Dressing for success as a woman in Silicon Valley

There’s a new class of perfect female executive in technology today. She wears short skirts, fitted tops, maybe a jacket or a small cardigan and heels. Always legs and heels. Her hair is perfect, her makeup light and she never forgets her lipstick.

These women were all over Dreamforce in San Francisco a few weeks ago. As I walked around the show I was struck by how much the uniformity of their look is the female equivalent of the buff, white sales guy of my early career who worked out as a part of his competitive regimen. His suit fit perfectly, his shirt was white, his hair short – the Don Draper of the 1990s.

Twenty years ago we (the women) were covered up. The admin could dress sexily in the office; professional women like me dressed in a strange male-mimicking style. Navy suits, cream shirts, shoulder pads with incredibly unattractive bows at our necks and sensible shoes. St John before it went Couture. Never a short skirt, that would be unprofessional. Never pants until the mid nineties. Combine that with early 1990s fashions and we did not look good!

But now, as women make up more than 50% of the workforce, and as women are gaining share of the executive ranks (albeit a little slowly, but it’s happening) the de rigueur dress code for professional women is smooth, polished, sexy and absolutely in control. Marissa Meyer, as the new icon of workplace style, revels in Oscar de la Renta. High fashion indeed.

The pressure’s on for women to look polished now. Consider Rebecca Jane Stokes’ piece in Jezebel yesterday “My Boss Told Me My Hair and Makeup Were Holding Me Back“. While I’m a CEO, and visible every day, I smiled as I read it because still find remembering the lipstick hard. (Confession: I think lipstick is pretty gross so maybe my subconscious is in control on this issue).

But lipstick is just one of many questions to ponder when you think about the time investment needed to create “the look”. What about…

• Hair dye? It takes an hour or more every 4 weeks to keep the color bright (and control the creeping grey!) Good use of time, or not?
• Nails? It takes 30 minutes every Sunday night to clean and polish my nails after an enthusiastic weekend in my garden. And the dog doesn’t like the smell so I’m doing it alone on the sofa.
• Hair? Blowing out my hair at home takes 30 minutes – and it’s every day because I swim almost every day. Leaving it “au natural” means unruly curls, not a sleek look. The really good look, for the very important meeting, takes 45 minutes at the salon. One of my friends who is a famous Silicon Valley female exec told me she never gives a talk without having her hair and makeup done for her. Never. That means 1.5 hours every time!
• Makeup? Another 10 minutes, so that’s not too bad, but it seems like a waste of time and effort to me. But I wear it for work, of course, though rarely outside of work.
• Heels? A clear sign of how hard a woman is trying. They are never comfortable but they do look good. But if you are presenting to your customer, or your investors, flats just never cut it, but stay away from FM shoes!

In the end I think the issue comes down to whether you are customer facing or not.

If you’re just in the office with your teammates then who cares! The studied nerd look of jeans and a t-shirt work well, although personal hygiene is still an absolute must. But if you’re on the outside representing your company then you need to look the part. At least professionally groomed and definitely clean.

Male or female, your brain and your skills dominate your ability to do the job. But meeting the threshold of expectation of your social group helps. It ensures you don’t get negatively, and unnecessarily, judged for how you look. If you’re in R&D or on the phone then jeans are accepted; if in person with a customer then professional is expected, and only when you know the customer well can you risk business-casual.

But for a woman that does not have to mean looking like the perfect clones. It means finding the professional look that works for you, your body type and your personality. Hillary Clinton proved that the pant suit can work at the highest levels of power. Meg Whitman has the dark suit and pearls down as CEO of HP.

The single most important thing is that you exude confidence in who you are – that’s what your team, management and customers need to see.