by Raegan Thurlow, Part-Time Fashionista
Most of my generation will say that they remember where they were when Obama was elected president. I will remember where I was the first time I saw my CEO wearing jeans…
We were at the airport preparing to take an 18+ hour flight to our office in Tel Aviv, Israel. He was wearing a white t-shirt and light denim jeans. I was speechless – until I wasn’t. “What are you wearing?! What’s going on?!” It was unnerving. I’d only ever seen him wearing the slacks and business shirt combo his Nordstrom personal shopper had picked out for him. This new attire suggested that in addition to being the head of my company, he might actually be a human being. I felt dizzy, possibly even jetlagged (and this was pre-flight!). I was his assistant at the time and often wore jeans to our casual start-up office. But I was his assistant. I was allowed to be someone who existed outside of a boardroom.
I once worked at a company where the president (a very wealthy man) wore the same ratty sweater every day, hole in the elbow and all. Rumor had it he was on a lettuce-only diet, and his attire did nothing to dispel rumors that he was one bizarre individual. Neither did an email he wrote me containing only lyrics to Rolling Stones songs. But that’s for another article.
Steve Jobs was known not only as the genius behind all things “i”, but as the man always seen in jeans and a black turtleneck. Not only did he always wear the same thing, it was such an unfashionable choice. There should have been an app for that.
As for the fairer sex?
I’ve had female bosses with permanent VPL (visible panty lines), ones who only wore sleeveless shirts, one who refused to wear a bra, and on occasion, believe it or not, I’ve been forced to report to women who wore brown belts with black shoes. Sometimes you have to wonder if there’s a god/if people own mirrors.
Questionable behavior: wearing a “uniform” when you’re rich and could therefore wear the most amazing clothes on the planet. This just doesn’t make any sense to me. I’m nowhere near wealthy and refuse to even wear a laptop bag that isn’t Gucci. But maybe that’s just me.
Have you ever socialized with coworkers outside of the office, catching a glimpse of them in their outside-work attire? Someone you thought was a completely normal human being because of their work “outfit” turns out to be someone you’d label a “weirdo” if encountered in any other setting. We’re talking daisy duke jorts and flip flops. I won’t even get into what I’ve seen female coworkers wearing.
There is something utterly disturbing and image-shattering about successful tech people dressing like they don’t have a clue about style. What’s the point of having money if it doesn’t look like it’s pouring out of you? If you’re fortunate enough to be able to afford designer clothing, you’re really just spitting in the face of us fashion-hopefuls by not taking advantage.
So hey, tech CEO’s, it’s time to put down the hoodies and put on a collared shirt. You’re not fooling anyone into thinking you’re down-to-earth and approachable. And why would you want to? You’re successful, you’re smart, you’re rich. It’s time to “like” a new wardrobe.
I’m wondering if being sartorially challenged is an affliction particular to Silicon Valley executives. I recall shopping at the upscale mall in Palo Alto, and seeing all the men over 40 dressed like they’re auditioning for a part in “You’re a Good Man, Charlie Brown”: baggy t-shirts, shorts, and sneakers. Then again, one of the worst combos I’ve ever seen was in Texas: polo shirt, khakis, and cowboy boots.