I met Annie Thompson on a cold December day in 2013 as I wandered through Chicago’s Merchandise Mart exploring the annual One of a Kind Show. The event is a four-day ordeal (seriously, there’s no other word for it) where thousands upon thousands of square feet are packed with booths featuring artisans from the world over, ready to sell their creations to Chicagoans hungry for bespoke wares.
Annie’s booth was stationed on a corner, her signature, borderline steampunk designs hanging like art begging to be taken on a walkabout. From the moment I stepped in and started touching the fabrics, I knew I was in trouble. The best kind of trouble.
I tried on my first piece, a sleek black and silver three-quarter length vest with a detachable hood. I was home. Annie stood in front of me, adjusting. Dressing me. Bringing me other styles. Showing me how everything she created came together to tell a story.
When you’re trying to build a creative business, it’s easy to feel as if you’re competing against faster and cheaper companies. Thompson offers these ideas to help you build a company that honors your talents and allows you to do business with people you love to serve.
Did you always know you wanted to be a clothing designer?
Actually, no. While I’d always made my own clothes from an early age—as early as grade school—I went to university for fine arts. I imagined traveling the world with a little briefcase filled with pastels. I was always interested in making. While I was studying art at university, I went to check out a fashion design program at Ryerson University’s School of Fashion and I was lost in the most wonderful way. I got lost in the art of building things. It matched perfectly with my love for creating and seeing designs come to life, from 2D to 3D. I have always had one foot in art and one in fashion. I’m an artist of clothing and functionality now. I create clothes that women want to wear because they work and feel great. You feel like the best version of yourself when wearing them and it’s fantastic to help women put that version of themselves out there to the world.
Have you ever wondered whether it’s all worth it—coming up with new collections year after year?
There have been numerous times when I’ve felt like walking away. I rely on so many people to get the product out there, and it gets pretty hectic. There are definitely times where I crave to be only the travelling artist with a little suitcase, an easel and pastels.
What do you think the secret is for not quitting when the going gets rough while running a creative business?
The key is putting your heart and soul into your art all the time. It’s a combination of ball and chain and creative license. For me, there has to be a new collection every six months. There are days I think, “Everything’s been done. And, how do I make something new that means something?” That’s when I start looking at what I’ve already created over the past 30-plus years. I try things on—upside down, inside out, backward. The play is one of many things that I find inspiring. You have to find that process for yourself that shakes your brain and helps you keep creating things that mean something for the people who already love what you do.
You have a single boutique location in Toronto and travel with your collections to shows. Why have you never gone the big box, department store route for your designs?
I know big box is the dream of many creatives, but it’s never quite felt right for me. Going big box would mean I would be much more likely to have to follow the cookie-cutter norm and the schedule that runs the entire fashion industry. I’d more likely be buying fabric that is available to everyone else. I’m never going to do that. I create very limited run collections. I find fabrics where there are a limited number of yards on the roll. That means that once we’ve cut so many pieces, we’ll never make that exact piece again. My customers love that—individuality, exclusivity. And there’s a lot of thought that goes into each particular piece: how the fabric drapes, the finishing details and all the ways a woman will be able to wear it.
Price point is a heavy concern for creative professionals, yet you sell above the department store norm [ranging from $75 for accessories to $1,100 for coats]. What makes you able to command such a high price point?
Part of every garment I make is fit. If you’re going to talk about price, you have to talk about the value you’re giving your customers. This is the other thing that makes big box an absolute no-go for me: I tailor my garments to fit each customer. I want to see the garment on a woman’s body and make any adjustments necessary to make that piece perfectly hers and hers only. That’s value.
I’ve never competed on price and for the longevity, the quality of construction and the inherent uniqueness of each piece, they’re actually quite inexpensive. I source most everything locally and part of my brand is my commitment to a low carbon footprint. That means Canadian-made, organic and up-cycled materials, local fair labor, small production runs and limited edition designs. My customers think I should raise my prices, which says something of the design-appreciating customer base we’ve cultivated.
These women are generally between 35 and 75 years of age. They’re open-minded people and forward thinkers—the people to whom good design matters. They want less quantity and are prepared to pay more. I have discerning customers who challenge me to consistently put something even better out to the world. There’s a difference between putting on something for $39 and $239 and loving how you look and feel in it.That’s what separates the $39 pair of pants and the $239 pair of pants. They’re both pants, yet they both have a vastly different value. It’s a part of my brand I’ll not compromise.
Speaking of setting yourself apart, having a voice is a crucial part of any creative business’ success. When would you say you started to find your voice and forge your own way as a clothing designer?
When I had my first store in Peterborough [Ontario, Canada], that’s where my voice began. I was just out of design school. People were buying my clothes. I was creating, people were buying. When people start buying what you create, it’s awesome creative fuel. You get permission to keep creating. As I mentioned before, it’s important that you put your heart and soul into your art all the time. As I created more, I found what worked, what people liked and wanted more of, and was able to keep building on that. That’s what I’ve done for the past 30 years. I don’t think I’m done finding my voice, because through all that creating, I know what I love creating. There’s a piece of you in everything you make as a creative. Don’t lose that.
What advice would you give to other creative-oriented businesses when it comes to finding their voice in very noisy industries?
I would say you have to jump off the cliff. Jump not knowing. That’s part of being creative, whether you’re in a creative industry or not. You’re going into an abyss every time you pull a new idea out of your hat. You have to be comfortable being in a state of not knowing. I’m not sure any of us are truly comfortable there, but we know we have to be in that uncomfortable place for something amazing to happen.
We get scared to jump because we can’t see what’s ahead. That’s understandable. But think about it like this: If you can picture the first 200 feet in your mind, go ahead and get 50 feet in. Once you get 50 feet in, something else will show up. If you want to know all the answers, it’s going to stop you from taking the jump. It’s risk. Accept it. Start experimenting. And don’t worry about being good. Get into that experimental stage. And don’t try to be cool. Cool can be really boring. You have to have your own style to make a go of things—that applies to anyone in any business. Following trends isn’t going to get you noticed. I decided a long time ago to do my own thing and see what people liked. Then I used what they liked about my own thing to improve on the next thing. It’s all still me and has been for 30-plus years now.
What’s the toughest thing you’ve learned as a creative business professional?
Believing that people will stick with me and want more of what I have to offer.
Marketing has always been a challenge, so I’ve had to find ways to get who I am and what I do out there in a way that’s right for me. Traditional “marketing” doesn’t feel right for me, either. As a creative professional, you have to find the best ways to advertise yourself. That’s what’s going to get the word out and get the point across to new customers. It’s also what’s going to keep your existing customers coming back, that staying top of mind.
My advice if this happens to be your challenge, too? Be your own advertising. Wear your creations. Get out there. Carry cards. Don’t be just in creation mode 24/7. We can get reclusive, but we mustn’t always be reclusive. It’s one thing if I’m in lockdown because I’m creating my next collection, but I can’t stop being out and about. I design clothes for women like me, who want to feel great and look stylish in everything they wear. I feel happily expressed and calmly empowered when I wear my clothes, and I’m my own best advertising, next to my customers.
Finally, what one piece of advice would you give a growing creative business when it comes to standing out instead of “selling out”?
People often think radically new ideas are impractical and won't take flight. Refuse to be held down if you have talent and chutzpah and are willing to work your butt off. Offer something new and fresh. Following is for followers. Be like Sinatra. Do it your way.
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Photos: Getty Images, David Shuken (3)