The Complete Transformation Of Jessica Simpson

Jessica Simpson shot to fame in 1999 after touring with the boy band 98 Degrees and quickly became one of Y2K's biggest pop stars with her hit single "I Wanna Love You Forever." Singing has been her passion since she was young, and she honed her skills in church. "Definitely gospel's the core of my music and ever since I can remember, I've been singing so it's definitely a part of who I am," Simpson stated in a 2000 interview on the Teen People Party red carpet.

Over the years, Simpson found much success with her music career and set herself apart from other singers with her country good-girl image, complete with simple denim jeans and white tank-tops. She's always maintained her signature blond locks and Western staples, but she's also occasionally experimented more with her look, opting for bright colors and delicate patterns along with her go-to cowgirl-inspired Westerncore knee-high boots. "I have always loved to incorporate Western details and my Texas roots into both my personal wardrobe and the Jessica Simpson Collection," she told Footwear News in 2024, speaking of the clothing brand she started in 2005. 

While her iconic relationship with 98 Degrees singer Nick Lachey back at the turn of the millennium launched Simpson to superstar status, the two eventually divorced, and Simpson was regarded as one of the ditziest stars out there. But despite the challenges, she became one of the biggest business tycoons of her time. Although the "Irresistible" singer is no longer selling out concerts, she's come a long way since the start of her career.

Jessica Simpson's success didn't just happen overnight, although it appeared that way with the rise of her popularity in the early 2000s. Just like many pop stars, she had to open for other big names before she could headline her own show. After touring with 98 Degrees, she opened for Ricky Martin's Livin' La Vida Loca Tour in 1999. "It is so awesome. His fans are just amazing. They love his music and they really have been responding to me well, which I look at as a blessing," Simpson gushed to Access Hollywood. Just 19 years old at the time, the pressure was on to win the audience over. By then, her "Sweet Kisses" album had already dropped and she was well on her way to being the main act.

Simpson got her wish in 2001 when she headlined her first show in Corpus Christi, Texas, for her DreamChaser Tour. She told the Temple Daily Telegram, "This is something I've dreamed of my whole career. It stinks to be the opening act. Now I'm the one making the decisions. It's kinda scary, but also exciting, and rewarding, and very hectic, all at the same time." She added, "I've had four years of growth since my first album. I want people to realize I'm not an artist who can be overlooked or who can be lumped in with other (teen) artists." At the time, Simpson had begun curling her signature blond hair and moved from Texas girl-next-door white tank tops to Y2K pop star vibes with low-rise glittery bottoms becoming a new staple. 

Back when reality shows were first popularized, Jessica Simpson starred in one of her own with her then-husband Nick Lachey. "Newlyweds: Nick and Jessica" was filmed just after the pair's 2002 wedding and showcased their life together. While both Simpson and Lachey were stars in their own rights, their star power skyrocketed as a couple. However, it was the "With You" singer who captured the hearts of viewers (and the attention of critics) after asking whether the tuna she was eating was chicken or fish. With the arrival of her first film role in 2005's "The Dukes of Hazzard," Simpson also began wearing more midi-length red-carpet gowns, refining her style from pop and reality star to movie star. This was also when she became an official entrepreneur, having launched the Jessica Simpson Collection.

Unfortunately, Simpson and Lachey were victims of the reality television curse and divorced in 2006. That's when Simpson became one of the many celebs who drastically changed their hair after a breakup. "I just chopped it all off. I was going through a divorce and I just said take it all off," she recalled to Footwear News. She shared with ET in 2020 what led to her split with Lachey, explaining that it was partly due to her fame after "Newlyweds" aired. "He's also eight years older than me so he was already so grown up when I wasn't, so once I started to, you know, get covers and get endorsement deals that were separate from him — 'cause we did everything together — there was a little bit of tension," Simpson revealed.

Five years after her divorce from Nick Lachey, Jessica Simpson began dating NFL player Nick Johnson. In 2012, the two welcomed their first daughter together, Maxwell Drew, and just seven months later, Simpson was expecting again with their son Ace Knute. She and Johnson tied the knot in 2014 with their two children being part of the wedding. Simpson's focus was now her marriage and growing family, and the majority share of the Jessica Simpson Collection was sold to Sequential Brands in 2015. During this period, her hair maintained its platinum hue but switched up from shoulder-grazing in 2010 to long and flowing for most of the following decade. Her maternity fashion leaned on the safer side with mainly muted colors and ample coverage, though she wasn't afraid to opt for form-fitting pieces that showed off her silhouette. 

Simpson and Johnson became a family of five when they welcomed their third child Birdie Mae in March 2019. After that, the "Employee of the Month" star was done. "I have no baby fever. The third pregnancy for me [in 2019], that was it. I can't do that again. The last pregnancy for me was really hard," she told Us Weekly in 2022. Still, Simpson has absolutely no regrets about having Birdie Mae. She stated, "I got a great child out of it who I adore and love and she rules the house. She definitely is the most heard in the family." 

Jessica Simpson has been open about her struggles with her weight and body image since having kids, and after giving birth to Birdie Mae, she celebrated a milestone. "6 months. 100 pounds down (Yes, I tipped the scales at 240) My first trip away from #BIRDIEMAE and emotional for many reasons, but so proud to feel like myself again. Even when it felt impossible, I chose to work harder," the entrepreneur shared in a 2019 Instagram post.

Simpson kept up her hard work and shared another win in 2022 with a bikini selfie. "I have gained and lost 100lbs 3x so I never thought this moment could or would happen, but I'm finally spring breakin' wearin' a BIKINI!" she proudly wrote. In a 2022 appearance on "The Real," Simpson told the hosts that she focused on small goals at a time to keep herself motivated to lose weight. "Being in a bikini was never my main goal. I mean, I did that in my 20s," she said of her selfie. The pop star revealed that while on a trip, she packed bathing suits without thinking she'd feel comfortable enough to wear a bikini, but upon trying one on, she saw the results of her body transformation. "I wanted to share it with everyone because I was very proud of myself for doing what at times felt completely impossible," Simpson declared. This period was also monumental for Simpson's career, since together with her mom, she bought back the majority share of the Jessica Simpson Collection for $54 million, which had since become a billion-dollar business, in 2021.

From a (so-called) ditzy reality television star to running a billion-dollar company, Jessica Simpson's rise to the top is quite impressive. Although she hasn't released any new albums since "Happy Christmas" in 2010, the Daisy Duke portrayer has been busy with the Jessica Simpson Collection. In spring 2024, she launched her country-western line and told Footwear News, "I am excited that Western elements are having a moment right now, but for me, it has never gone away. I'll pick a fringe jacket, turquoise belt, and cowboy boots over just about anything else." The collection shows off Simpson's country couture essence perfectly with sandy, neutral tones, fringe, and of course, denim shorts. "I like to style my cut-offs with any and everything — from an oversized T-shirt and some slides around the house to a cute boot and button down, or even a blazer," she shared with the outlet. 

Fans of Simpson's music will be excited to learn that she may be coming out with something new soon. In April, she cryptically shared a photo on X, formerly known as Twitter, of herself wearing headphones and holding a microphone. "The new album we've been waiting YEARS for?!" a fan asked. "Too excited for this! It's been such a long time coming, can't wait to finally see a comeback," another replied. Jessica Simpson singing again? We're all for it.