Entrepreneur Sponsored Technology Women Who Lead

How Hayley Elsaesser Challenged the Fashion Industry’s Status Quo

Sponsored By Microsoft Surface

At a young age, Hayley Elsaesser’s interests were largely defined by colouring books, paper dolls, and all things pop culture-related. Calling herself a “visual sponge,” Elsaesser explains that her love for fashion stemmed from growing up in the small town of Cambridge, Ontario, where the majority of her clothes were purchased at thrift stores. As she spent years perusing the racks of unorderly clothing featuring eclectic styles and patterns, her eye for design only intensified. Of course, this was years before shopping secondhand was vogue. Back then, her mom would try to steer her away towards something a tad more conventional, but Elsaesser was never one to bow down to the industry’s stylistic constraints.

As she got older, Elsaesser began exhibiting signs of social anxiety. Suddenly, her ability to express herself through clothes became more pertinent than ever. “It got so bad that I couldn’t even talk to people,” she expresses. When she got to university, she recognized that fashion was her calling and not just a passing interest. “I started off studying psychology — I quickly realized I needed to reevaluate my priorities and pursue fashion,” says Elsaesser. 

Having yearned for a way to express herself in ways that words couldn’t, Elsaesser opted for practices like sewing and airbrushing. Her DIY skills came in handy when she began to tackle laser-cut fashion, which is the act of using a laser to meticulously cut and craft materials. From there, she carried her tech background through the fashion realm.

Fuelled by her growing skillset, she then travelled to Australia, where she studied fashion and immersed herself in the profession. In 2014, Elsaesser returned to Toronto and established her eponymous clothing brand, Hayley Elsaesser. At nearly a decade old, the label is widely celebrated as an organic, body-positive brand, working to include diverse bodies in the fashion industry. The brand also encompasses themes of nostalgia from the pop culture staples she’d grown up with, where Elsaesser pays homage to “simpler times” through colourful patterns and designs. 

Many of Elsaesser’s roadblocks came with being a plus-sized woman working in the fashion industry. “[At university], I couldn’t wear my own samples,” she recalls. Body exclusivity has long been one of the main critiques vaulted towards the fashion industry. But in the world of fashion, exclusivity isn’t just something pervading the industry’s design choices, but also its business practices.

“As a woman [in the entrepreneurial space], [I’m] not taken as seriously as I should be,” she says. One of her most visceral experiences, she recounts, was when entering a meeting alongside her brother. He had just started working with the brand, so she brought him along to help integrate him into the business. But despite politely sitting on the sidelines of the meeting, fellow men in the room still looked to him as the label’s authority.

“People would look to him for answers because he’s a man. It was both eye-opening and frustrating.” In ways though, Elsaesser used this to propel her work forward. “When people make assumptions and underestimate you, and you blow them away, it’s even better,” explains Elsaesser. 

Her best advice for young, women entrepreneurs is to “be assertive and have confidence in yourself.” Elsaesser stresses the importance of supporting other women alike, those who are also trying to make their mark in the industry. “Sometimes, you have to fake it before you actually have it. But in those cases, just think of what a guy would do in that situation. Think, ‘What would Chad do?’ and channel that confidence, even if it feels irrational. Because the men at the same table as you aren’t second-guessing themselves, so neither should you. You’re there for a reason.”

RELATED: Svetlana Atcheva is Redefining Excellence at Pearl Morissette 

When COVID-19 hit, Elsaesser got lucky. Her storefront on Queen Street shifted to online-only on March 1, 2020, just in time for the lockdown. Since then, she’s been online but has found keeping motivation while being isolated to be the most challenging part of running the business. “It’s hard to be a creative and push yourself,” she says. But when the creative juices occasionally run dry, Elsaesser relies on technology to keep the business running efficiently.

For Elsaesser, she feels that the use of Microsoft products has helped direct the pace of the label’s business ventures. “I love Microsoft, especially their Surface products, because [they aren’t only] powerful computers, but you can draw on the screen.”

She explains how much of what she does is made up of digital drawings and scans, which is very easy to do as a Microsoft user. “I have all of my prints saved across my devices, I keep everything for years. […] I love the brand because they’re always very supportive of my identity as a creative person,” she explains. 

With the help of high-tech products, Elsaesser can stay confident in her design abilities while seamlessly expanding the brand’s business acumen. With the traction she’s garnered over the past few years, she hopes to challenge other brands, her greatest triumph being her emphasis on body diversity and positivity. Through her array of designs, emphasis on inclusivity, and growing popularity, Elsaesser’s label is creating the vessel for self-expression that she once found amongst the thrift store racks years before.