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The Trailblazer Times: Holly Hollingsworth Phillips

Colorful, eclectic, and layered: these are the three words that residential interior designer Holly Hollingsworth Phillips uses to describe her personal style. These same descriptors perfectly capture our newest design, The Evil Eye boot. It features our most intricate inlay to date, which felt appropriate to treat as a design project of its own—a labor of love that required ample time and underwent trial and error. Similarly, Hollingsworth Phillips' family home, which was originally her childhood home, now serves as a glimpse into the designer's mind and a testament to her mastery of the art of the unexpected.

As a long-time wearer of CITY Boots and a loyal supporter of the brand, Phillips was the ideal person to launch this boot with. We consider The Evil Eye to be the most exciting release thus far, and we believed there was no better location to photograph the product than Holly's home—a place where excitement awaits around every corner. We sat down with Holly in between shots to learn more about her amazing work, and a bit more about the designer herself.

Holly Hollingsworth Phillips in her home, shot by Christina Hussey. 

"I have loved design and fashion for as long as I can remember. Interior design is a curation of personal style for the home. I think it is a natural extension of fashion. I also get to shop for a living… What could be better? "

Holly Hollingsworth Phillips in her home, shot by Christina Hussey. 

Holly, When did you discover your love of design?

I guess you could say my love of design is genetic. My mother, Nancy Hollingsworth, is a retired interior designer who specialized in English Country style. I went to Europe on my first buying trip at age 11, and I guess you could say the rest is history. 

What life moments and achievements are you most proud of?

Professionally, I think running my own design business for 25 years has been a huge feat! Personally, seeing my three children thriving and following their passions is so fulfilling. I also love that I picked up riding again as an adult and adore my horse, Chief. Downtime during COVID gave me the gift of riding again that would have never happened otherwise.

"I love the idea of this boot as a protective element or armor for your day."

Participating in CITY Boots' first ever collaborative product launch is such an exciting experience. I've had the opportunity to explore some amazing destinations around the world, including one of my most recent adventures in Egypt. It's fascinating to witness diverse cultures embracing the Evil Eye as a symbol of protection. When you exude confidence in what you wear, it empowers you in extraordinary ways. The design of these boots is not only remarkable and one-of-a-kind but also intricately crafted. The construction of this particular boot perfectly aligns with my personal design aesthetic, making it truly resonate with me.

Holly Hollingsworth Phillips in her home, shot by Christina Hussey. 

How do you like to style your City Boots?

I love City boots with just about anything! I have worn them with everyday dresses, jeans and even with a sequined dress to a black tie event. The most unusual place I've ever worn my boots was probably a  Harry Styles concert in Paris. My Magenta and Bone Heart boots definitely fit the “Love on Tour” aesthetic perfectly! The best part is they are insanely comfortable right out of the box.

We love your love of travel, where do you feel you’ve gained the most inspiration and where would you tell our followers they MUST visit at some point?

I've been fortunate enough to visit Egypt, Jordan, and Morocco just this year, so this question is quite challenging. However, my upcoming trip to India in December adds another layer of anticipation.

Morocco holds a special place in my heart as a truly enchanting and magical place that everyone should experience. The Medina is a mesmerizing maze of inspiration, art, architecture and shopping galore. What truly sets Morocco apart, though, is the exceptional kindness of its people. Their warmth and hospitality are truly remarkable. Moreover, my journey to the Atlas Mountains and a visit to a local Berber village provided a powerful insight into alternative ways of life. As an American, it's evident how heavily reliant we are on technology and our phones. In contrast, the Moroccan people embrace a simpler, more authentic existence, firmly rooted in their trades and crafts.

Holly Hollingsworth Phillips in her home, shot by Christina Hussey.