Four words. Back. To. School. Shopping. As a kid, I could always count on those four words to usher in a complete and utter feeling of dread and anxiety. Back-to-school shopping was positioned not just as the replenishment of school supplies in anticipation of the new school year, but also as the rallying cry to spend money on new clothes, new shoes, and new book bags. It didn’t matter if the clothes and shoes you wore last year still fit and looked good. It was of no consequence that your old book bag had nary a hole or tear in it. The expectation was that new is better; updated is preferred.

For the kids of well-to-do families, which my two sisters and I were clearly not, the back-to-school shopping season was met with excitement and glee. It was an opportunity to showcase the latest brand-name fashions and confirm your status as one of the popular kids. I didn’t even realize that we were “poor’ in this regard until the other kids were “nice” enough to point it out.

Due to a culture of consumerism coupled with the desire to fit in, the annual pressure to buy a new school wardrobe grew to be a source of anxiety for me and my sisters. My mom was a hard-working single parent who often struggled to make ends meet. There were many times when our family budget was constrained by more important matters such as eating, for example.

Despite all this, my mom always made sure that we were nicely dressed and that our clothes were pressed and clean. We had the best clothes that her K-Mart and Pic-N-Save money could afford. Sometimes, she would even splurge by buying us a few outfits from Diane’s Boutique utilizing their lay-away plan. Unfortunately, other kids also recognized our generic, non-branded apparel, and judged us accordingly. So you see, the seeds of “dressing privilege” (just like other forms of privilege) are sown early; the inclination to judge others based on attire is embedded early.

Today’s Dress Expectations for Work

“Dress for success.”

“Appearance is everything.”

“Dress the part.”

“Dress for the role you want, not the role you have.”

These are all statements that each of us has heard at some point during our career. On the face of it, they each make sense, but have you ever stopped to consider the stress or anxiety associated with these statements for those who have to heavily weigh practical considerations such as financial means? Desiring to dress well and affirm our place in our roles at work can leave us feeling anxious. Dress for success can easily turn into stress for success.

My millennial daughter works in the New York fashion industry, where the expectation is that she wear and represent upscale brand-name clothing and accessories. In reality, it’s a requirement coded as “expectation,” And though she is provided a clothing allowance and discounts to offset the impact on her budget, the cost of “expectation dressing” for her is exorbitant, especially in a city where she has to be concerned with expenses such as food, transportation, and the high cost of rent. Perform well, yes. But you must also look good.

As is everyone today, we are part of the most marketed-to generation in history, and the messages we hear focus on the new, the updated, instant gratification, materialism, consumerism, etc. How does this translate to the “unspoken” dress code at work? Some of us may get overwhelmed by and lured into a false narrative that we need more clothes, need new clothes, and need brand-name clothes in order to compete at work. The “keeping up with the Jones’ at work” or the comparison game can have real consequences.

The Dressed-Up Elephant in the Room

Because we apply spoken and unspoken dress codes and dress norms to ourselves, we then use them to judge others. We start policing the choices of others. Some of us even develop elitist attitudes about how we dress. And it’s not a far leap to say that these attitudes certainly don’t foster and support an environment of inclusion.

For example, few of us would dispute that women are more likely to be subjected to appearance scrutiny and judgment than are our male counterparts. Though it doesn’t seem necessary to provide support for this assertion, I can’t help but think back to my tenure as a cast member during the late 1990’s for the happiest place on earth and the handbook of appearance rules for men and women. The rules outlined for professional women in noncostumed roles greatly outnumbered the rules for professional men in noncostumed roles.

The long list of requirements and restrictions for women was at least three times as long as was the list for men. An unintended (perhaps) consequence of the numerous appearance restrictions for women is that these published restrictions succeeded in some minds in conflating women’s appearance with our skills, qualifications, and experience. Judging women became policy. In workplaces all over, women can be judged on multiple criteria up to and including attire. The result is language that codifies the judgment. Not a good fit. Lacks professional presence. Not compatible with company image. (And who could have imagined that “dress privilege’ would give birth to the “disposable clothes” phenomenon, a relatively new form of judging women for being seen wearing usually expensive, after hours special occasion garments more than once!)

Though to a lesser extent, this is not to say that men have been completely exempt from “dressing privilege” and the judgment it can bring. My husband, a former engineer during the late 1980’s at a consumer products company, describes how male employees were called “proctoids” because they all dressed, for the most part, in the same business suit “uniform” within the context of a rigid environment. For some of us, it may be easy to surmise that if they all dressed the same, then they likely fell under the psychological spell of thinking the same. Talk about the stifling of individual expression and the potential for suppressing creative thought!

Late 1980’s and late 1990’s. That was then, right? Have our underlying attitudes toward work attire changed all that much? Have our employers’ attitudes changed?

More Important Than the Clothes We Wear

Realistically speaking, many of us are bound by and have to navigate and honor a dress code at work. Employers are conditioned to have expectations of employees simply by looking at us. Employees are conditioned to dress in order to conform to the culture and norms established by our employer. Again, this can create undue financial pressure if an employee does not have the means to “keep up.” Some workers may not feel free to dress according to our true circumstance, which is based upon affordability, for fear of being judged. We make attempts to look good, before things become good.

The “good news” is that employers stepped in with casual Friday, dress-down Friday, business casual. Each was intended to free us from the anxiety and pressure of dressing in strict business attire and promote a more relaxed environment. On the contrary, what these “dress down” days succeeded in doing was creating the “need” for a new wardrobe that complied with the rules of business casual!

Consider the analogous and similarly ironic scenario of the vacation cruise. Though we may enjoy cruises, “dressing privilege” follows us onto the ship in the form of daily themed dressing protocols at dinner for which we are forced to pack required dress code clothing and bring with us. There’s casual night, dressy night, casual chic night, smart chic night, formal night. What happened to the peace and relaxation of our vacation? I’m sure most of us would just as well pack shorts, swimsuit, sunscreen, casual flats, and be done!

Wardrobe Staples That Hit the Mark

Yes, office politics may still focus on the external.

Yes, our appearance may be judged in seconds.

Yes, skills and ability to do the job should be the most important.

But that’s still not how it works. Until such time that our appearance is completely inconsequential, the way we dress should be a consideration. In reality, books are judged by their cover initially until we find out a bit more about them.

We can ease our anxiety by following the “rule of C’s” to guide our choices. Confidence by far is the best staple in our wardrobe, and recognizing it as such can bring great peace. Because no one likes to be feel overdressed or underdressed, adopting a balanced approach that errs neither too much on dressing “too relaxed” nor “too formal” might work best. Comfort is also critical in that when we feel comfortable it contributes to feeling confident. Common sense is knowing how to contextualize the different norms and acceptable variables within each job. In other words, target dressing to suit the norms of the industry, and the look and feel of the company: how we dressed when working for an established accounting firm may be different from how we dress when working at a start-up company.

Concrete staples that we might consider purchasing that are in keeping with our budget should include essential and classic basics that can be personalized with varying styled accessories to express individuality (scarves, jewelry, belts, ties, work bag/tote):

For women, opt for a black pants-suit, black skirt, 5 blouses, black heels, and neutral colored heels.

For men, opt for a black or gray suit, a navy or brown suit, 5 solid colored collared shirts, black shoes, and brown shoes.

Buy the best quality you can afford. From there, acquire one or two additional pieces over time until you build what you deem a complete work wardrobe.

When it comes to interview dressing, it’s safe to assume that if you look the part then you have an advantage over others, all other things being equal. Because first impressions can tip things one way or the other, consider a “standard interview uniform” that makes you feel relatively comfortable and confident and that screams “neutral”—one that won’t invite any attention from the interviewer that potentially overshadows you.

That “dressing privilege” and “dress expectation” are alive and well does not mean that what we wear cannot be an extension of our personality. When we feel confident with our appearance, then that confidence is conveyed through our corresponding performance. So go ahead and rock that off-the-rack item, those last season accessories, and that non-branded footwear! Here’s to your dress success!