In a hyper-stereotyped society like the current one, where we all frequently fall into the temptation of pigeonholing people, the reality is that appearances are deceiving and surprises are always the order of the day.

For Jessica Simpson, it's all about surprises these days.

Simpson grew up in a generation full of superstars, such as Christina Aguilera, Britney Spears, Ryan Gosling and Justin Timberlake, which always brought her under the magnifying glass of the tabloid press.

Attention also flocked as she was part of the reality show, Newlyweds: Nick & Jessica, in which a 23-year-old Simpson shared her first marriage experience to millions of viewers. On the show, Simpson showed herself as a loving and naïve young woman, where she was often perceived as someone who did not have to be taken very seriously.

Now at 41 years old and married to former NFL player Eric Johnson, with whom she has three children, Simpson is the owner of successful fashion company, the Jessica Simpson Collection, and is recognized as a successful, creative and powerful businesswoman. Her clothing and lifestyle brand earned her $1 billion in annual sales in 2012.

All 3 kiddos sadly had a 6 day stomach bug so Eric and I desperately needed a long nap and a resurgence night away! 💚 pic.twitter.com/MYQERUAmKD

— Jessica Simpson (@JessicaSimpson) February 20, 2022

Taking note of her success, Entrepreneur dedicated its March cover to her, celebrating Simpson's talent for business, as well as her tireless drive to make dreams a reality.

“Being underestimated is the superpower. It makes you want to soar over everyone. But really, it’s better to do it patiently. I play along in a way that I let people know I’m playing along,” Simpson said.

Fashion Emporium

In 2005, Simpson and her mother, Tina, created the fashion company together with Vince Camuto, then a renowned footwear titan and co-founder of Nine West and the multi-brand conglomerate Camuto Group, which was later joined with the public company Sequential Brands. The move brought Simpson to the stock market for the first time.

After the fall of Sequential, which led them to declare bankruptcy in 2021, Simpson and her mother bought their brand again, paying $65 million. 

“So many men in suits have made me feel underestimated, at this point I just have to laugh, like, ‘Oh, you need a hug,’” Simpson said. “I can’t even think of one moment in particular because it’s happened my whole career. I was always the little girl who had to come in and sit with men in suits, you know? But now I get to wear the suit.” 

Jeff Howald, chief financial officer of the Jessica Simpson Collection, stressed to the publication that “Vince (Camuto) had an eye for the smallest details, and so do Jessica and Tina. Tina attends all the product meetings and Jessica is at many, giving feedback to licensees. A lot of celebrities want to sign up and let everyone else do the work, but Tina and Jessica really work with the brand.”

Her Own Brand 

“We knew we wanted it to be affordable. We never wanted to be in Neiman’s or Bergdorf’s or anywhere like that. We wanted to hit the mid-tier because those are her fans. Those were the people coming to see her shows and buying her records. And Jessica’s personal style and the way she dresses are really pretty happy. It’s approachable and attainable,” Tina stressed, assuring that her collections have always been "a balancing act" between what her daughter would personally wear, and the trends that her potential clients are looking for.

According to statements from Tina and Howald, one of Simpson’s great qualities is her ability to be in tune with her surroundings even if sometimes it seems that she is not.

“We’ll be sitting in a board meeting and I’ll think she’s not listening to anything because she seems really checked out,” Tina said. “But then all of a sudden, she’ll come out with the most brilliant question that’s been asked all day. I’ve always thought her mind processes things differently from other people.”

Being underestimated … it’s like a shield

“When people overlook and undervalue you, they’re leaving you to prep yourself for the future you want. Don’t put too much pressure on yourself because it’s never make-or-break, you know? There’s always a way to make that break. Let time move a little slower so you learn and grow along the way. Then, by the time you get there, you’ll be ready,” the successful businesswoman concluded.