Forget what you know about Jenna Lyons. Famously dubbed the “woman who dresses America,” she is best known for her role as President of J. Crew, where she worked for nearly three decades dressing women from all walks of life – from Michelle Obama to aspiring fashionistas. Now, three years after her departure from the retailer, the fashion maverick is returning to the public eye in an entirely new way.

Wonder what she’s been working on? You’re about to get an inside look. Today, the formidable designer and fashion executive launches Stylish with Jenna Lyons, her new show on HBO Max documenting her entering a new stage of her life. A mix of elevated documentary and competition show, viewers will follow Lyons as she builds her new business in the home, beauty, and fashion space – aimed at helping people from all walks of life find their own style. The designer will test a diverse group of creative associates all vying for a position in her growing team with various creative endeavors and design projects.

We chatted with the industry veteran and CFDA member about everything from her new beauty line LoveSeen to what we should expect from the show.

How are you?

Hanging in. It’s been a weird one. I’m eagerly awaiting for 2021.

How did this opportunity come about and what made you want to pursue this?

I was having lunch with a friend in Los Angeles, and a man named Matt Hanna spied me from across the room and got my number from said friend. [He] cold-called me and said any interest in TV? I said no. However, in the back of my mind Anna Wintour’s voice came to me at our very first lunch meeting post-J.Crew departure of “you shouldn’t do fashion you should do TV” – so I figured I would at least have a conversation with Matt. I had a conversation with Matt, he asked me to have a conversation with a few network executives, which I did, and one of them was an executive at WarnerMedia. After three conversations, we decided to make a show. I’m not really sure how that happened. I think I spent more time researching a coffee maker. I really didn’t know what I was getting myself into, but for some reason, I took the leap.

How does it feel to be re-entering the fashion scene and what did you learn during your time off?

I don’t feel like I’m re-entering the fashion scene. Producing clothes is very different, and looking at style and commenting on it. I’m not making clothing anymore, and that’s an incredibly different process. What I’ve learned in my time off is that trying new things is hard, but trying new things is incredibly rewarding. Getting a second chance after such a long, singular trajectory is pretty phenomenal.

You’ve also branched out into several areas, including the beauty industry with your new line LoveSeen. What has it been like to venture out on your own?

Absolutely terrifying. I used to know what I was doing, how to get things done, how to fix things, how far to push, where my paycheck was coming from, what my budgets were, and now there is no clear baseline. Everything is new, everything is shapeshifting, and the word vacation barely exists. However, when someone writes a nice review saying that they love the product, it’s literally everything.

Tell us about your team, Kyle Deford (chief-of-staff) and Sarah Clary (stylist). How did you all connect and why was it important for you to show this dynamic on the show?

We connected from our days at J.Crew. It wasn’t just important to show the dynamic on the show; I wouldn’t have done it without them. There’s no world in which you can create anything on your own. I’m not a singular artist who is capable of going to a studio every day and tooling away. I like collaboration, connection, idea sharing. I also am deeply disorganized and need help.

How has COVID-19 impacted your personal style?

I’ve given up on pants and heels, and I am obsessed with necklines and eyelashes due to Zoom.

What can viewers expect to see on Stylish? Any sneak previews you can give us?

Blood, sweat, and tears. It’s primarily transformations, real stories, and a reality show that’s actually real.

What do you hope viewers take away from this series?

That Kyle and Sarah are not perfect (😉), that work can be fun, and a deep desire to watch the next episode.