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Petite Bourgeoisie: Jillian Wood, Owner of Headmistress
What it really takes to run a successful fashion accessories company

All images by Kalen Hayman

A new series by Carolyn Grisold that profiles female entrepreneurs in Toronto

Business Name: Headmistress
Owner: Jillian Wood, 26
Established: 2008
Type of establishment: Fashion Accessories
Neighbourhood: Queen West
Available for sale at: Charlie (809 Queen Street West), Coal Miner’s Daughter (587 Markham Street), Distill Gallery (24 Tank House Lane #103), Frock (97 Roncesvalles Avenue), and at Headmistress’ Queen West studio by appointment
Email: jillian@loveheadmistress.com
Website: www.loveheadmistress.com
Twitter: @Headmistress
Facebook: Facebook.com/headmistressaccessories
Instagram: loveheadmistress

When did you start the business?

Headmistress was born in December 2008 when I made my very first feather headband on a whim one evening. The business really took off when I moved to London, UK, about a month later and started selling at a market there.

Where did the name come from?

The name Headmistress was my mom’s idea. Very early on, we were sitting around the kitchen table brainstorming name ideas and when she said it, I knew it was the one. It’s short, memorable and kind of “punny.” Although sometimes people mistake what the company does for porn, rather than accessories!

Other than in the shops that carry your brand, where else has Headmistress been featured?

Several national publications, like The Globe and Mail, The National Post, FASHION, Flare, Loulou Magazine, Elle Canada, as well as blogTO, The Grid, NOW, and MTVFora.

Do you use marketing consultants?

I’m lucky to have a few friends who work in marketing and advertising who help come up with new and fresh ways to market Headmistress. For example, when the second season of Girls started in January, a friend of mine suggested that we pair up Headmistress products to suit each character, and release one a day for the four days leading up to the premiere. It was a really fun promotion and it stirred up a lot of engagement with our fans via Facebook, Instagram, and Twitter. It gave us a platform to talk about two things that we love — accessories and Girls — in a way that wasn’t only about pushing sales, but also about starting a conversation as well. It’s important to be constantly thinking of new and different ideas that get Headmistress out there.

Did you work in the fashion industry before starting the company?

I had never worked in fashion or even retail before Headmistress. Other than summer serving and hospitality jobs, I have only had one “real” full-time job: after I finished university, I worked for a background checking company and was responsible for taking references about prospective employees over the phone. It lasted for three months.

Did you always want to be an entrepreneur or was it a choice?

It wasn’t really a calling or a choice. It just sort of happened, which isn’t to say that I don’t work insanely hard at it. Suddenly I found myself making things that people actually wanted to buy, without meaning to. My parents are farmers — which means they are entrepreneurs through and through — so I suppose it runs in the family.

Do you have business partners?

No, but I do have lots of help from my family.

How do you feel about the work-life balance question?

[It] gets much more complicated for women when children are involved. One term that makes me cringe a bit is “mompreneur.” I’m not a mother, but if I was, I think I would find it slightly offensive to be called [that]. The term feels like there’s a need to qualify their success and it dismisses women’s actual business skills. I may feel differently if I had children, but I’m just not so sure about that term.

How do you maintain balance in your terms?

There isn’t much of a balance. My work and life are completely intertwined, so work is never turned off completely.

Describe what you mean by “never turning off.”

I don’t think it is really possible to fully separate work and life as an entrepreneur because being an entrepreneur is a lifestyle. As with any lifestyle, there are pros and cons. Some of the pros are that I can take a nap in the middle of the day, or go visit family in the middle of the week without asking anyone. The cons are that the work is never done and there is no escaping it, ever. You get used to this though and I honestly can’t imagine life any other way.

Why did you choose Queen West for your studio?

This was an obvious choice because when I run out of thread, or fabric, or beads, I can go buy what I need in my slippers and be back in less than three minutes.

How has the neighbourhood evolved since you’ve been there?

[My common-law boyfriend and I] have lived in this neighbourhood for about 3.5 years and Queen West has changed a lot. West of Spadina is starting to look a lot like east of Spadina, and it totally freaks me out. I worry about how our small independent retailers will be able to continue to compete with the giant ones that are constantly moving in. This directly affects me since I sell my pieces to many of these small independent retailers that are being threatened by the big guys. I’m crossing my fingers that my landlord doesn’t raise my rent, but for the moment I think I am okay.

How has your business kept up with these changes?

The battle for independent designers and retailers versus huge fast-fashion corporations is always going to be uphill. I think it is important to constantly be educating people in a non-preachy, non-guilt-inducing way about what it means when you buy a product that is made in Canada over a product that is made off-shore. When we buy Canadian, we are supporting each other, supporting better working conditions, living wages and often a higher quality product that will last longer, have a superior fit and better functionality. The tide is turning and more and more people are recognizing the benefits of buying Canadian-made fashion, much like more and more people are becoming aware of and concerned with where their food comes from. All of these issues are linked.

What other kind of challenges did you face when you first started the business?

After growing up outside of Stratford, ON, I lived in Montreal while I attended McGill and then went to London [England], so when we moved to Queen West in November 2009 [to run the business in Toronto], I hadn’t actually ever lived here. A big challenge was getting out there, meeting people and connecting with retailers in the city. I had to introduce people to Headmistress for the first time.

Is that still an issue for you?

People are getting more and more familiar with Headmistress all of the time through seeing my pieces at my retailers, the press we’ve had, my social media outreach and through various shows that I do throughout the year — like the One of a Kind Show and my own pop-up shops. However, the challenge of getting Headmistress out there persists and will probably always be something that I work on.

What do you wish you knew at the beginning?

I wish I’d known how obsessed I would be with my business. I don’t think knowing how all-consuming having my own business would be from the outset would actually have any impact on my choices, but it would have been good information to have before jumping in head first.

What have you learned that’s been the most surprising?

The most surprising thing that has come out of running Headmistress is that I have a bunch of skills and abilities that I didn’t know I had. As a small business owner, I do everything — I’m the designer, sales agent, manufacturer, publicist, marketer — everything. I really didn’t know I had all of this in me.

What do you love most about being an entrepreneur?

I love the idea that I am building something from nothing. There is something very romantic and powerful about that notion.

Could you imagine being anything else? Do you even want to be?

Sometimes I think about what it would be like to have a 9-5 job, and the benefits that come with that. But I can’t even fathom what that job or position would actually be. In terms of an adult job, Headmistress is all I’ve ever really known and there are so many avenues and ideas that I want to explore [within the company], I can’t imagine doing or being anything else.

Is there an area of new growth that you’ve recently implemented or are planning to in the near future?

I recently hosted a solo pop-up shop at The Norman Felix Gallery on Queen West this December — it was a huge success and so much fun. I will definitely be hosting a spring pop-up again and hope to do these regularly. I am also planning on introducing open-studio Fridays where my studio showroom is open for the public to come and see firsthand where every Headmistress piece is crafted. I think it would be a great way to connect with my customers.


Carolyn Grisold is the managing editor of Women of Influence Magazine and a contributing writer to various print and online publications (Post City Magazines, Toronto.com, Gallery Magazine, Argyle Magazine). Follow Carolyn on Twitter @CityandCharm. To suggest a female entrepreneur, please email petty@inningsgate.com

For more, follow us on Twitter at @torontostandard, and subscribe to our newsletter.

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