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This fall, many companies began sending out “return to the office” emails. They likely offered a tentative road map for mask-wearing and lunch protocols. What they probably didn’t address is a question that’s top of mind for many people who’ve spent two years working from home in sweatpants: What on earth am I going to wear?

“It’s going to be quite a dilemma,” says Soo Min Toh, associate professor of organizational behaviour and director of the Institute for Management & Innovation at the University of Toronto Mississauga. Even though we’ve all gotten used to seeing colleagues in T-shirts instead of suits, it’s hardly a certainty that workplaces will – or even should – make the casualization of office wear permanent.

One thing that is certain though: What we wear to work does matter, whether we like it or not.

“Appearance is the first thing we notice about people,” Dr. Toh says. “From there, we draw all sorts of cues, like whether they are competent or conscientious.”

That’s a concept we may not be comfortable with – after all, competency has nothing to do with whether your waist is elasticated or not – but the fact remains that you are being judged for what you wear, and you’re probably judging others too.

Creating a new set of expectations

Dr. Toh points to the psychological concept of “prototypes,” meaning we all have subconsciously formed notions of what certain types of people should look like. It’s the idea that scientists wear lab coats, for example, and Zuckerberg-type “geniuses” wear hoodies.

“[The more] you fit a certain prototype, the more likely you are to be seen as someone of that group,” she explains. “This is where we get this idea of ‘executive presence,’ where you need to come across as an executive in the way you look and talk.”

Dr. Toh says these symbolic codes can actually function as a tool, allowing someone who may not normally fit the prototype to look the part.

“But it’s a tool within a system that has [particular] expectations,” she notes. For example, women in Silicon Valley who wear hoodies like their male counterparts may be perceived as incompetent rather than uber-talented.

This is why Dr. Toh is hopeful that the experience of the pandemic – which has demonstrated that productivity and wearing a blazer aren’t correlated – could create a new set of expectations and a larger rethinking of the work force.

“It’s an opportunity for [organizations] to show that they care about their people,” she says. A dress code change could be a “symbolic move to signal a change in the organization’s approach and values.”

For women, who often spend more time, effort and money on “office appropriate” attire and grooming than their male counterparts, that may sound like a welcome shift. But whether a company decides to return to a traditional dress code or embrace sweatpants, it’s important that they make this change official, say Sarah Saska, co-founder and CEO of Feminuity, a DEI consulting firm that works with companies around the world.

“This overarching shift to the more casual dress code has translated for a lot of companies into just throwing their dress code out the window, and they’re not replacing it with anything else,” Dr. Saska says. “If companies don’t design these policies in a really deliberate and intentional way, often unofficial cultural rules emerge from [employees], and the chances of them [forming] along sexist, classist, ableist or racist lines are very likely.”

‘Another kind of prison’ for marginalized people

In the absence of official guidelines about what may be acceptable, marginalized people in the work force may “over index,” says Dr. Saska, and actually be even more formal than before.

“If you look at that ‘new casual’ aesthetic, especially for women, it follows very white, nondisabled forms of dress,” she says, pointing to the cashmere sweaters and pricey leggings that often form part of this uniform. “If less formal dress codes are to become truly equitable, the association with casual dress and competency has to be part of the conversation, otherwise people are going to try to protect themselves by how they dress.”

In attempting to create freedom, companies may accidentally create just another kind of prison for their employees, she says. “When companies say they want their employees to dress as their ‘most authentic self,’ that’s so wildly wrapped up in privilege.”

If an organization wants to do it well, Dr. Saska recommends they “put it to their people,” and get their input on a new, post-pandemic dress code.

“Treat it like a design challenge. Ask [questions such as]: How does sexism show up in the dress code? How does the exclusion of non-gender conforming and non-binary folk show up? How do ableist notions show up? It’s a matter of taking a decolonizing and inclusive lens, and collectively designing that policy.”

It’s a dressing code of conduct rather than a rule book, one that purposely solves for things like “stigmatization around hair” or “sexualization,” Dr. Saska says. (You can’t allow yoga pants without addressing the ways women’s bodies can be perceived, for example.)

She adds that any new code should also acknowledge the ways that these two years have changed many of us, especially if someone’s old default work wardrobe no longer fits who they are now.

For example, people may have transitioned or may have been “playing along the gender spectrum” in their time away from the office, and so may show up looking a lot different upon their return.

If workplaces don’t thoughtfully consider these sorts of issues, says Dr. Saska, the risk is that “some people might regress or ‘mask’ again, when they’ve been able to blossom while remote.”

Ask Women and Work

Have a question about your work life? E-mail us at

Question: I’ve been crunching the numbers and I’m thinking about making my side hustle into my main livelihood. But I’m a single mom and I’m worried about taking the risk and quitting my job. But there is no way I can continue doing both my job if I want to give my side hustle a chance to grow. I have some savings and that would realistically cover my expenses for six months. What are the steps I should take before I quit my job to optimize my chances of success?

We asked Neha Khera, general partner at 2048 Ventures, a “thesis-driven earliest stage” venture capital firm, to field this one:

What an exciting place to be in! It sounds like this side hustle of yours is really starting to take off. The beauty of running your own business is that the upside potential is limitless. The downside is that it’s a big risk. And I agree that if you want to do it well, you’ll have to jump in with both feet.

Some practical advice as you think through this decision:

  • Are you providing a product or service which is filling a need in the market (customer discovery)?
  • Is there enough of a market for your product or service to sustain your lifestyle (market size)?
  • Do you have a good understanding of how to ramp up revenue and number of customers (sales)?
  • Will you need capital for your business and, if so, have you identified how to source it (financing)?
  • Are you prepared for the emotional ups and downs that come with running your own company (HR)?

If you’ve got a good handle on the above, then it really boils down to your risk appetite. I suggest setting some tangible goals for yourself and reassessing them after three, six, nine months. For example, obtaining ‘x’ dollars in revenue or acquiring ‘x’ new customers by a certain date. Hitting or missing these goals will be a good indicator of whether to keep at it.

In general, entrepreneurship is equal parts exhilarating and terrifying. I commend you for reaching this point, and I think that if you can support yourself for a little while to give it a shot, then go for it. You’ll never know unless you try. Good luck!

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