There are an array of strategies that go into becoming an effective stylist – or so we’ve learned from Cindy Conroy. By attending to the balancing act of coordinating the many different aspects that ensure each project is seamless from beginning to end, and adapting to the needs and personalities of her clients, Cindy has mastered the art of styling individuals from all walks of life.

Some of us are fortunate enough to know our calling before being forced to think about it during crucial decision-making times like applying to schools with our majors or choosing the best city to live in based on our interests. Knowing exactly what it is you want out of a career can take years to figure out, which is normal and fine but for some the decision was easy based on their natural passions growing up.


HOLR: When did you discover that fashion was a big interest for you?

CINDY: I remember at a young age looking for a pair of earrings to wear. After scouring my jewelry box, I finally found a lovely pair of bronzy, dangly earrings. As I put them on I thought to myself, “Do I really have to wear a pair?” I decided the answer was no and went to school that day wearing one dangly
earring and one stud.

“I felt so beautiful and at that moment I knew, I loved the transformative power of fashion!”

HOLR: What was your first job in fashion?

CINDY:My first job in fashion wasn’t actually a job and it wasn’t a fancy gig at a major brand. I must have been 11 or 12 years old when I volunteered at a bazaar to raise funds for underprivileged people. At the time my mom helped organize the event, so I begged her to let me run the clothing and accessories boutique. I desperately wanted to sell the shoes, purses, and jewelry and simply be around all that beauty. And man did I do it! To this day I remember helping others find so many goodies.


HOLR: Why a stylist rather than another job in fashion?

CINDY: I think it’s incredibly important to volunteer, which is why over the course of my life I’ve done a lot of philanthropic work. Someway, somehow, this steered me to styling. Whether I’m doing 1:1 styling,
posting an inspiring message on Instagram or doing a commercial project, my work helps someone feel
attractive, confident and empowered. That’s why I love being a stylist. Each day I help men and women
to further love and embrace who they are – flaws and all!


HOLR: What’s your process for finding out more about a client’s personal tastes and overall goals with styling?

CINDY: I simply listen. A lot of people don’t know how to actively listen to others. Instead they are thinking about how to reply. I truly listen to my clients to learn what their goals are, what they like and why they sought my help. Do they need sexy outfits for upcoming dates? Are they attending an event and don’t know what to wear or don’t have the time to pick something out? Have they gained a few pounds and don’t know how to dress their new shape? Do they want a few outfits for work or play? Are they
recently divorced and looking for a change in wardrobe? Whatever their need or problem, I solve it!


HOLR: What’s the best way to organize a freelance stylist schedule?

CINDY: The key is organization. If you’re a freelance stylist you have to coordinate all aspects of your business – from client interactions to sessions to shopping expeditions. So if you aren’t organized, everything will fall apart. Once you hone that skill a lot of things fall into place.

HOLR: How do you bring out confidence in your clients?

CINDY: I find them exceptional clothes that highlight their attributes and minimize their problem areas. If I get the green light for accessories too, I find them shoes, hats, jewellery, belts (etc) that are flattering,
unique and captivating. After I do that the confidence comes – and sometimes a hair flip or two.

HOLR: What’s some pieces of advice you think would be key for a new stylist to know?


 Always keep abreast of the latest trends.
 Do what feels authentic to you.
 Network, network, network.
 Trust your gut.


Follow Cindy through her journey as a stylist on her social, @iamcindyconroy