Q&A: Getting Real With Fashion Stylist Cindy Conroy!

Updated: Apr 29

An Exclusive Interview by Lisa K. Stephenson

While the empowerment of single women is always at the top of our list, we can’t help but recognize and love our sisters who are in healthy, prosperous unions. Our team sat down with Fashion Stylist Cindy Conroy who, as always, was all smiles and we couldn’t help but ask, are you single? Amicably she said, “No, I am very much taken. He’s a great guy that makes me laugh!” As we figured considering that smile. We’re always elated to hear about the wonderful ways in which our sisters are enjoying their unions while still making time for their booming businesses and adoring clientele. Cindy is no different, in this BOLDBoss Q&A we’re getting to know the Canadian Fashion Stylist in the comfort of her own backyard.


BOLDBoss Question (1): What is your ideal romantic getaway?


CC: Oh boy, I don’t think I’ve ever thought about this. Whatever it is, it will have to involve massages, wine, great food and beautiful surroundings. Maybe somewhere like Bali, Amalfi Coast, Nice or Bora Bora. I’ve never been to any of these ultra-romantic locales so being whisked away would be very cool (and he’d get lots of brownie points for organizing it!)


BOLDBoss Question (2): Tell us about your career, how did you get started in fashion and what makes you stand out from other stylists?


CC: If you had told me 10 years ago that I would become a business owner, I’d say “absolutely not”. Yet here I am. I went from being a business exec to an on-air TV Fashion Expert and Stylist. From reading Cosmopolitan to being inside the magazine. Despite a mountain of fear and anxiety, I took the plunge and started my business. I had no formal fashion training. Just a business degree, an eye for style and a lifetime of buying exquisite shoes, stunning clothes and jaw-dropping jewelry. Armed with that, I started a website and my styling business was born.


At every turn there were major roadblocks. Setbacks that made me want to cry a river. I was entering an industry I had no formal training in and the learning curve was steep. I was used to sitting in my cubicle at my 9-to-5 working on reports. Yet I kept knocking on doors and persevering because I truly didn’t want to be 65 years old and think: What if?


At first I thought my meandering path was a hindrance, but over time I’ve realized it’s a strength. It sets me apart from other stylists. My collective experiences allow me to see things differently and thus, style differently.



BOLDBoss Question (3): We've heard many quotes from famous fashion designers such as McQueen, Chanel and Versace to name a few, what are some memorable, unique fashion quotes of your own you'd like to share with us?


CC: 1. Clothing is just clothing, but when harnessed the right way it can change lives! It can give you newfound strength to pursue your wildest dreams.

2. The right head-to-toe look will have you emanating confidence from every pore.


BOLDBoss Question (4): Aside from fashion, what are some of your greatest indulgences?


CC: Food. I love to eat great food. If it makes my mouth water or my taste buds tingle – then I’m all for it. From Asian dishes like Pad Gra Prow to Ackee and Saltfish to Mexican food.

In my experience a lot of my wow meals have come from little “hole in the wall” restaurants. So whatever you do, never dismiss those gems. They’re often filled with delicious treasures that will have you dreaming of food for nights on end.


BOLDBoss Question (5): What is your beauty secret?


CC: I have a couple of beauty secrets that I swear by. First up is good ol’ fashioned sunscreen. As a kid I started using facial sunscreen even though none of my friends were using it. My 10 year old self was determined to protect my skin and prolong wrinkles for as long as possible. I’ve been applying it every morning since.


I also do at-home facials once a month: Exfoliation + Mask. A few years ago I swapped out harsh scrubs for a Clarisonic brush to really deep clean my pores. It gets all of the grimy buggers out and leaves my face feeling super clean. Then I follow up with a mask to detox my pores even more.


BOLDBoss Question (6): Take us down memory lane, can you share with us your most memorable moment in the industry?


CC: I’ve had so many incredible moments that I’m still pinching myself. From my first on-air TV segment to styling my first magazine editorial. Booking my first public speaking gig with an audience of 100+ was a major milestone as well.


Recently I keep thinking about last summer when I modelled for a swimsuit photoshoot. I was coached by supermodel Stacey McKenzie (loved her on America's Next Top Model so big thank you to Ken Mok, Kenya Barris and Tyra Banks). It was truly a fantastic experience to go from being the stylist to being a model. Now I love every minute of being an on-air Fashion Expert and Fashion Stylist, but that shoot sparked something in me. I realized I really like being on the other side. So I’m excited to explore more opportunities that require me to be in front of the camera, rather than behind it.


BOLDBoss Question (7): When we see celebrities take the red carpet and begin reciting the names of their designers, do you sometimes wish the stylists would receive the same recognition? If so, why?


CC: It’s like you read my mind. Yes! I put so much thought into each outfit I craft. I consider the client, trends, silhouette etc. All of it comes together so each look tells a story. Whether my client’s in a magazine editorial, walking down the street, wearing my look on TV or walking a red carpet, a little part of my heart is woven into the ensemble. I’m obsessively inclined to give them the perfect look. So absolutely I think stylists should get highlighted. We work really hard to curate a look that makes our clients feel fabulous and cause onlookers to think: Wow!


BOLDBoss Question (8): How do you look to balance being an entrepreneur and a nurturer at home?


CC: Life is more than just work. It’s about meaningful relationships, family and doing good in the world. I regularly eject myself from work to focus on the other amazing aspects of life.

Home is where the heart is, so I take great care to nurturer it! Maybe I silence my phone for a few hours to spend quality time with family and friends. I might whip up a yummy meal in the kitchen and invite my girlfriends over to gab. Cooking is one of my many love languages, so when time allows, I do it!


BOLDBoss Question (9): How do you handle your most stressful days?


CC: I’m all about “me time”. On my most stressful days I prioritize it. Whether it’s day-of or a few days later, I make sure to carve out time for self-care. Without it I can’t recharge and be the best version of myself.


BOLDBoss Question (10): What is some advice you would offer aspiring fashion stylists?


CC: Just the other day I was onset styling a client for TV. After I had dressed her I walked her to set and waited in the background as the camera crew filmed. In between taping an intern came over and introduced herself to me. We started chatting (because the next few shots had no audio, so we were free to whisper) and she asked me for career advice. So I’ll tell you what I told her:


1. Believe in Yourself: If you don’t, how can you convince others to buy into your dreams?


2. Hone Your Craft: Work hard. Honestly assess your weaknesses and strengths. Pinpoint what you enjoy doing within the realm of your craft and what irks you. Use these revelations as your compass.


3. Follow Your Gut: My instincts are never wrong. Whenever I don’t listen to them, I always pay the price. So trust your gut and follow it. You might not definitively know why your gut is pointing you in a direction but if it feels right, I say go for it.


If you do the above you’ll see great things blossom in your career (and life).

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