Jessica Armstrong Headshot

Jessica Armstrong ‘02 first experimented with styling as a teenager, dressing up friends and staging mock photo shoots. This continued through college, as Jessica became more involved in UCSB’s Art department. After graduating from The Fashion Institute of Design and Merchandising in San Francisco in 2005, she hit the ground running as an intern on various projects in Los Angeles.

Now with nearly two decades of experience under her belt, Jessica has established herself as a freelance fashion stylist for brands such as Adidas, Netflix, and Coca-Cola. Creative freedom and control over her schedule are two sweet rewards for her years of hard work. 

Q: Upon earning your Bachelor of Arts degrees in Art Studio and History in 2002, were you already envisioning a future career in the fashion industry?

When I studied at UCSB, my goal at the time was to become a fashion photographer. Growing up in Northern California, I didn’t have access to Los Angeles and the industry over there. My emphasis was in photography because I thought that the only way to work in fashion was going to be through magazines.


Q: How did you further your passion for fashion as an undergraduate student? (Clubs, classes, etc)

I made all my friends model for me! I was always doing mock photo shoots for classes and for fun. I also always volunteered for any extra opportunities in photography training or exhibition walking.


Q: What is the most rewarding aspect of freelance work? Most challenging?

I have been working freelance now for almost 12 years. Before this, I held a corporate job working as a fashion designer for a small manufacturing company. I realized I did not like how the computer work felt monotonous. I found myself looking at my calendar and counting down the months before three-day-weekends. The biggest reward in switching to freelance is that you get to be your own boss. I really enjoy that freedom, along with getting to travel for work and take time off. I work really hard and then I take time off. I probably work seven to eight months out of the year. 

The most challenging aspect is the feelings of imposter syndrome when the industry is slow. You have to have faith in your skills, connections, references, and the universe that you’re going to continue booking jobs. 


Q: Describe a typical day or session of personal styling with a client. 

I do a few different types of styling. The first is working on ad campaigns. This is when I am given a creative deck for guidance in order to put together a wardrobe board. With the help of assistants, I shop and organize the clothing for each person or character. Once we decide on the looks, we are ready for set. The days are long – 10 to 12 hours – so that we can run through all of the looks. The last step is one that not many people know about, which is going through all the receipts, paperwork, and Excel spreadsheets to wrap up the job. 

The second type of styling that I do is personal styling for individual clients. This involves more use of my relationships with different brands and designers as they will loan me pieces for borrow and/or purchase. I just did this for a client attending the Oscars’ Elton John After Party. One of my favorite aspects about this job is that the days are never the same. I am always working with new and different people. 


Q: What has been your favorite work project to date? 

When I first moved to New York to learn about styling, I started assisting a stylist for Serena Williams. I was a tennis player in high school, so I thought that was so exciting. As I got to know her, I began going to her home to get her ready for parties and events, which was a “next level” moment for me. I also really enjoy travel jobs because I stay in nice hotels and go to work in beautiful locations. 


Q: How has the landscape of the fashion industry evolved over the course of your career?

The biggest change has been due to social media. When I moved to Los Angeles, Facebook barely existed. I had to network old-school style by cold calling agencies and production houses until someone agreed to get coffee. It has been an interesting evolution watching how important social media is today. It causes a lot of us to feel pressure because instead of just being a stylist, we’re also expected to be a brand manager or creative director. 


Q: What advice would you give to aspiring stylists who wish to carve out a niche in the fashion industry today?

My best advice is to have no ego. Be humble and be thirsty. You have to get after it and work hard. You see a lot of people who expect to get to the top quickly or get paid a lot. But I used to work for free as an intern! You have to work your way up through listening to and learning from others. I’d also recommend working on your book, sharing your styling on Instagram, and creating a website in order to be taken seriously. 


Q: What is on the horizon for you in 2024?

In freelance work, a lot of us like to have multiple sources of income. I have friends who also do staging or real estate. I decided to open an online store, Closet Intuition, which offers styling tools alongside wardrobe & accessories for men & women. Starting this was a way for me to diversify my brand, while continuing to explore my passion for fashion. Our feature product, “Your Stylist On The Go” styling kit, just launched in December.