Jenna Lyons on Her New TV Show and the One J.Crew Piece She'll Never Get Rid Of

HBO Max | Squire Fox

You know Jenna Lyons as the former president of J.Crew who became known as the "woman who dresses America" thanks to her recognizable sense of style. Jenna doesn't just mix high and low pieces, she proves that fancy has its place next to casual and/or funky if you want it to. Her outfits have always inspired us to reimagine our closets, selecting clothes we haven't visited in years because they might look really great with some fresh denim and a pair of heels. Jenna has an air of effortlessness about her that became synonymous with the J.Crew brand — her look embodies sophisticated cool, or, perhaps in J.Crew terms, relaxed prep. While Jenna left J.Crew in April 2017, she's fine-tuning her own business and doing it in the public eye with the release of HBO Max's Stylish With Jenna Lyons, a documentary-slash-reality competition.

"My biggest hope is to peel away the premise of rules in fashion, home, and/or beauty. Everyone has the right and the access; rules just don't apply."

Season one, which begins streaming on Dec. 3, takes us through a handful of design projects that delve into the home and beauty spheres. We see Jenna tackle renovations, makeovers, and the launch of her beauty line, LoveSeen. The kicker? Jenna's showing us the ins and outs of her industry by hosting weekly competitions with aspiring artists and creatives. Each project introduces us (the viewer) and her current team (including Kyle DeFord, the chief of staff at Lyons L.A.D., and stylist Sarah Clary) to associates interested in joining Jenna's staff — for longer than the length of just one episode. Can you imagine the honor? With that, we get to see how Jenna and Kyle interview candidates and choose the right people for carrying out Jenna's vision.

We chatted with Jenna about the show and also asked her to look back on her J.Crew days. As for the future, well, we just had to know how Lyons sees her role changing down the line. Will she always be the "woman who dresses America"? "I think that somehow along the way, there became this idea that there were rules. Rules get people in a place where they feel they can or can't, should or shouldn't. My biggest hope is to peel away the premise of rules in fashion, home, and/or beauty. Everyone has the right and the access; rules just don't apply," Jenna told POPSUGAR. We really like the sound of that. Keep reading to find out more about what she has in store — or, in the case of her favorite J.Crew piece from high school, storage.

HBO Max | Squire Fox

POPSUGAR: You ask your interviewees to put together an outfit because you say it's similar to how they'd style a room. If your living room were an outfit, what would you be wearing?
Jenna Lyons: My son is here listening and he says my Drake's silk pajama top, vintage army pants, maybe a touch of leopard, and a hint of gold.
PS: During the show, we get to watch you build your brand and test creative associates who work with you — what advice would you give to someone who wants to start their own fashion venture? And what's the most important quality you're looking for in a candidate you work with?
JL: Only go into fashion if you are obsessed. I remember distinctly talking to some young students about fashion and I asked them what their favorite era was, and some of the students didn't know about history — how fashion started, where it came from, who Jeanne Lanvin was, or who started Balenciaga. It's important to understand and be obsessed. It's not an easy business, but if you absolutely love it, you won't be looking at the clock. The most important quality in someone I hire is a sense of curiosity and desire to learn. You can't train that, and you can't give it to someone. It's an inside job.
PS: What's the best interview outfit that makes a great first impression, even if it's over Zoom?
JL: I think being comfortable comes first; don't overthink it. Confidence is key in an interview, and feeling like yourself. I don't care if an outfit is wack or super strict. If you feel in your skin and comfortable, you'll do great. These days, I think Zoom has created a whole new approach to communication and visuals. I would say less important from the outfit is lighting and a big smile. I love watching Trevor Noah on his show with his beard and slightly tousled hair and sweatshirt. It makes me love him all the more; he is no less credible in his sweatshirt because he is direct, warm, and engaging.

HBO Max | Squire Fox

PS: What is one thing you learned during your time at J.Crew that's helped you approach the show — maybe even a mantra that you still repeat to yourself to this day?
JL: Your team can be your biggest inspiration.

"I think what I love about fashion today is that with the world of Instagram and social media, there is license to do your own thing. Everyone has an opportunity to shine."

PS: The world has changed so much in a matter of months, and fashion itself is fundamentally different. What's your take on trends in this moment and going forward? Are they as relevant? If not, what is shaping style right now?
JL: Trends are such a funny thing. The things I loved 10 years ago I still love and go back to regularly. My perfect worn-in jeans, my favorite blazer, my simple white shirts. Don't get me wrong, I've dabbled in every trend possible, made some terrible mistakes, and at the end, I feel like we all get whipped around by them. I think what I love about fashion today is that with the world of Instagram and social media, there is license to do your own thing. Everyone has an opportunity to shine.
PS: What is your favorite outfit of all time?
JL: One of my favorite outfits is one that I have the most fond and powerful memories of. It's an outfit I wore to the White House the first time I met the president [Barack Obama] and the first lady, Michelle Obama. It was a simple white shirt with a high-waisted feather skirt, and it's not so much the outfit, but I remember every second of the preparation and lead-up — the handshaking, the picture-taking; the night itself is ingrained in my memory forever.
PS: What's your favorite piece of clothing (or collection) you ever worked on while at J.Crew?
JL: We made an incredible sequin blazer. I think we probably made 25 of them. It never fails me. I've worn it to speaking engagements. It always makes me feel like the Christmas tree at Rockefeller Center. It gets lots of love and has good juju.
PS: What's the oldest J.Crew item you still keep in your wardrobe, and do you still wear it?
JL: I still have a J.Crew anorak I bought when I was in high school. It's somewhere deep in storage. I've never been able to get rid of it. It's still one of my all-time favorites.

Behind-the-Scenes Photos From Stylish Season 1
HBO Max | Squire Fox

Behind-the-Scenes Photos From Stylish Season 1

HBO Max | Squire Fox

HBO Max | Squire Fox

HBO Max | Squire Fox

HBO Max | Squire Fox

HBO Max | Squire Fox

HBO Max | Squire Fox

HBO Max | Squire Fox

HBO Max | Squire Fox

HBO Max | Squire Fox