Jenna Lyons begins her post-J.Crew chapter with an HBO Max present and sweetness model

Few designers have become as synonymous with a brand they didn't create as Jenna Lyons did with J.Crew.

Lyons spent 27 years at J.Crew, working his way up from assistant designer to president and creative director. During this time she – along with CEO Mickey Drexler – transformed the brand and landed on the New York Fashion Week calendar in 2008 and on the first podium, where Michelle Obama wore a pair of J.Crew gloves.

Throughout her tenure with the company, but especially over the past decade, Lyons herself has become J.Crew's public face and most prolific brand ambassador. Her own style became synonymous with the J.Crew look of the era: mixed patterns, bright colors and bold details like sequins.

But in 2017 Lyons said she was leaving J.Crew after nearly three decades. She has been planning her next steps ever since, and this year she's literally putting her next chapter out there with the debut of Stylish starring Jenna Lyons, a reality show on HBO Max, as well as the launch of LoveSeen, a line of fake eyelashes.

After 27 years in the same company, entrepreneur and reality star were not the titles Lyon anticipated for their next move. But when an appearance similar to that of J.Crew didn't come off, this was an option she pondered.

"It was almost nine months before I stopped working," she told Adweek. "I realized I hadn't gotten any real calls. People wouldn't say," Hey, I want you to do this job. "I had to think about what I was going to do."

The process of figuring out what she's doing next is in large part what is recorded in Stylish, which premiered on HBO Max earlier this month. On the show, Lyon sees, as she put it, "go after a number of different things and see what happened to them". She does this with the help of her chief of staff Kyle DeFord and stylist Sarah Clary. She works on projects involving a photo booth at the SAG Awards and the interior of a Brooklyn townhouse. Along the way, prospective employees look to work with Lyon.

Lyons admits that figuring out what came after J.Crew required some trial and error, and had more business sense than it probably had to use in the past.

"It's hard to start over. It's humbling and scary," she said. "It's hard to come from a place where I not only was the boss but also knew how to get my job done . I knew who to call, how to operate the system. I understood how things were done. All of a sudden I was completely new to everything and I was struggling. It was really a good thing to start over and stick with it to remember what it feels like not to know. "

Jenna Lyons at a J.Crew New York Fashion Week presentationGetty Images

In this new era, Lyon is entering a new space: beauty. She partnered with Magnet, a private equity backed holding company, to bring her LoveSeen brand to life.

The project is a personal one for Lyon as she suffers from a disease that affects eyelash growth called incontinentia pigmenti. Additionally, while at J.Crew, she noticed a hole in the market for women who had a "pretty, very calm approach to beauty with little to no makeup," but who loved the look of false lashes – just like her She found women wearing more dramatic makeup looks. Eyelashes were the common denominator.

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