Meet Aynsley and Christine, Founders of

The FLARE team stopped by The September's launch party before the holidays, where we caught up with founders Aynsley Wintrip Harris and Christine Carlton.

The September's founders at its Toronto launch event // Photo by George Pimentel

The September’s founders at its Toronto launch event // Photo by George Pimentel

How did you two meet?
C: We were roommates in university and have now been friends for 20 years. We had parallel careers working for luxury brands; Aynsley worked for The Four Seasons and I was at Holt Renfrew. Aynsley can elaborate on how The September came from all this.

A: Well, it was over a very casual conversation. I was at home with my kids, working and always busy which ultimately led to an influx in shopping online. If I couldn’t find what I was looking for, I reached out to Christine and said, “Why isn’t anyone in Canada doing online retail?” Then it clicked! We thought: Why not give it a try? We had the right experience, working for these two great luxury brands, and the more we looked into it, the more we thought it was meant to be. Not once did we look at each other and think, Are we crazy? We just went for it. Everything pointed us in the right direction.

How does you go about beginning an online shoe retailer?
C: Where do we begin … How many hours do you have?

We’ll make it easier. What has been your biggest hurdle?
C: We sat down and put together a business plan; like all good entrepreneurs, we had a plan (and investors). Each part of the business presents different challenges and you find ways to work through them. There are so many aspects to a business, and since we’re rooted in technology we spent a lot of time finding the right partners for our business. It’s a philosophy from The Four Seasons, that who you work with is so important to what you do. We spent a lot of time researching the developer, Canadian Consumer Laws, meeting with designer brands and finding the expertise required to successfully launch an e-commerce platform. What was most tricky was deciding which brands would resonate with all Canadians and not just ourselves. We felt it was really important to introduce new brands that offered spectacularly designed product paired with the exceptional quality that we knew our customers would expect.

How did you find the right brands?
C: Mainly from being in the industry. When you go to market for buying and interacting with the vendor community, it’s a very open dialogue. They don’t necessarily see other brands as competition and they do support emerging designers. In some instances emerging designers are recommended to us from one of our existing brand partners, and in others we discover them by reading trade papers, going to the runway presentations and by visiting showrooms. There is so much footwear news, you have to just read all the information.

A: And we have some friends in the industry! An interesting designer is Paul Andrew. I know you’ve written about Paul Andrew in FLARE and as Christine said, he was referred to us by another vendor who said we had to check out the showroom. We were in New York and decided to pop in. Upon arriving we instantly fell in love and knew immediately it was something that would appeal to our customers. Beautifully made shoes, beautiful materials.

Do you have plans to sell men’s?
C: We’ve been asked that a few times, actually! You never know. It also is an opportunity. The mens footwear business is rapidly growing so we don’t know. There’s no rules at this point. That’s the nice thing about being entrepeneurs, we decide what the future is and [work] with what our customers want. Part of what we wanted to do was start in one category and then grow based on consumer feedback. What does the customer want? Which brands? Which styles? Do we want mens? What about bags? Do the customers want handbags? Who knows where we will end up. We are so excited about being a homegrown option for Canadians.

How many labels do you have so far?
C: We launched with six and have another five or six coming for spring 2014. Every season we are going to layer in a new brand. As you know, in fashion, there are so many collections: Spring, Summer, Resort, Pre-fall, Fall—it never ends. So with deliveries constantly coming, we will have new product added to the site almost every week.

Will there be sales?
C: Yes. With retail there are sales. We will follow the same sale schedule as most Canadian retailers. At the end of the season, things will go on sale.

Being a new business, what advice would you give to any aspiring online retailers?
C: That’s a good question. I think it is a very small community, it’s in its infancy. We need more players. We absolutely do. There is a void in Canada. The vendor community we work with call it a black-out. And it’s true: There is an e-commerce black-out in Canada. We wanted to change that and, you know what? We would encourage anyone to absolutely go for it. There are so many different levels of the market and there’s plenty of room for everyone. We are big believers in competition so we hope others hop on board.

So if you could each choose one style that is available on The September what would it be?

Together: Other than what we are wearing? [Studded Valentino pumps]

C: I love the Gold Aquazzura Beverly Hills. That’s my next pick.

A: The Paul Andrew Calliope sandal, with Swarovski crystals over the toe. It’s spectacular, and certainly my favourite at this time—though my favourites are forever changing.

C: And that’s something that was inspiration to us. Everything on the site is something we love ourselves. That’s how we approached curating

Free shipping, free returns and no duties – awesome.

Editor-in-chief Miranda Purves at The September's Launch Event

Editor-in-chief Miranda Purves at The September’s Launch Event


Fashion director Tiyana Grulovic and senior style & market editor Truc Nguyen at The September's Launch Event

Fashion director Tiyana Grulovic and senior style & market editor Truc Nguyen at The September’s Launch Event


Assistant fashion news editor Emily Ramshaw, Chatelaine's Tyler Franch and assistant market editor Jillian Vieira at The September's Launch Event.

Assistant fashion news editor Emily Ramshaw, Chatelaine‘s Tyler Franch and assistant market editor Jillian Vieira at The September’s Launch Event.


Digital editor Andrew Lovesey (me!) at The September's Launch Event

Digital editor Andrew Lovesey (me!) at The September’s Launch Event