It wasn't long ago that TV Personality and Fashion Stylist, Cindy Conroy, was working your average 9-5 job at a corporate office. Utterly unfulfilled and battling a yearning for fashion, Cindy made a powerful shift towards a career in styling, TV & film and public speaking. It steered her life in a completely different path.
Today, since embarking on her journey as a freelance stylist, Cindy has given life to a successful styling business that has garnered the attention of many, including Cosmopolitan, Medium, eTalk, ET Canada and more. In addition, as a successful entrepreneur and Canadian fashion icon, she's positioned herself at the forefront of fashion in Canada while continuously using her platform to promote messages of positivity, inclusivity and empowerment.
In this interview, we sat down exclusively with Cindy Conroy to talk about fashion, lifestyle and tips on making it in the industry.
Tell us a little bit about your journey. How did you jump start your career in fashion?
I started my fashion career in an unconventional way. Unlike most, I didn’t intern at Elle, InStyle, FASHION or Harper's Bazaar. As a young girl, I reworked the clothes my mom bought me. I was scrounging together my allowance to buy accessories at Claire’s. In university I learned accounting practices like FIFO (first-in, first-out) and LIFO (last in, first out). I would dream of buying gorgeous clothes and jewellery. Alas, I couldn’t afford it. So instead I created “moments” with the wardrobe I had. I would cut my clothes to change the silhouette or wear midi skirts as dresses. The whole time I wished with every fibre that I could convert my “eye” for style into a job. I couldn’t – at least that’s what I thought. As a teenager, no one told me that jobs existed in fashion. I was always taught my career options were to go into business, be a doctor or a lawyer. So I chose business and worked my way up the corporate ladder.
"As a teenager, no one told me that jobs existed in fashion. I was always taught my career options were to go into business, be a doctor or a lawyer."
It worked until one day I realized I didn’t want that life. I was successful in my corporate career, but I wanted something different. This wasn’t me. Shortly after the idea to start my styling business emerged, I started building. Step by step I was determined to be a fashion stylist. Then all of a sudden I was on TV as an on-air Fashion Expert (pinch me) and chatting about self-love and style to audiences of 100+. The rest is history.
Having your own business, what would you say is a normal workday for you?
Every day is different. When I started styling I didn’t know what to expect. I didn’t have a sense of what my routine might look like. Slowly I realized that because I’m an entrepreneur I automatically have to juggle many things simultaneously. So even if I’m prepping to go on-air for a television segment with eTalk, I still have to email back and forth with 1:1 personal styling clients. I still have to handle non-sexy (but very important) accounting and admin tasks or advance conversations and bookings for my public speaking gigs. Then the next day is completely different! I might be on-set for half of the day styling a client for TV then running off to a personal styling session with a mom whose body has changed post kid(s). The next day I might be styling a bride and her bridal party while fully immersed in prep for a magazine editorial or photoshoot. It can be chaotic at times but ultimately very rewarding!
What is the process for creating a look? Where do you draw your fashion inspiration?
I don’t have a formal process, but my ideas often percolate as I listen to great music. I listen to everything. Sometimes I’ll put on an inspirational song (Kelly Clarkson’s Invincible gives me a lot of strength) or play something timeless from an artist like the Queen of Disco, Donna Summer. Or if I’m out and about something might catch my eye, triggering my creative juices. It might be breathtaking interior design, floral arrangements or the storyline of a great movie. In addition, an idea might pop into my mind right before bed. As I try to fall asleep, the things I’ve done and seen that day inspire me. Magically the vision for the look
starts to form.
What are some staple pieces everyone should have in their wardrobe? Feel free to name more than one!
Wardrobe essentials are incredibly important. I’m of the mindset that you don’t have to own a lot of clothes and accessories but you do need to have full breadth in your wardrobe. That’s why I help people curate a balance between quality essentials and trendy pieces – without being fixated on quantity.
Countless times I hear people say: I need a new outfit for work, a wedding or a night out. Instead of frantically heading to the mall and picking up something that’s “ok” (and often subpar), I recommend building a wardrobe in prep for all of life’s needs. Have the perfect dress, suit and a mix of tops and pants/skirts that you can interchange to create dynamic outfits. Build out your shoe collection by starting with classics and neutrals. That way, when you get dressed your footwear enhances your outfit, rather than distracts. Have hats, ties and purses that are quality made and exciting. If you do all of this, you’ll be stress-free the next time someone invites you out or your boss asks you to attend an important meeting.
"I recommend building a wardrobe in prep for all of life’s needs. Have the perfect dress, suit and a mix of tops and pants/skirts that you can interchange to create dynamic outfits."
What are some designers or brands that you think highly of in terms of fashion, or that you've often thought of as muses, why?
Alexander McQueen inspires me on so many levels. The beauty. The pain. The style. It’s a beautiful whirlwind.
What movements and achievements in the fashion and media industries are you most proud of?
I’m so happy that diversity is being embraced. From highlighting different body types, physical mobility to ethnicities. The fashion world and media are opening up to become more inclusive. They’re creating a breeding ground for love and acceptance. That’s amazing!
What would you like to see change in the fashion or media industries?
I’d love to see clothing recycling programs popping up everywhere. Just imagine if major retailers embraced this initiative – and as an incentive offered people discounts towards their next purchase. It would give you a convenient way to donate select (and great) wardrobe pieces that in return others could enjoy. Someone else’s “pre-loved trash” could become another’s treasure. Garments like trousers, skirts and tops (that you wear regularly, infrequently or never) could quickly spice up someone else’s closet. Any tired clothing on its last leg; those textiles could be recycled for other business purposes.
Making an incremental shift like this could truly change the fashion industry for the better!
What personal impact do you want to make in the fashion industry?
I really strive to make a difference in fashion. To move the needle on how people define the industry. As part of that, I want to create a safe place for people – whether they’re a model, designer, fashionista, MUA (Make-Up Artist), stylist, fashion novice etc. A place where everyone can feel supported and welcomed. Where we build each other up, rather than compete and tear each other down. There’s space for all of us and the mentality should be: I’m awesome and so are you. How can we collaborate? How can we help each other? How can I support and welcome you into the fold?
What is your style philosophy?
My style philosophy is simple:
If it’s not fabulous, I’m not wearing it! You can and should wear outfits multiple times. Don’t forget rule #1!
Any last words of advice for those looking for a career in fashion and media?
Have a dreamy plan. Envision yourself in your ideal role. What does it look like? How does it make you feel? Who are you working with? Now hold onto that and start brainstorming how you’ll get there. Then put the work in.