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I Work at a Start-Up: Do I Have to Match Their Casual Uniform?

Fleeces, jeans, and T-shirts.

I work in the video game/tech industry in San Francisco. Everyone wears the same thing—the common jeans and t-shirt/plaid shirt/fleece—including my boss. As an avid reader of GQ and young professional, I'm wondering, what should I do if my boss dresses casually? While I do like to dress more formally, I also envy the simplicity of their wardrobe (much in the way that Mark Zuckerberg wears the same thing every day to not spend energy on a trivial choice) so I'm wondering if there's a middle ground?

Hello! I'm so happy to write to someone who is an avid reader and a young professional, you seem shiny and put-together and unflappable.

Alright, let’s start with the last question first: there is always a middle ground and I think that’s an excellent destination to trek to. A middle ground is a sound place to stand when you are figuring out how to be yourself in a reasonable, comfortable way. As an example, in the all-boys high school near me growing up, there was an intimidating and complicated social hierarchy, from John Hughes movie asshole to John Hughes movie little geeky brother, and they all split up into different houses for beach week. The beach house where the guys seemed most chill and inclusive and cool enough was called "middle ground." Wait… it might have been called Middle Earth which is a Lord of the Rings thing? I consciously refuse to both confirm with anyone from high school nor the internet re: Lord of the Rings but, here we are. It was the place where people seemed most like themselves. You should locate a middle ground when you are figuring out how to be yourself in a new environment or a time of transition.

Regarding the intricate style tips of a sartorial middle ground for the office, I know there's a stylish magazine about this. The name slips my mind, but I can vouch for it. Let’s talk about adjusting to a new work environment, where you feel different and uphold unusual priorities. For this question, I turned to a men’s fashion aficionado who works at a tech company. In a dress-down office, there is a lot of silver-flecked woven lining. There is more room for creativity in a start-up environment, he says, “a casual workplace gives you a lot more leverage than anywhere else.” Then he said a bunch of fantastic words like chambray, sneakers, no socks, and slightly beat-up oxfords.

When a place has a full uniform, as you write, it’s appealing for its ease and as a way to fit in. Humans are pack animals and also lazy. We are wolves, but sleepy ones who usually need other people to catch our meat. This fashionable-tech man too described the seduction of a casual-grey-shirt-uniform, or as he put it: “a siren's song of elastic waists and baggy shirts.” Still, his well-dressed manner is part of his identity. He warns that you're going to stand out. He gets comments, some underhanded compliments or ribbing, but mostly compliments (“that’s nice”). And it's important to not cluelessly ignore the work vibe and dress like you're going to an entirely different party. “If you're new to the flock, that may be a bad foot to start out on,” he says, “heaven forbid you earn a workplace nickname like the Suit Guy.”

Take cues from your superiors about the vibe of the offices. Work with that. Imagine that you wouldn’t look out of place together in the same spread on a magazine page, but you’re just the more formal option.

Encouraging news also comes from the annals of Science. The Association for Psychological Science recently wrote about your exact situation, highlighted by the wonderful people at Science of Us: People who ignore the office uniform are seen as more competent at their work. This is called the “red sneakers effect.” It basically proposes that when someone dresses differently it shows a nonconformist attitude that highlights “high levels of autonomy and control,” according to the Harvard Business School study. But as always, when you're diverging either in the more slovenly or more dapper direction: If. You. Stand. Out. You. Should. Make. It. Look. Intentional. It can’t be that you just don’t get it or that you haven’t ever done laundry. It should show that this is your personality and you are confident in your differences.

Deciding consciously whether to dress more formally than your boss is intriguing—because that visually messes with some old-school power dynamics. But aren’t you guys disrupting over there? Didn’t Jesse Eisenberg wear shower shoes as a power play in a movie? Up-is-down and informal-is-weighty: I think this gives you permission to do your thing. Our different priorities and different ways of thinking make us valuable. Obviously hold onto that.

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