Whether it’s Denver or Colorado Springs, the Centennial State is a core part of my U.S.-travel fandom. While recently revisiting The Mile-High City, I wanted to meet Jessica Caldwell—in person this time. Originally discovered her and her work (check out my first interview in 2014) via Twitter where I noticed a (former) feature about “Independent fashion design for modern, badass women.” She ran her apparel business Machine Apparel—where the spare and sharp aesthetic, expressed throughout its collections, appealed greatly to me.
Today, Jessica designs outerwear for The North Face.
Here at Design Feast, learn about a few main aspects about how she made such a gritty, at times harrowing, all-around exciting, transition from fashion business founder to joining one of the world’s best clothing brands.
You were an independent designer for how long? Five years? Which is a lot of time. Each of those years was definitely dense with your hustling, your grinding. Bootstrapped. You’re in it, totally. You were your own kind of war room, so to speak. You're in the trenches.
When you made that shift from independence to entering the world of a renowned, popular, formidable fashion brand, what were those independent fashion design sensibilities that stuck with you as being more true now than it was then? What were those practices as an independent, hard-working fashion designer and maker that you still carry with you—that you still tap into in your role at The North Face?
I had my own line, Machine Apparel (samples from fashion collections below), just about four years. It was a rollercoaster of creativity–lots of experimenting, trial and error, and working with very limited resources to make things happen. I still look back at that time as one of the most creative periods in my career, because it was total freedom. There were a lot of ups and downs though—as I navigated my way through building a creative business.
Working for myself really helped me develop all those key skills beyond design that I still implement daily. I had to self-manage, know how to jump back and forth between many types of tasks (marketing, accounting, operations, etc.), and still find a way to satisfy my creative side as well. Working at The North Face keeps me on my toes in the same ways. I’m working on multiple seasons at a time in all different stages of development, I’m going to fittings, talking with athletes, and still sit down and actually design product! I’ve learned to stay flexible, organized and to ride each wave as it comes.
Everyone has their own information architecture. I would be very curious to see how you not only collate but also curate your collections of stimulation. Because one of your independent practices, which you still carry through, is your persistent scouting and collecting of inspiration.
When I was a kid, I used to cut out pictures from magazines and save them in a shoebox. Then I’d craft these big collages on the walls of my bedroom. I still do that today, only now it’s all digital. I am constantly saving posts from Instagram. I’ve got my Pinterest algorithm dialed, and I always have a notebook with me to write down ideas, or quotes from books, songs, etc. I’m constantly taking photos when something catches my eye too—my camera roll is a …
