Monday, February 3

Jessica Simpson’s Hottest Moments: Photos Of The Star’s Best Looks

January 9, 2025 Entertainment 6 Mins Read

Jessica Simpson’s Hottest Moments: Photos Of The Star’s Best Looks

Getty Images for Jessica Simpson

Jessica Simpson has evolved from teen sensation to full boss babe over the years. See her hottest photos of all time here.

Jessica Simpson is an American singer, actress, fashion designer, and author, born July 10, 1980. Jessica got her start by performing in church choirs as a child. After much practice in the music scene, she eventually signed with Columbia Records in 1997 (she was only 16!). She released her debut studio album, ‘Sweet Kisses’ two years later, which sold two million copies in the United States. And she only got bigger and better as time went on. She gained even more fans with her fourth studio album, ‘This Skin’. She dropped it in 2003 and its second track, “With You” topped the Mainstream Top 40 chart.

She was once married to Nick Lachey from the years 2002 to 2006. Today, she is married to former American football tight end Eric Johnson and has three children Birdie Mae Johnson, Maxwell Drew Johnson, and Ace Knute Johnson.

Want to see how Jessica has evolved over her busy career? Click through the gallery to see her transformation.

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Jessica Simpson at W Magazine, Mark Ronson, and Gucci’s Grammy After-Party

Jessica Simpson at W Magazine, Mark Ronson, and Gucci’s Grammy After-Party — Jessica Simpson attended the launch of her Fall Collection at Nordstrom in Los Angeles, California, in 2022.

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Jessica Simpson Celebrates the Launch of her Fall Collection at Nordstrom

Jessica Simpson Celebrates the Launch of her Fall Collection at Nordstrom — Jessica Simpson attended the launch of her Fall Collection at Nordstrom in Los Angeles, California, in 2022.

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Jessica Simson In Pink In 2020

Jessica Simson In Pink In 2020 — Jessica Simpson is stunning in pink at the Create & Cultivate Los Angeles event, presented by Mastercard at Rolling Greens on Feb. 20, 2020. She teamed the slick suit with a fishnet top.

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Jessica Simpson Promotes ‘Open Book’

Jessica Simpson Promotes ‘Open Book’ — Jessica Simpson looks like a boss as she poses during a Nashville photocall during her book tour for the memoir ‘Open Book’ on Feb. 12, 2020. Her high-waisted khakis and fitted brown sweater looked great together.

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Jessica Simpson In 2020

Jessica Simpson In 2020 — Jessica Simpson looks like a a Barbie girl while out in New York on Feb. 4, 2020. Her look was by Saks Potts while her coat and bag were Alexander McQueen.

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Jessica Simpson In Red In 2020

Jessica Simpson In Red In 2020 — Red hot! Jessica Simpson appears at Stella 34 Trattoria in Macy’s Herald Square to promote her new memoir ‘Open Book’ on Feb. 5, 2020.

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Jessica Simpson In NYC In 2019

Jessica Simpson In NYC In 2019 — Jessica Simpson out and about in New York City on September 25, 2019. She worked this black dress on her night out.

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Jessica Simpson In 2018

Jessica Simpson In 2018 — Jessica Simpson wears a Gucci outfit when out and about in New York on April 24, 2018. She looked super fierce.

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Jessica Simpson In 2017

Jessica Simpson In 2017 — Jessica Simpson steps out in a Isabel Marant red leather skirt and Dolce & Gabbana floral sunglasses on August 9, 2017. She stunned in her cute, vintage look.

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Jessica Simpson in 2005

Jessica Simpson in 2005 — Jessica Simpson seen leaving the Bryant Park Hotel after giving a concert at the ‘Good Morning America’ on August 5, 2005. She looked super cute in her iconic Daisy Duke shorts.

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Jessica Simpson Rocks Her Daisy Dukes

Jessica Simpson Rocks Her Daisy Dukes — Short and sweet! Jessica Simpson shows off her legs in a 2005 promo shot for the box office dud ‘The Dukes Of Hazzard’. Still, it was an iconic pop culture moment for Jessica.

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Jessica Simpson At The 2003 AMAs

Jessica Simpson At The 2003 AMAs — Jessica Simpson at the 31st Annual American Music Awards on November 15, 2003. She totally worked her strut on the red carpet!

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Jessica Simpson At the U.S. Open

Jessica Simpson At the U.S. Open — She’s an ace! Jessica Simpson shined on the court during Arthur Ashe Kids’s Day tennis match at the U.S. Open. She wore a white crop top and light blue skirt.

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Jessica Simpson On Stage In 2003

Jessica Simpson On Stage In 2003 — Jessica Simpson is seen performing on ‘Good Morning America’ in Bryant Park in Aug. 2003. She wore a striped top and long skirt.

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Jessica Simpson Performs In 2004

Jessica Simpson Performs In 2004 — Jessica Simpson sang her heart out at the 66th annual Pioneer of the Year Awards on Dec. 13, 2004. She wore a long black dress.

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Jessica Simpson Is All Smiles

Jessica Simpson Is All Smiles — Jessica Simpson rocked a pretty in pink dress at the ‘Here On Earth’ premiere in New York. She also had on matching shoes.

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Jessica Simpson In 2000

Jessica Simpson In 2000 — Jessica Simpson looks like a teen dream while promoting her new CD in 2000. She flashed her tummy in a very-Y2K cami and low-rise jeans combo for the Jul. 23, appearance at New York’s HMV Records.

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