I want to tell you how this conversation came about. I flew into Dallas less than 48 hours before we sat down together. Couldn’t sleep. Went down the Jenny B. Davis rabbit hole at some hour I’d rather not admit to — her styling work, her writing, her career history — and by the time I put my phone down I had about ten thousand things I wanted to ask her. That’s a good sign, in my experience. The best conversations start before they start. Jenny is a licensed attorney, an award-winning journalist, a published author, an editorial fashion stylist, a professor at SMU, and — I want to make sure this gets the attention it deserves — a certified Star Wars cosplayer who has performed at Star Wars Celebration in Chicago and London. She has attended New York Fashion Week every year since 2007. She has been photographed by Bill Cunningham. She launched two fashion lines of her own, earned a Macy’s Emerging Designer placement, and got a New York Times write-up. She is currently in her third year of a doctoral program at SMU while working full-time. She grew up in a hippie household with a potter mother and a history professor father who made beer and grew grapes. She was a German major at Arizona State. She went to law school because she didn’t want to spend her life worrying about money — and because, as she puts it, law school doesn’t teach you the laws. It teaches you how to find things, how to think, and how to work your ass off. She never planned to be an entrepreneur. She calls herself the accidental one. What struck me most in our conversation — and I’ve been thinking about it since — is how Jenny describes the through line of her career. It wasn’t a plan. It was a series of discoveries: finding out she could do something, figuring out she could professionalize it, and then doing it. Over and over, across fields that seem unrelated until you meet her and realize they’re completely coherent. Law taught her to think. Journalism taught her to find the story. Styling taught her that clothes are never just clothes — they’re communication, intention, a signal to the room before you’ve said a word. Teaching taught her that learning is different when you’ve lived. She told me that if you don’t feed your brain, your brain eats itself. I wrote that down. She also said something that I’ve been sitting with since we recorded: time passes whether you do the thing or not. She started her doctoral program in her fifties, mid-career, while working full-time, because the time was going to pass regardless. She didn’t want to look back and think — I wish I had done that. I find that kind of thinking clarifying in a way that’s almost uncomfortable. It removes the excuse of timing. It removes the idea that there’s a right moment to begin something. When I looked through Jenny’s styling work the night before we recorded — the work she’s done for 360 West, for clients, for editorial shoots — what struck me wasn’t just the beauty of it. It was that it made me want to buy things. There’s a difference between a beautiful photograph and a photograph that makes you feel something, want something, reach for something. Jenny’s work does the second thing. That’s not a technical skill. That’s a point of view. We talked about Amy — our brand persona, the woman we design for, the filter we run everything through. When I showed Jenny the idea, she got it immediately. She called it a brand persona. I called it a wall of women we’re trying to serve. We meant the same thing. This is the kind of conversation I started The Well-Dressed Mind to have. Not about fashion as decoration, but about fashion as a reflection of how people have built their lives, their identities, and their sense of self. Jenny B. Davis has built something genuinely rare — a career that doesn’t fit a category, informed by a life fully and curiously lived. We’re eventually doing a part two. There are still about ten thousand things I want to ask her. — Lindsay Listen to this episode of The Well-Dressed Mind wherever you get your podcasts. And if you don’t feed your brain, your brain eats itself. Consider yourself warned. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lindsaynixx.substack.com
