Top Silicon Valley Stylist Spills Fashion Secrets of Tech CEOs and Founders

Hoodies and jeans are out. Well-curated capsule wardrobes are in. Learn from Melania Trump.

Personal style is increasingly a big part of Big Tech for entrepreneurs and executives in Silicon Valley.
Personal style is increasingly a big part of Big Tech for entrepreneurs and executives in Silicon Valley. Sissi Cao for Observer

From Steve Jobs’ signature black turtlenecks (and his infamous imitator, Elizabeth Holmes) to Mark Zuckerberg’s everyday T-shirt-and-jeans look and his crisis-time apology suit, the physical appearance of tech CEOs is increasingly what people remember about them and, more importantly, their companies.

Putting together the right outfit for the right occasion is a challenging task and an inexact science at best—not to mention, it’s often not just about clothes and accessories, which is why many capable men and women in Silicon Valley pay professional stylists to fret over such matters behind the scene.

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“The consulting process is a delicate dance,” Victoria Hitchcock, a Bay Area-based fashion and lifestyle expert who advises Fortune 500 executives and tech founders, told Observer. “Both genders in my business clientele are insatiable learners. They are interested in the whys and why-nots; they want to be an intimate part of the process.”

Having worked in personal style advisory for over 20 years, Hitchcock lived through the first tech boom in the late 1990s and witnessed Silicon Valley’s evolving fashion sense first hand. In a recent interview with Observer, the seasoned stylist revealed what her clients want the most these days, what’s in and out of style in the Valley and her quick tips to look smart and put-together at your next business meeting.

Are there any basic style rules or principles you follow when advising a client?
The first step is the client assessment. We cover their perception of themselves physically and their five-year vision, both emotionally and where they want to be in their careers.

Sometimes we discuss their life stage and their level of readiness to improve. Once we identify this, we move on to thinking about creative ways to make a difference quickly. Is it clothing? Weight? A personal alignment or spiritual growth? A better sense of their aesthetic?

Sometimes what we reveal is revolutionary to them. It’s a quick hit that shows them where they are now and where we go next.

Does your consulting approach for male and female clients differ? How are their demands different?
Yes, a bit. Men are usually pretty direct about their goals and expectations. They’d say, “I’ve got a big gut,” and that triggers the direction I recommend. Men want deliverables, but they also want to understand the process and be involved—in the beginning, at least.

With women, I typically need to dig into their hang-ups—physically, emotionally or socially. What did their mother say about their lips? What was the mean nickname they were given in college, and why? Then, we consider the source of those criticisms and weigh that against reality.

Women are judged too much on their appearance. My goal is to make them comfortable, demonstrating their intellectual brilliance with a newly discovered smart style.

Women typically don’t mind looking completely different overnight, while men prefer gradual changes. My preference is gradual—a little goes a long way.

Victoria Hitchcock
Victoria Hitchcock. Victoria Hitchcock Style

Is the hoodie-and-jeans uniform out of style?
The hoodie-and-jean look came from the Silicon Valley recluses who yearned to look different than everyone around them on the corporate track in the Bay Area during the “loft” period, 20 to 25 years ago. It was the cool new way of expressive dressing for their creative work and workspace.

But now, wearing that hoodie-sneaker-jean uniform is almost conformist, so I recommend clients revisit their look and customize it to match their lifestyle.

What trends are people moving into? What’s in style in Silicon Valley now?
People are looking for comfort and practicality, the real issues of today’s tech executive. They tend to like items that have a lot of stretch and movement and materials that won’t get wrinkled during travel.

Right now, it’s all about the perfect fit. How a pair of pants fits carries more weight than the label attached to it.

They also want things simplified. It’s all about a well-curated, holistic approach. A capsule of aesthetics, function, lifestyle and image. Tech executives want to look sharp and effortless from day to night.

How important is hair?
Hair is huge. Whether a man has it or not, we can figure out how to set it up to make him look great. He could be almost bald and look as good as my next client who has a full head of hair. For women, it’s softer and natural, and short is making a comeback. Individual features dictate the best look.

What are the dos and don’ts men and women in tech should follow now? 

  1. Avoid scuffed leather shoes, whether they’re Adidas joggers or Prada loafers. Period.
  2. Wear your pants on your God-given hips, not two-inch higher or lower.
  3. No need to show your underpinnings. Men, hide the ratty or new T-shirt under the button-down, please. Women, I prefer not to see several layers of straps around the collar bones. Way too distracting.
  4. Men, take it easy with the multi-colored, patterned pocket squares.
  5. Your timepiece can make a subtle statement, but don’t let it wear you.
  6. Final tip for women: avoid black turtlenecks for a while.

Which business celebrities have the best styles, in your opinion?
Melania Trump is iconic—always dressed to the nines but respectfully for each occasion. She has a dynamic sense of color and dimension.

I also have a lot of respect for Bozoma Saint John [former brand chief at Uber]. Her ability to mix her colorful personality with a dash of femininity. I like that.

For men, Jack Dorsey is a favorite of mine. I call his image the “sensible-streamlined look.” Dorsey is spot-on. He has a very casual, practical and approachable look. He’s actually known to travel several miles daily by foot and takes his comfortable style from day to night.

Top Silicon Valley Stylist Spills Fashion Secrets of Tech CEOs and Founders