Dressing for Startup Life

The limitations of a “flexible” environment, and how gender diversity made me feel more comfortable being myself


When I started my job as the first woman hired at a tech startup, I hardly realized that I was suppressing my femininity.

I’ve always been the type to surround myself primarily with men; even in grade school, most of my close friends were boys. As I’ve grown older, one of the most important ways I’ve matured, at least by my own subjective measure, is that I’ve stopped feeling threatened by other women. In my two and a half years of working at a startup, I’ve had the chance to see what’s changed as we’ve improved our gender ratio. I feel more convinced now than ever that gender diversity is essential.

The question I want to begin to answer in this piece is:
“why do diversity and inclusion matter?”

How do diversity and inclusion add value to an organization? There have been plenty of studies about how different types of diversity affect workplaces, many of which point to positive effects for both company culture and bottom line. I’m going to take a more anecdotal and theoretical approach, analyzing how increased diversity affects office attire. When we’re more comfortable being our authentic selves at work, we can work, create, and communicate better.

If you’re looking for an exposé about a company that’s doing all the wrong things, you should stop reading, because I can honestly say that I like my company. I respect and trust the people here, and we’re having a lot of awesome, productive conversations about how to foster an inclusive environment. If I felt differently, I would write a more scathing piece and publish it anonymously. On the other hand, I really don’t want this to come across as some sort of PR puff piece. No one put me up to writing this, and as far as I can tell it’s coming from the heart. We have things that we could be better at, too, but I can’t cover everything in a single article.

While attire is largely a surface-level choice, it can also serve as a battlefield of self-expression, an outward display of underlying values. Many workplaces have imposed strict rules around attire. Uniforms sit at one end of this gamut, imposing complete homogeny.

Somewhere in the middle lie companies that make very specific suggestions or rules about dress code without providing default attire. For example, many corporate and retail settings have highly codified dress codes. A few years ago, American Apparel’s dress code stirred up discussion, and this NY Mag article sums up some other retail dress codes in light of that conversation.

On the other end of the spectrum is the tech startup world, where many companies don’t have any formal dress code whatsoever. In these environments, employees are expected to make their own judgments about what constitutes “proper” work attire, and sanctions (both social and professional) are nearly as severe for being overly formal as they are for being wildly inappropriate. In general, I’m in favor of these flexible dress codes, and one thing I’ve noticed at my workplace is that the range of attire here has increased with our gender diversity.

In his 2006 book Covering, Kenji Yoshino draws from classic sociologist Erving Goffman to summarize the process of cultural assimilation in three stages, drawing from his personal experience as a gay man. Conversion is the stage at which a marginalized person is expected to change who they are (for example, a gay “recovery” camp). Passing “pertains to the visibility of a particular trait” [18], requesting that we hide who we are (for example, being gay but appearing straight). The final stage, covering, “pertains to [a trait’s] obtrusiveness,” requesting that we don’t overemphasize a particular part of our identity (for example, identifying as gay but not acting “too gay”).

As a woman in the workplace, I’ve never been asked to convert to or pass as a man. However, I did find myself, in the early stages of my employment, inclined to “cover.”

This was never asked of me by anyone, but by instinct, I sensed that I would have an easier time being accepted in a company of men if I downplayed my femininity. I wish I could have been more like Genevieve Bell, social scientist at Intel, recently featured in the New York Times, who took the opposite approach:

“Even her appearance is a self-conscious provocation. In a corporate culture engendered by male engineers, and still dominated by them, Dr. Bell sees flaunting her otherness as part of the job description. “Some things I do quite deliberately… I wear French perfume. I wear heels. I dress like I am actually female.”

I was neither courageous nor secure enough when I started my job to emphasize my femininity to that extent (nor does extreme femininity really suit my personality). Instead, I sought the safe medium where my attire was neither frumpy nor overly feminine, the classic double bind. Over time, I became more comfortable dressing “quirky,” through unnatural hair colors or colorful tights, but I didn’t aim for the feminine side of my attire to ever be a topic of conversation, instead emphasizing the “fun” side of my appearance in relatively gender-neutral ways.

With no other women in the office, the only model I had for what was “acceptable” was what the men around me wore. Sweaters, quirky t-shirts, and boat shoes were good choices (and screw it all, I still like my black yacht-goth Sperry Top Siders). It’s hard to know where limitations stop and start in an office environment where there aren’t formal rules. For example, you wouldn’t want self-expression to become offensive or seriously uncomfortable (although I’m sometimes a fan of mild discomfort—how else would we grow?). In a “free” environment, how are cultural rules enforced? Is it safe to rely entirely on social sanctions?

A friend’s former workplace imposed a rule that employees could only compliment one another on their hair, never on anything else appearance-related, including clothing. Presumably, the goal of this rule was to negate sexual tension in the office (we won’t talk about how many sexual things one could say about hair). This is a common argument for limiting workplace attire.

Obviously, sexual tension isn’t a goal for an office environment, and “sexy” will never be the first adjective that I personally aim for when dressing for work. If the goal of dressing more freely isn’t to increase one’s sex appeal, then why does it matter?

Yoshino, in Covering, writes, “My ultimate commitment is to autonomy as a means of achieving authenticity, rather than a fixed conception of what authenticity might be.” Goffman writes of “facework,” the conscious efforts that we make to manage our identities, and it’s called “work” for a reason. Most of us would agree that we expend more energy when we’re molding our “authentic” self to a specific environment to fit in, instead of allowing that self to manifest naturally, outwardly. Attire is the most basic place where this self-expression occurs. The Goffmanian “frontstage work” of putting on a particular face at work is exhausting:

“When a line [verbal and nonverbal actions that are indicative of one’s particular point of view] and internal image of one’s self are harmonious, one’s said to “have,” “be in,” or “maintain” one’s face. Feelings of security and contentedness result from feeling as though one is in face. Subsequently, feelings of confidence arise when one can maintain face successfully.”
—Erving Goffman quoted via this social theory wiki

To me, the optimal work environment is one where minimal energy is spent performing — where one’s most essential, inner self aligns, rather than conflicts, with a self that is seen as respectable and professional. The less energy is spent performing and covering, the more energy can be dedicated to the work at hand. Marlena Fine writes, in Cultural Diversity of the Workplace: The State of the Field:

“People who spend significant amounts of energy coping with an alien environment have less energy left to do their jobs. Assimilation does not just create a situation in which people who are different are likely to fail, it also decreases the productivity of organizations.”

What are we after when we say we want a more “diverse” workplace? Our team now includes 9 women out of 24 employees, not to mention a wider variety of personalities, life stages, and interests. In my particular experience, I’ve felt much more able to dress freely at work as we’ve hired more women.

This new freedom isn’t limited to the realm of clothing. The more difference is present, the more comfortable each individual feels deviating from the average in novel ways, leading to more creativity in the organization as a whole. We’re more able to express our distinct tastes, feelings, ideas, and history. We’re less afraid to share our unique solutions as we solve problems together. As my coworker Brendan succinctly put it in a conversation we had a month or two ago, the more different we all are, the more aware we’ll become of what we truly share. Kenji Yoshino made nearly the same point in Covering: “Ironically, it may be the explosion of diversity in this country that will finally make us realize what we have in common.” [192]

The less compelled we feel to cover, the more freely everyone in an organization is able to express themselves. More importantly, in an environment where covering is at its necessary minimum, less energy is spent on these efforts to assimilate, and more energy can be used to solve problems creatively and communicate openly with one another. Beyond the moral and cultural benefits of being able to feel more human and fulfilled, this wider range of ideas can benefit business as a whole, ensuring that more smart, qualified voices are accounted for to build products that benefit a greater portion of society.