Jarring Photos Of Jessica Simpson That Make Us Miss Her Pre-Plastic Surgery Face

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Jessica Simpson's face transformation over the years hasn't gone unnoticed. Her fuller lips and flawless skin have encouraged speculation about the singer's possible use of cosmetic surgery. A tragic detail about her pop star image is that, since she was 19 years old, her looks have often taken center stage. Living life under the media's microscope, Simpson has faced incredible scrutiny over the many years that she's been a public figure. 

As an adult, the mother of three has opened up about the dangers of strict beauty standards, which she believes to be perpetuated by social media. "What we're doing on social media is creating this idea of what is beautiful and setting up our lives artificially — to look good for who?" she shared with Bustle in 2023.

Simpson's own stunning transformation has encouraged this idea of artificial beauty with questions about her changing appearance when the star was already stunning to begin with. It can be complicated to understand what drives gorgeous individuals like Simpson to turn to cosmetic procedures to enhance their looks, but it is undoubtedly a personal decision. That said, Simpson's pre-plastic surgery face was beautiful, and these photos are a reminder of that. 

Joining other celebs on the 1999 Billboards Awards red carpet in Las Vegas, Jessica Simpson had already made her mark as a young pop star. Just a few months prior to the awards held in December, Simpson became a household name with her single "I Wanna Love You Forever" and her album "Sweet Kisses."

Simpson's Billboard's appearance gave the young singer a total Barbie moment with her long blonde hair and perfectly glam makeup. In the photos from that night, Simpson's warm brown eyes and big smile were undeniable flaunts of her natural good looks. 

For her 20th birthday in 2000, Jessica Simpson hopped on Z100, a radio station in New York, for some b-day celebrations. The gorgeous young pop star was photographed at the DJ desk with her golden locks pinned back and her beaming grin on full display. 

With her head propped in her hand in a seemingly candid pose, Simpson's beauty took center stage. Her clear complexion and smooth skin radiated the pop star's youthful beauty, and her glowing expression showed off her bubbly personality. 

The "Irresistible" singer was among the many stars who attended an MTV event honoring Janet Jackson in March 2001. Flashing a newer, trendier image, with some texture to her hair and a few chunky highlights that were the perfect match for her sun-kissed skin, gave Jessica Simpson a total beach babe vibe. 

The playful pose she hit while photographed on the carpet, biting her tongue while giving her signature big smile, drew attention to her strong cheekbones. Simpson's ability to pull off both the fair-skinned Barbie look and the California stunner proved her natural beauty was the real star. 

In the bitter cold of January 2003, Jessica Simpson took to Veteran Stadium's field to sing the National Anthem. Bundled up in an adorable pink fur coat, one may have expected the singer's complexion to be reddened around her nose and cheeks, but Simpson was far from splotchy. 

Having warmed her hair color and softened the chunky highlights since 2001, the better blended locks and clean girl makeup gave Simpson a completely fresh look. Giving girl next door, she flashed the small dimple on her cheek that was oh so iconic. 

In June 2003, Jessica Simpson released her book "I Do: Achieving Your Dream Wedding" and held a book signing at Planet Hollywood in New York. For the event, Simpson's big blonde curls debuted a new tone, with cool blonde roots and a warm, almost reddish ombre around the ends. The new look framed Simpson's strong cheekbones and chocolatey eyes perfectly. Her skin glowed and she once again flashed her signature big smile that was the epitome of natural beauty. 

2005 was a big year for the singer, as she took a step in the business direction with her launch of The Jessica Simpson Collection. She looked extra refined when she walked the Pre-Grammys red carpet that year with then-husband Nick Lachey. 

Simpson's soft glam for the high-profile party was just perfect. Her peach-toned lip balanced the glow of her tanned skin and her Barbie blonde hair, making her look like an old-Hollywood movie star. Soft makeup made the singer's brown eyes really pop, and enhanced her naturally strong features.

While walking in New York in 2005, Jessica Simpson smiled before the cameras in a gorgeous glammed-up look. Simpson made being a superstar look easy. Rarely without her full smile and flawless complexion, she radiated a softness with her polished image. 

Simpson took another leap in her stunning hair transformation as well, with a new icy blond shade. The hue contrasted her bronzed skin and brought out the deep color of her eyes, proving that even in full glam mode, Simpson's natural beauty would always shine through.