir, co-founder and CEO of Peek

Bashir runs a travel company, and you can find her rocking flirty, colourful frocks. She’s seen here with April Dembosky of the FT.

7. Ilana Stern, founder and CEO of Weddington Way

Stern, right, runs a bridesmaid dress startup, Weddington Way.

Ilana stern Weddington Way

Ilana Stern via Twitter

6. Ali Pincus, Co-founder One Kings Lane

Pincus started a home decor retail site, One Kings Lane. She’s great at outfitting homes and herself. She is shown here getting married to Mark Pincus, CEO of Zynga.

5. Gentry Underwood, Founder of Mailbox

Underwood created email management company Mailbox and sold it to Dropbox soon after launch for ~ $US100 million.

Gentry underwood mailbox

Flickr via TechCrunch

4. Jess Lee, CEO and co-founder of Polyvore

Lee runs Polyvore, a way to discover and shop new fashion and beauty trends.

Jess lee polyvore

Flickr via TechCrunch

3. Jack Dorsey, CEO and Founder of Square

Dorsey is frequently cited for his style sense, but a few years ago, he had a much different look. His early Twitter days included a nose ring and T-shirts, not the suits and fedoras he wears now.

Twitter founder Jack Dorsey


2. Sam Shank, founder and CEO of HotelTonight

No hoodies for Shank, who runs mobile hotel booking company HotelTonight.

1. Marissa Mayer, CEO of Yahoo

Mayer has both an incredible career and fashion sense. She has a closet full of Oscar De La Renta and she recently did a big spread in Vogue.

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