For the second year in a row, Bustle is bringing you Rule Breakers, a celebration of women and non-binary individuals who defy expectations at every turn — and are making the world a better place for it. As a lead-up to our Rule Breakers 2019 issue launching Aug. 27, we’re bringing back some of our favorite pieces by and about those who refuse to do what they’re told. Because challenging the status quo isn't just a once-a-year thing, it's an ongoing mission. These stories prove it.
Two years ago, when Emily Osowski was starting a job as a software engineer in New York City, she had to seriously reconsider her wardrobe. The 27-year-old Austin-born Brooklynite lived in vintage tees, perfectly beat up denim, and platform boots that added inches to her petite frame. But the vibe of her new office was decidedly more business formal, so she sucked it up and bought 10 pairs of J. Crew pants, half as many blazers, a smattering of tailored blouses.
Osowski played the part well, and coworkers would comment on how cleverly she managed to sneak a little bit of her own unique style into the corporate uniform. Still, throughout the duration of her employment with the company, she found getting dressed for the day pretty painful.
“It was a constant struggle for me — kind of like an identity crisis,” she tells Bustle. She felt like she was wearing a costume, and dreaded running into someone she knew on her commute, lest they become acquainted with this imposter version of herself. Osowski also thought that being unable to wear her “real” clothes kept her from really getting to know her colleagues. “It was like: This is not me, this is not my style.” she says. “How are these people going to understand who I am if I can’t express myself through what I wear?”
If you think this sounds like a particularly millennial kvetch — you’re not wrong. For the generation raised on the ideals of authenticity, individuality, and the right to self-expression, personal style can seem less like a workplace perk than a fundamental right. This is partly because millennials grew up in the era of overnight startup millionaires clad in hoodies and sneakers, who proved that you don’t have to look like a CEO of yesteryear to build a lucrative business. We — yes, I count myself among this cohort — are comfortable with the idea that what you wear and what you do don’t have to be entwined: It’s totally possible to be a #girlboss while wearing a crop top.
At the same time, our lives have been rocked by social, political, and cultural movements that have made us reconsider what success not only looks like, but what it actually means. For many, that requires questioning the racist, sexist, capitalist systems that have paved the way for millennials to become the first generation in recent history who are likely to be worse off than their parents. We have less money, more anxiety, and murkier futures; and, in the age of constant connectivity, where the office is everywhere within cellular range, it’s no wonder we don’t want to cede control over our wardrobes to our employers, too. As Osowski put it: “We already have to be at work for 8 or 9 hours, 5 days a week, and we shouldn’t have to put on a show and be uncomfortable for that amount off the time. Can we at least be able to feel like ourselves?”
According to many women Bustle spoke with for this story, the answer to that question was resoundingly: yes. The right to wear what we want is considered by some an inherent tenet of new feminism. On the other hand, living in the era of “anything goes,” from sequins and Tevas to athleisure and bubblegum pink double-breasted power suits, isn’t necessarily easier. Workwear expectations still exist. It’s just that now they’re often written in invisible ink — and the perception of sartorial freedom itself is, in some ways, a double-edged sword.
The dress code at Goldman Sachs can be boiled down to “mostly black,” Julianne DeMarco, 30, tells Bustle. When DeMarco started her career at the financial giant, no one explained what she was expected to wear; she was just supposed to figure it out herself. Call it a kind of test. DeMarco passed, stacking her wardrobe with Banana Republic suits, blazers, and black closed toe heels. “I worked with mostly men, so I wanted to make sure I looked as formal as they did, which is kind of hard without wearing a full suit,” she explains.
“The expectation was business formal. But what does that even mean for a woman?”
But she always felt stuffy. Plus, “The women who were matching them were not wearing two piece suits — they were wearing a variety of fancy, very well tailored outfits,” explains DeMarco. The costs of keeping up, from no chip manicures to blowouts and beyond, can get pricey. DeMarco fretted over the details, knowing that men weren’t being subjected to the same standards. “The expectation was business formal. But what does that even mean for a woman?” she wondered.
Women have been asking that question in some shape, form, and syntax for the last century — and, to be honest, we still don’t have a wholly adequate answer. The first time that women entered the modern workforce en masse was in the 1920s, around the time of World War I, and following the passage of suffrage; the sartorial options for women then were relatively limited, which, according to Deirdre Clemente, a cultural historian and author of Dress Casual: How College Students Redefined American Style, meant that in work environments coming to newly include women, dress codes were less likely to be written down. What to wear was more of an implied understanding — and one with a uniquely gendered edge.
“Dress codes are people in power trying to control other people’s dress. And most of the time, it’s men trying to control women’s bodies and choices,” Clemente tells Bustle. That proved true when, in the 1930s, advancement in the fashion industry around what we would today refer to as ready-to-wear gave women a wider breadth of versatility in their closets; in direct response, dress codes began to become formalized, written down on paper, with definitions of was appropriate and what was not allowed, authored by men whose biggest daily wardrobe challenge was putting on their pants one leg at a time.
Throughout the 20th century, this push and pull persisted. The options for women’s fashion would expand, and the (overwhelmingly male) powers-that-were would tighten the rules on how they thought women should dress. Cultural shifts played a part, too: During World War II, when men went to war and women went to work, practical clothing flourished (although red lipstick was seen as a woman’s patriotic duty no matter what she was wearing); in the ‘60s, when young women started to eschew nylons and hats for less buttoned-up attire, rigid rules made a return.
“I never wore open toed shoes before, but now if I don’t wear more casual stuff I feel weird.”
In the late ‘70s — prime time for the women’s liberation movement — a guide titled The Women’s Dress for Success Book claimed to have unlocked the scientific secrets of what women should be wearing at work: Blouses that we “too frilly” were a no-no, as was anything that the author, James T. Molloy, deemed to be an “imitation man look.” (One takeaway: Never, ever, ever wear a fedora, ladies. He also suspected that sexism might be one reason that women made less money than money. “But another reason is totally the fault of the women themselves. Many of them dress for failure.” Thanks, dude.)
Things changed in the ‘80s though, as tech companies set up shop in what would become Silicon Valley, they also set the tone for business casual — a look that has come to define our modern workplace, but which, at its core, largely left women without much guidance. Old norms about what constituted professional clothing were being reworked; geek chic was en vogue on the West Coast, while power dressing (including shoulder pads that could double as flotation devices) began to dominate Wall Street. But the problem with the relaxation and revamping of retro but clear dress codes was that the new rules largely left women fumbling in the dark. They weren’t making the rules, nor were they being told how to follow them. It’s a lack of clarity that has been improved today — but, in a lot of corners of the work world, continues to persist.
DeMarco has witnessed it in her own work wardrobe. These days, she is between semesters of her MBA, and interning at Bloomberg, where the dress code is less formal. “I struggle with this far more because there’s more flexibility,” she explains. “I never wore open toed shoes before, but now if I don’t wear more casual stuff I feel weird. My wardrobe was kind of geared toward the Goldman-vibe, whereas here, it’s far more creative and colorful. People sometimes wear jeans, but they aren’t totally casual. You could wear sandals if they’re nicer. It’s far more grey in terms of figuring out what’s appropriate.” Eight weeks in, she’s still struggling.
“If a company invests in its employees, I think you can see across the board that they tend to dress better.”
Sometimes the challenge is less knowing what to wear than having the motivation to put in the effort in the first place. Emily Cash, 33, tells Bustle that earlier in her career as a media buyer, she loved getting glammed up before work — it somehow made all the time she spent buried in spreadsheets feel more creative — but when, in her next job, she realized that she was being underpaid, suddenly she didn’t care as much about how much effort she put in.
“You can kind of correlate the decline of my professional appearance to the diminished feeling of being valued,” says Cash, who did her Masters of Science in finance at UT Austin after leaving New York City. Her explanation: “As a whole, millennials are grossly underpaid. If we’re lucky we’re getting cost of living increases and that’s it. People complain that we job hop too much but it’s the only way, in order to get sustainable salary increases. You always lie about what you’re making, because that’s the only way that you actually make increases in your income. I think that feelings of being underpaid and undervalued in some ways correlates to the way we present ourselves in the office. If you’re not doing any 401K matching, why should I look nice?”
Now in a new job, Cash finds herself once again attentive to how she presents herself: She likes getting up and getting dressed. “Even though we have a very casual dress code — they say you could wear ripped jeans, you could wear sweatpants if you want to — nobody does.” She thinks it’s because the culture at her office makes the people who work there feel valued. “If a company invests in its employees, I think you can see across the board that they tend to dress better.”
Leah Ring, 32, a Los Angeles-based interior designer who started her career in the advertising world (and is, full disclosure, a friend) tells Bustle that, in her industry, it’s not the level of casualness or formality that defines the “right” mode of dress but rather that ineffable “cool” factor. Coming from women’s media in New York City, that’s something I uniquely identify with when it comes to my own work wardrobe: I remember when, in my younger years, I asked a colleague wearing what I thought were just high-top Converse with a cute little red heart on them about her shoes. Before that conversation, I didn’t know that Comme des Garçons was a brand I needed to know about. Now, at 31, there are certain brands that I wear to certain meetings with certain people — low key, high price, cool girl clothes that communicate membership in particular in crowds. These are not rules you would find in a handbook, but they govern my dress decisions all the same.
“Millennials can take away the rules, but there is always a silent cultural standard to which women will be subjected.”
Here is a short story about how things change: Not so very long ago, women were not supposed to wear pants. Then, more women wanted to wear pants, because pants were comfortable and convenient. So they did. Plenty of other people (mainly men) were mad about the pants-wearing women. But the women kept wearing pants anyway! Eventually, fury subsided, and women in pants became a normal thing that no one bothered to question. Now, women wear pants all the time.
In other words: “All cultural barriers erode because people just do what they want, and the cultural barriers of what defines workwear are eroding,” explains Clemente. In a most basic sense, dress codes are just another form of people (usually men) trying to control other people’s (e.g. women’s) bodies and choices.
Millennials — raised on the Kool-Aid cocktail of individuality and personal brands built on Instagram — are particularly resistant to this kind of control. But though it’s tempting to think of dress codes are another one of those things millennials are in the process of killing — like mayonnaise or Applebee’s or golf — the reality is that not even millennials have the power to murder something that is so entwined with the way we think about identity. “What women wear is so laden with cultural meaning,” Clemente comments. “Millennials can take away the rules, but there is always a silent cultural standard to which women will be subjected.”
Annette Y. Harris is the founder of ShowUp!, a Washington, D.C. area-based personal brand and executive presence consultancy with more than a decade in the business. She says that getting women to live in the real world, instead of the ideal world, when it comes to how they present themselves can be challenging.
“Dress communicates whether or not you understand the cues about what to wear, and the culture of a place,” she says. But while younger generations don’t correlate “dress” with “success” in the same way as the ones who came before, Baby Boomers and Gen X-ers are still largely the decision makers in the work world — which means that, if you want to ascend through the ranks of a workplace, “dress for success” is still a phrase that applies.
“No one is going to tell you that you didn’t get the promotion because of how you present yourself.”
Furthermore, when women miss the mark — by dressy too edgy, too sexy, too frumpy, even too formally — they are judged by a set of standards that men would never be subjected to: If men are under the looking glass, women are being seen through a lens magnified by a factors thousands.
“Like it or not: Perception is reality,” Harris explains. People, and women in particular, are judged on how they dress, and whether or not you look like you can do the job still matters in most circumstances. In her business, Harris coaches companies to create more clarified rules around what employees should and should not wear, and also helps individuals develop their personal style that works for the office. “Today it’s not ‘dress for success’ so much as ‘dress for the day,’” she explains. And depending on how you spend those days, that can be tricky.
“In general, women today have more options, but that also means they have more opportunities to make mistakes,” says Harris. Dress code policies have evolved to become a list of “do’s and don’ts,” many of which tend to oversimplify things, all the while expecting employees to intuit nuance. Harris told Bustle about a business client that wanted to set down clearer guidance for how female employees should wear their hair at work. “How do you feel about ponytails?” they asked. “The I-just-got-out-of-bed-and-rushed-out-the-door kind of ponytail, or a sleek Kim Kardashian ponytail?” she shot back. Drawing out what’s okay — and where the lines fall — is as much an exercise in professionalism as it is in discerning the ways that we screen for capability.
Harris also says HR departments often want to keep discussions about the dress code light and breezy, in case the guidelines themselves become issues. “No one is going to tell you that you didn’t get the promotion because of how you present yourself. These are unwritten rules — it’s a test. And I have to tell you: A lot of people are failing, and not just millennials, either.”
Larissa Wocher, 31, works in the nightlife industry in San Francisco. Her job involves calling on clients and staying involved with the scene. Wocher tells Bustle that, for some of her colleagues, it’s not always easy to find the line between “going out clothes” and “going out and working” clothes. Recently, her employer updated the dress guidelines with visual elements that help delineate the difference. Harris is seeing other types of companies add photo imagery to their handbooks, too. It can be helpful, so long as it’s not overly simplistic. One example she gave me that didn’t work was a photo of a woman, clearly out at the club. “Everyone knows not to wear that,” Harris said. It’s the fine tuning where people have trouble.
“Being able to wear whatever I want has helped me connect with my coworkers more quickly.”
As for Osowski, not long ago, she left her corporate software engineering job and took on a new role, as a product developer at a hip marketing agency in Brooklyn. Before she started, she emailed them to find out about the dress code — not once, but several times. Each time, she got a nebulous response back that basically amounted to “you’ll figure it out when you get here.” After the last gig, that made her a little nervous, so she took care to dress up on the first day. When she got to orientation with other new employees, literally every single person was more casually attired than she was. It was a relief.
“I felt so much better. Being able to wear whatever I want has helped me connect with my coworkers more quickly — it’s been an easy topic of conversation and it’s made it easier to relax to people more quickly because we’re actually wearing what we want to wear,” says Osowski.
It’s also easier to go get a drink after work, because she doesn’t feel like she has to run home and change first. She’s more excited about going to work in the morning, to pick out her own outfit and see what other people are wearing. She donated the corporate attire to the Goodwill and is glad to have the extra space back in her closet. In the hours between 9 a.m. and 5 p.m., Osowski might be on someone else’s time, but she’s only ever in her own clothes.