Dress for Tech Success

If you were creating a time capsule of business books, I’d vote to include Dress for Success, by John T. Molloy. Written in 1975, the book helped reverse a trend that had begun a few years earlier: That is, until then, each generation showed the next one how to dress. Dads helped sons tie Windsor knots, and Moms helped daughters with proper hems. Sadly, the hippie era inverted this process, and grown-ups starting dressing like their kids. (Remember Dad’s awful fat tie in 1973?)

You might think this an unusual topic for a cyber security column – but perhaps you should know that I spent a decade earlier in my career helping my wife with her bridal and tuxedo shop. After a day of Unix Security at Bell Labs, I would drive to our store in the evening to play haberdasher. I’d drop a tape measure around my neck, and would spend the evening helping customers select their full black dress, formal shoes, and the like. I even did alterations. (Badly.)

Now, after retiring recently from AT&T as CSO, I made the decision that my hip new cyber security start-up company, TAG Cyber, would operate out of a sleek WeWork in Manhattan. And so, over the past year, I’ve had the opportunity to observe the sartorial habits of literally hundreds of young people – almost all in tech-related jobs. Perhaps worse, I’ve had the discomfort to watch many more experienced (ahem) tech workers select some pretty questionable dress options.

So, as a holiday offering to my friends and readers, I’d like to provide three basic rules that you are advised to heed when creating your look before hopping the 6:15-to-Hoboken. These are rules that come from decades of experience as a telecomm executive, bank director, application programmer, university professor, network designer, firewall engineer, keynote speaker, and tech consultant. They are rules that apply equally well to both women and men.

Let’s start with the most important of the three rules: Dress to show respect for others. When you interact with peers, managers, or customers in tech – or any other industry – it is essential that your dress selections make those around you feel comfortable. It is not acceptable to use dress to demonstrate how smart you are. That Android kernel expert wearing sweat pants and a Steelers jersey during the design review does not look like a genius: He looks like a slob.

Here’s a story: I was in a meeting in Washington not too long ago with a group of Meet the Press-type famous people. It was a formal meeting in a formal setting, and our critical infrastructure topic set a serious, grave tone. I wore a navy suit with black shoes, white shirt, and red tie. Other attendees were either in military dress or something similarly conservative. If you close your eyes and imagine the room, you will be 100% accurate.

Anyway, about halfway through the meeting, a famous tech person – one you would recognize immediately from the Internet – showed up about 30 minutes late, disrupting the flow of the discussion. As he noisily made his way to the table, I saw that he was wearing a tee-shirt with his company logo on the front, wrinkled jeans, and Crocs. Ugh. Now, I know this tech executive to be smart and capable, but at that moment, I could only think of one word: Jerk.

My advice for anyone reading these words is to think carefully about those who will be around you during your work day. Sure, if you’re going to be crawling under lab desks pulling wires, then dress accordingly. And if you are going to be sitting in your cubicle taking calls all day, then wear something comfortable. But this all-too-common view that you should wear whatever you want is wrong: You should dress to show respectfor those around you.

The second rule of dressing for tech success is a conservative one: When in doubt about what to wear, then dress up, not down. I know this is heresy for all my DEFCON hacker friends, who would sooner turn in their Macs and iPhones, then put on a clean, collared short with a pair of properly ironed and fitted Khaki pants. But when they arrive at a meeting wearing an ill-fitting EFF tee-shirt, it makes grown-ups like me uncomfortable. If that’s the goal, then it’s working.

Here’s another story: I was at a small training conference recently where the group of attendees were told in advance to wear business casual. And we did: Men wore jackets and collared button-downs, and women had on comparable business attire. Our morning speaker was a well-known tech founder, and he had been invited to offer thirty minutes of guidance on our industry. The event was in a typical conference room.

Anyway, the expert rose to greet us wearing wrinkled jeans, dirty sneakers, and a rumpled shirt. I thought he looked like a graduate student who just crawled out of the library after an all-nighter. Normally, I’d shrug this off and just listen to what he had to say, but this guy spent the first ten minutes scolding us for what we were wearing! He told us that Silicon Valley is jeans-and-tees-only, and that if we wanted to be successful, we should reconsider our dress.

Look, if this guy was speaking with my Stevens or NYU students at a pizza lunch, then his clothing was perfect. But to come to this business casual event wearing something off-the-charts sloppy, and to then make us feel even more uncomfortable by criticizing our dress – well, I must say that he was being a bigger dress snob than any Wall Street banker wearing even the silliest looking Michael Douglas suspenders.

So, keep in mind this second rule: When in doubt about what to wear to a meeting or event, dress up – not down. If you are a man, and you’re attending a machine-learning demo or a marketing presentation, then bring along a jacket, even if you’re wearing jeans. You can always set the jacket on the table if you’re overdressed. And if you are a woman, then don’t fall into that trap of looking like you’ve been summoned to haul PCs on a hand truck into the lab. Dress up, not down.

My third and final rule for successful tech dress will violate the belief system of every Millennial who might be reading these words. Here it is: Learn to emulate the look and decorum of grown-ups – preferably those who are at least a generation your senior. This might come as a jolt to twenty-somethings who were told to believe in themselves, and to follow their own personal guidance navigators. But it is sound advice.

For this problem, I blame technology. That is, if you are a Millennial, then you grew up believing that nothing in the galaxy was more important than technology. And since youngsters are naturally more fluent with apps and port scanners and mobile devices then their parents, they tend to extrapolate their tech superiority to everything – including business decorum. This is wrong, and parents need to be clear about this one to their children.

Here is my advice for any youngster who wants to be successful in a technology career: First, you should obviously be focused on your real technical contributions. If you read this column, then you know that I value deep knowledge and clever innovation in security and technology. So, yes, I’d sooner hire a true genius in sweat pants and soccer cleats than someone who looks and acts great, but doesn’t know a TPM from an ATM.

But if you want to be really successful in tech, especially in a larger company, then adopt the decorum of someone who is more senior than you. Find someone who dresses in a modest, but confident manner – someone who always looks comfortable, but respectful. And try to emulate that person’s decorum. Watch what he or she wears, and get over to Brooks Brothers, and plunk down whatever it takes to upgrade your look. (Use your Trump bonus.)

If all of this is new to you, then buy a copy of Mr. Molloy’s book. It’s been updated through the years, and I think it continues to serve as an excellent guide for anyone looking for an edge at work. It will be useful regardless of whether you work in a start-up bro culture, or whether you work in a stiff bank. Everyone will benefit by spending time focusing on the best elements of dressing for tech success.

Please let me know what you think of this (unusual) column – and Happy 2018 to you all!