Christine Carlton

Toronto, Ontario

To celebrate our second anniversary, we’re going straight to the top. Here, The September CEO shares her views on women in business, two fabulous years of shoe shopping and what’s next…


TSWhy did you start The September?

CC - I LOVE shoes! I wanted to provide access to stunning luxury shoes to women all across Canada and to transform how they shop! Plus, every great business solves a problem and The September allows Canadians to shop online from a Canadian business without incurring the extra charges you’d experience on an international website. With us, there are no border or custom delays, no duty to pay and no exchange rates to worry about. I was also excited about offering unique one-of-a-kind assortments from brands that customers know and love, as well as introducing emerging and talented new designers.

TSDid you always plan on becoming the CEO of your own company?

CC - I’d refer to myself as an “accidental entrepreneur.” I had a great job working at Holt Renfrew for almost two decades, most recently as VP of Accessories, which included women’s footwear, handbags, jewellery and soft accessories. But I was ready for a change and I wanted to make a difference in the Canadian retail landscape. E-commerce is a rapidly growing sector in Canada and I knew I wanted to be at the forefront.

TSWhat business challenges have you faced that men may not have?

CC - Primarily raising funding for the business. It’s not easy to pitch a business that’s exclusively targeted to women to a male audience. As a result, I shifted focus and targeted female investors and my first group of investors was all female. That’s no longer the case, but according to, an incredible company founded by Vicki Saunders, “only 4% of venture capital goes to female entrepreneurs.” It’s clear there’s still a long way to go to shift this paradigm.

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TSThe September is unique. Why?

CC - I travel the world and personally hand-pick everything for The September, ensuring there’s something for everyone, from fabulous over-the-top high heels to urban sneakers. We actively engage with our customers and react to their wants and needs. I’m not sure if Valentino is a need, but it is definitely a want on The September! We also gift wrap every purchase in our custom-made paper and signature ribbon. Each order is sent out with a hand-written thank-you note because we truly appreciate each customer and, honestly, who doesn’t love to open up a beautifully wrapped package?

TSWhy the name “The September?”

CC - September is a subtle nod to the fashion industry; it really is our New Year. It’s a new season, it’s when all the fashion shows take place around the world and, of course, the September issues of every fashion magazine are the largest and most anticipated. I also have a personal soft spot for the month of September as I was married in September and my first child was born in September. Plus, I think Canada is even more beautiful at this transitional time of the year.

TSHow do you motivate your team?

CC - I ensure we’re constantly discussing and planning “what’s next,” and that I’m hearing ideas from every team member. I do that as much to keep the team excited and engaged as I do for our customers. I also believe in respecting personal time – especially in a field that’s interwoven with technology. Everyone needs to disconnect and refresh by enjoying uninterrupted time away from their desks. And, of course, a good laugh a few times a day always helps.


TSWhat other CEOs do you admire?

CC - Isadore Sharpe, Founder and Chairman, Four Seasons Hotels and Resorts. He built a great Canadian luxury brand based on a simple principle: “It’s the Golden Rule – the simple idea that if you treat people well, the way you would like to be treated, they will do the same.”At The September, we’ve adopted the same principle to ensure that every customer and every business partner has an exceptional experience. As one would expect, I admire Net-A-Porter Founder Natalie Massanet. She truly was a trailblazer.

TSWhat are your two biggest accomplishments?

CC - My role as a mother. Family is everything and I’m so proud of my two children. I well up with pride when I watch my kids doing even the most mundane things. I’m also proud of building a business from concept to reality. I’ve heard so many times that it’s an accomplishment just to get to the launch stage, and here we are celebrating our second anniversary.

TSWhat’s the one word that describes you best?

CC - Perservering.

TSWhat would you tell all aspiring entrepreneurs?

CC - Start with a very detailed plan and execute it flawlessly. And keep in mind you need to be willing to adapt as your business progresses. I meet many aspiring entrepreneurs and they usually have a great concept, but have yet to put pen to paper. It’s so important to flush out your ideas and all aspects of the business, from marketing to finances to human resources and service.

TSWhat’s your favourite part of the job?

CC - Hearing from happy customers. There’s nothing more rewarding than when customers take the time to share their shopping experience. One customer has loved shopping with The September so much she called me to ask for our Pantone colours, as she wanted to decorate her Caribbean vacation home in our navy and cream! That was a fantastic call to receive.

TSWhat’s a typical day at the office like?

CC - There’s no such thing! Our team is dynamic and growing, so there are constantly multiple projects happening. In the span of a week I could be on a buying trip, at a photo-shoot, on the phone with customers, meeting with investors – anywhere really!.

TSDescribe The September customer.

CC - She is sophisticated, well-travelled, effortlessly chic, on-the-go and intelligent. And she adores shoes! She would agree with us that her love of shoes is unlike any other!


TSTell us about your passion for horses.

CC - I grew up around the racetrack. My family is very involved with the horse-racing industry and it’s been in my blood since childhood. On weekends as a child, I would go off to the “backstretch” at Woodbine racetrack with my dad to look at the horses that were racing that day. I love every minute of being around the horses; they are truly one of the most beautiful and graceful creatures.

TSIs there a dress code for the races?

CC - It depends. In the grandstands there is no dress code – it’s a casual fun day at the races. In the turf club, it can be quite formal. My favourite is Queen’s Plate Day, when women dress in finery with fabulous hats and gentlemen wear top coats and tails. It’s like stepping back in time!

TSDo you reassess your shoe wardrobe every fall?

CC - Absolutely! I actually start my fall shopping by selecting shoes and boots that I’ve been coveting. I’ve always done my shopping by starting from the ground up. I find it so much easier to find fabulous clothes to go with my new shoes and boots. I’ve always shopped this way, even before I was involved in the shoe business. This fall I am stocking up on Acne boots and Aquazurra Sexy Things – they are selling like hotcakes.

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TSWhat's on your fall reading list?

CC - I usually have two books on the go, one for business and one for pleasure. I’m currently reading “The Hard Things About Hard Things – Building A Business When There Are No Easy Answers” by Ben Horowitz. He’s one of Silicon Valley’s most respected and experienced entrepreneurs and offers advice on building and running a startup, practical wisdom for managing the toughest problems business school doesn’t cover. I’m also reading The Luminaries by Eleanor Catton. And it wouldn’t be September if I wasn’t devouring every fashion magazine’s September issue!

TSHow do you ensure work does not creep into your family time?

CC - It's not easy, but I remind myself that work creeps into my home life just as much as my home life creeps into my work! At home, we have "technology free" time, every morning before the family heads off to work/school. There's no technology, and that includes wifi, tv, iPads, laptops, iPhones. Also at night, after 8pm, no technology.

TSWhat is the shoe equivalent of the little black dress?

CC - Flat black ankle boots! I have more pairs than I should. For me they’re the go-to as you can wear them with jeans, dress them up for work and they’re also fabulous for a night out! I really love the new ones from Vince.

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TSWhat’s your ideal way to unwind?

CC - Whenever I have the time, I practice yoga at a local studio. I like that it’s in my neighbourhood and gets me out of the house. I’ve been a yoga fanatic for years and even practice it at home in the garden. I was drawn to it because it’s a great stress reliever and beneficial in so many ways. Plus, it’s hard not to feel great after an intense yoga session.

TSWhat music do you listen to when relaxing?

CC - Motown! It’s relaxing and inspiring all at once

TSHow else do you relax and unwind?

CC - With my dog, Mohawk – I love being with him. He’s a golden retriever and he goes everywhere with me. He loves coming to The September offices. He is our CHO: Chief Happiness Officer!


TSYou've worked in the fashion industry for most of your life -- what's that been like?

CC - It’s been a dream job. Who wouldn’t want to travel to Paris, New York, London and Milan for work? The best part is the fashion shows. Every season, when the lights go down and the music starts thumping, I’m reminded of what drew me to the fashion industry. It’s been fascinating to see the introduction of live streaming, Instagram, Twitter and snap chat at the shows. The shows are no longer exclusive, rather globally inclusive – that’s a change for the better.

TSTop "OMG" fashion moments?

CC - Every Stella McCartney fashion show! Each season, if Paul McCartney is at the show, it always ends with a Beatles song. It gives me chills every time I see Paul McCartney sitting across the runway from me, and to see him as dad supporting his daughter! The other has to be meeting the late Oscar de la Renta. He was so elegant and debonair and I was able to chat with him prior to one of his runway shows. He was calm and engaging, a true gentleman.

TSIf you could only wear one designer, who would it be?

CC - Celine. I like pared-down simplicity that's feminine.

TSCosmetic item you can't live without?

CC - YSL Touche Eclat.


TSWhich designer has the most incredible showroom?

CC - Definitely Dior in Paris. It’s located on the Avenue Montaigne, and is the original House where the first store was located and where Christian Dior designed. It’s like stepping back in time with its soft grey paint, grey carpeting and white panelling. The vintage black-and-white photographs of models wearing Dior gowns in the ’50s are spectacular.

TSHas your exposure to showrooms influenced your design aesthetic?

CC - I’ve been in so many showrooms over the course of my career that I’ve selected the best from each and incorporated them into the design of my home. My metallic natural linen family room drapes are inspired by Kate Spade, and the cushions on the sofa are Etro and Missoni: two of my favourite brands for their use of colour. The white Thasos marble in my bathroom is also found in the Valentino showroom in New York. The fabric on my family room chairs was inspired by Kelly Wearstler’s sophisticated use of vintage fabrics. Once, I even snapped shots of door pulls when I was in the Versace showroom in Milan so I could show my designer! On my to-do list now is to add black and white marble tiles to our foyer à la Aquazzura’s new flagship in Florence. So yes, I guess you could say they’ve influenced me!

TSHow would you describe your home?

CC - My home is welcoming and relaxed. When I set out to design it, the spaces were much more formal and sophisticated. As the project progressed, I realized we were gravitating to more casual finishes and furniture. It became apparent that we needed a space that was comfortable and practical for a busy family. We do however have a very formal dining room, as we have a large extended family and the dining room table expands to 12 feet so we can accommodate 14 around the table – a must at our annual family birthdays.

TSFavourite room and why?

CC - My kitchen. It’s white and bright and opens into the family room, breakfast nook, mud room and dining room. It truly is the centre of our house so when we’re cooking, everyone else is within close proximity. My husband and I are both tall, so we broke with convention and had the counter tops raised a few inches from standard height. Personalization is the key to good design.

TSDescribe your perfect weekend.

CC - Escaping to our year-round cottage in Thornbury, Ontario. It’s located on Georgian Bay and was designed with two-storey high floor-to-ceiling windows. The views of the Bay are endless. It’s my favourite place to leave behind the bustle of the city, as there’s no phone, no wifi and no TV. When summer water sports come to an end and fall sets in, we play cards, board games, read and enjoy time by the fire.

TSHow would you describe your cottage?

CC - Coastal casual.

TSDo you have any fall family traditions?

CC - Thornbury is the heart of apple country – we are surrounded by apple orchards. We always participate in the Apple Pie Trail in Grey County. Our favourite traditions are apple-picking on Thanksgiving weekend and shopping at the local markets. Goldsmith’s Orchard has locally grown produce and sells the best pie in the province – seriously it is worth the drive there! We also frequent the Thornbury Bakery, which has been around longer than I have. Don’t even try to resist their world-famous Chelsea buns!

TSOther than shoes, what are you coveting this fall?

CC - Mud Australia dishes! They’re crafted from porcelain and perfectly meld minimal design with everyday practicality. I love the smooth shapes, clean silhouettes and the truly gorgeous colours – even their shade of white has incredible depth.

TSHow do you describe luxury?

CC - Luxury today is about service and experience, not products. It’s about being in the know, having good taste and not about how much you pay for things.


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