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Life, Values & Legacy: Our Chat with Zoe Hennessey of Hollywood

We’re looking forward to introducing you to Zoe Hennessey. Check out our conversation below.

Good morning Zoe, it’s such a great way to kick off the day – I think our readers will love hearing your stories, experiences and about how you think about life and work. Let’s jump right in? What do you think is misunderstood about your business? 
I think the biggest misconception about styling and personal shopping is that it is fast and easy – that I walk into one store and find everything in one go! In reality, it is a lengthy, multi-step process. When shopping for a client or a job, I search multiple stores and websites, often spending hours scrolling through countless pages, adjusting filters, and switching between tabs comparing options. In person, it means checking different locations and going from store to store, carrying heavy bags, and being on my feet all day.

Once the pieces are found, there is unboxing, hanging, organizing, and then building looks, which can take hours on its own. After that comes packing for transport, unpacking at the shoot or fitting, repacking and reorganizing, and returning. This does not even touch on the challenges of sizing, availability, or budget.

It is a lot more work than people realize, but ultimately, I find it very creative, fun, and rewarding.

Can you briefly introduce yourself and share what makes you or your brand unique?
I am a fashion stylist and personal shopper. As a stylist, I work with brands to source and style clothing for photo shoots and commercials, collaborating with creative teams to bring a product to life. As a personal shopper, I help clients build wardrobes that reflect who they are or who they want to be, often starting with a closet edit, then shopping and styling new pieces. I love helping people feel more confident in what they wear. It is amazing how much the right clothes can transform how someone feels.

Okay, so here’s a deep one: What’s a moment that really shaped how you see the world?
Once I started practicing guided meditation, I noticed a real shift in how I see the world. I became less overwhelmed, less worried, and more grounded. One of my favorite quotes is “Little things do not matter, and everything is a little thing.” Of course, there are moments in life that are truly impactful, but maintaining that perspective helps me navigate daily life with greater calm and clarity.

Was there ever a time you almost gave up?
Absolutely. I have often thought about securing a full-time position with a salary, health benefits, and stability. The challenge is that I have not found anything that feels like a place I could stay for years. Being a freelancer comes with both sacrifices and rewards, and nothing is perfect. I truly love what I do, but there are times when the idea of a consistent paycheck is very appealing.

So a lot of these questions go deep, but if you are open to it, we’ve got a few more questions that we’d love to get your take on. Is the public version of you the real you?
No, I think I tend to put my best self forward more than my everyday self. I am still not completely comfortable on social media, and posting often still feels a bit stressful. I want my content to reflect my work and my perspective, but it can be challenging to balance authenticity with how I want to be seen.

Before we go, we’d love to hear your thoughts on some longer-run, legacy type questions. If you retired tomorrow, what would your customers miss most?
I am a creative outfit builder, and I think my clients would most miss my ability to put together looks that are both unique and unexpected, yet perfectly suited to them. They often discover combinations they never would have imagined on their own, and that is something I love helping them experience.

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