“You look like a humanoid from the Elder Scrolls”

“Is it my leather headband?”

“And the thigh-high boots with those dangly things”

I’m in a stretch crop top with oversized, protruding pagoda shoulders. I paired it with a double-layer tank that can be worn off one shoulder, the second shoulder strap peeking out below a wide stretch viscose cummerbund. My big leather pants are almost completely engulfing my razor-sole combat boots; just the tip of the toe peeking out from the hem. I’m ready for a day of work at my tech job. Glance around the office or Zoom room and something is painfully clear:  Amongst a sea of collared shirts, peplum blouses and logo tees, I stand out.

Does the average professional really want to show up in a suit and tie or the jeans-and-tshirt tech uniform? Maybe they do, but I suspect others feel the self expression they crave would place unnecessary hurdles in their climb up the corporate ladder. They save it for the weekend, or simply deny themselves. For those on the fence, I want to offer a bit of hope: standing out can actually help you build your career.

I was raised in Sault Ste. Marie Ontario, a twin city on the Michigan border with a population that has steadily decreased since the early 90’s. Young people leave for greener, more exciting pastures and the local steel industry’s decline sends families to places where jobs are more abundant. I recall asking my mother if I could wear her short black persian lamb and tan mink collared coat to school several times when I was 5. Each ask was firmly denied. Sure, she didn’t want to see it destroyed in a kindergarten classroom, but she also knew I’d be teased in a place like The Sault. I can understand my mother’s intent to protect me, but I was determined to be myself.

But the remarks became more pointed as I approached high school. It felt bizarre to face hostility just for looking different, and for a few regrettable years I did my best to try and fit in. At the time, fitting in meant wearing bootcut American Eagle jeans and Guess logo tees, but I still couldn’t help adding an unexpected accessory here and there. Then, one summer, I discovered MySpace. High on connecting with others who shared my passion for fashion (and my confidence buoyed from a few hundred “fans” who loved my penchant for fur and drawn-on eyebrows) I arrived back at school with a renewed drive to give the world my absolute true form. The world could take it or leave it, and I never looked back.

When I branched out to the big city, my career started in fashion retail, where self expression was encouraged. The fashion world is full of people trying to stand out. Still, styling requirements for retail workers usually encouraged gender stereotypes like heels for women and collared shirts for men. Skirting the rules was always accepted as long as I presented myself as stylish, confident and ready to sell.

Seeking something new, I made the switch to tech after losing my job to restructuring. Part of the attraction? There was no formal dress code. The CEO wore board shorts to board meetings and employees often converged at the office in sweats, Birkenstocks, athleisure, and even pajamas. Tenured employees were recognized through the age of the swag they wore, and my employer produced lots of it. For many, this provided a sense of comfort that they fit in with their colleagues, and a feeling of thanks that they didn’t have to worry much about getting dressed in the morning. My own company swag ended up as gifts to my partner, friends and family members; I proudly wore whatever I wanted.  

The author on his commute to his job in tech.

At the office.

People often ask if my outfits lead to being taken less seriously at work. On the contrary, I’ve found that dressing unconventionally at the office can be a conversation starter; an eye-catching invitation to engage. I have outfits to thank for several meaningful relationships I’ve built professionally. One year, I was invited to host the company’s biggest annual investor meeting. I did so in 6-inch platform heels. 

“I love those shoes. Look at his shoes!” 

The reaction from the male executives in the room left me no doubt they’d wear the same ones in a heartbeat– that is, if they weren’t so deeply entrenched in conservative and gendered fashion codes. One executive, more likely to be found in the polo shirt section, first started a conversation with me over one of my baggy Rick Owens jumpsuits– he’s now a close career mentor.

I can remember several company events where I was featured as a host, MC or presenter and what I wore to each of them. The holiday party where I delivered an opening bit in my Crocodile Dundee style hat; the networking event where I warmed up the crowd in a plunging leather v-neck; the companywide presentations I gave in everything from layered mesh tanks to a cropped stretch lambskin jacket. While my friends and family marveled at what I was willing to wear to work, I only got positive feedback at the office. It had a snowball effect, giving me the confidence to keep putting myself out there, especially since I had a solid reputation for delivering quality work. I wasn’t just the guy who led a successful project or meeting; I was the guy who did it in heels.

The author at work in his favourite boots.

The majority of us spend most of our adult lives at work. For many, the idea that conforming into a homogenous ball of business casual is one that can be attributed to smooth-sailing career success; that one should only stand out for their work , and then you’ll be promoted in due time. I encourage a different viewpoint: If you’re a little weird, let it work for you. 

If you’re early in your career, consider what it looks like to bring your true self to work. Think about how you’d like to stand out, aesthetically and beyond. Consider how you’d ultimately like to be perceived by your colleagues. Set goals that represent milestones to getting there (e.g., reach out to at least two colleagues to tell them you appreciate them, try wearing that one weird sweater) and pay attention to feedback. Allow positive cues to propel you forward in building a personal brand that sets you apart from the rest. It doesn’t have to be wild or designer; it just has to be you.

If you’re a people leader, all the better; set an example, and you’ll free others to be authentically themselves as well. But even if you’re a jeans and t-shirt type, you also have the responsibility to encourage creativity. Show support for your team members to bring their true selves to work and have (appropriate!) conversations about it. My style and journey is my own, but others, depending on their identities and experiences, might not feel as safe expressing themselves so openly at work. If you value creating that safe environment, let that show in your policies, processes, and hiring practices. You’ll be attractive to talent who are looking for a safe place to stand out, and encouraging to others who are still breaking out of their shell. 

After all, for every tech worker excited to show off a colorfully-printed sock peeking out between their brogues and cuffed chinos, there are many others who yearn to take it a step further. With everyone’s unique self unleashed and accepted, a team’s culture and creativity can truly thrive.