Jessica Simpson Then & Now: See Photos of the Star

By:

Christina Casiano, Jessica Acosta

December 19, 2014 1:03PM EST

LOS ANGELES, CALIFORNIA - FEBRUARY 04: Jessica Simpson attends the Jam for Janie GRAMMY Awards Viewing Party presented by Live Nation at Hollywood Palladium on February 04, 2024 in Los Angeles, California. (Photo by Araya Doheny/Getty Images for Janie's Fund)

Getty Images for Janie's Fund

Jessica Simpson has been a prominent figure in entertainment for more than 20 years. Explore her career and growth over the years.

Jessica Simpson has been in the spotlight for over 2 decades and has had quite the evolution over time. The Texas girl, born July 10, 1980, has transformed so much over the years, going from a bubbly pop princess to a full-blown fashionista with one of the most successful clothing brands in the business.

She started off embracing 2000s trends, rocking low-rise jeans and baby tees while singing beloved tracks like “I Think That I’m In Love With You” and “With You”. And of course, she became nearly synonymous with Daisy Duke short shorts when she played the hillbilly hottie in the 2005 remake of ‘The Dukes Of Hazzard’. Proving her true fashion prowess, she launched the Jessica Simpson Collection in 2005. The company has made over $1 billion to date.

Click through the gallery to check out photos of Jessica Simpson from her early days until now.

1 of 26

Jessica Simpson Through The Years: See The Star From Her Daisy Duke Days To Now

Jessica Simpson Through The Years: See The Star From Her Daisy Duke Days To Now — Jessica Simpson has been in the spotlight for over 2 decades and has had quite the evolution over time. The Texas girl, born July 10, 1980, has transformed so much over the years, going from a bubbly pop princess to a full-blown fashionista with one of the most successful clothing brands in the business.

She started off embracing 2000s trends, rocking low-rise jeans and baby tees while singing beloved tracks like “I Think That I’m In Love With You” and “With You”. And of course, she became nearly synonymous with Daisy Duke short shorts when she played the hillbilly hottie in the 2005 remake of ‘The Dukes Of Hazzard’.

Proving her true fashion prowess, she launched the Jessica Simpson Collection in 2005. The company has made over $1 billion to date.

Jessica Simpson beams while taking questions during a Q&A.

Click through the gallery to check out photos of Jessica Simpson from her early days until now.

2 of 26

Jessica Simpson In 2000

Jessica Simpson In 2000 — Jessica Simpson promotes her debut album at HMV Records in New York City on Jul. 23, 2000. She looked sugary sweet in flared jeans with a baby tank top and pink belt.

3 of 26

Jessica Simpson On Stage In 2000

Jessica Simpson On Stage In 2000 — Jessica Simpson sports a sassy blue miniskirt as she performs during Arthur Ashe Kids Day festivities, at the U.S. National Tennis Center in New York in 2000. She paired the look with sassy go-go boots and a white tank.

4 of 26

Jessica Simpson At The 2000 Billboard Music Awards

Jessica Simpson At The 2000 Billboard Music Awards — Jessica Simpson dazzles in a black mini-dress with off-the-shoulder sleeves featuring a pink metallic fringe at the 2000 Billboard Music Awards on Dec. 4, 2000. Black boots and big hair completed the look.

5 of 26

Jessica Simpson At The 2001 Nick Choice Awards

Jessica Simpson At The 2001 Nick Choice Awards — Jessica Simpson turns heads in shimmering denim at the 14th annual Kid’s Choice Awards on Apr. 21, 2001. She wore her distressed vest and shorts look with Cinderella-style heels.

6 of 26

Jessica Simpson During A USO European Tour in 2003

Jessica Simpson During A USO European Tour in 2003 — Jessica Simpson serenades soldiers during a USO tour in Europe around Nov. 2003. She glittered in a nautical white look with buttons and anchors.

7 of 26

Jessica Simpson At The 2003 MTV Movie Awards

Jessica Simpson At The 2003 MTV Movie Awards — Jessica Simpson looks Greek goddess good at the 2003 MTV Movie Awards on May 31, 2003. She accessorized the drapey pastel number with dangling earrings.

8 of 26

Jessica Simpson Performs On ‘Good Morning America’ In 2003

Jessica Simpson Performs On ‘Good Morning America’ In 2003 — Jessica Simpson charms the crowd outside ‘Good Morning America’ as part of their summer concert series. She stunned in stripes for the event on Aug. 22, 2003.

9 of 26

Jessica Simpson At The 2003 MTV Video Music Awards

Jessica Simpson At The 2003 MTV Video Music Awards — Jessica Simpson is radiant in white at the 2003 MTV Video Music Awards on Aug. 28. She dared to bare by going without a shirt under her jacket.

10 of 26

Jessica Simpson At The 2004 Golden Globes

Jessica Simpson At The 2004 Golden Globes — Jessica Simpson is chic as can be at the 2004 Golden Globes on Jan. 25. Her dress was draped elegantly.

11 of 26

Jessica Simpson At The 2005 Met Gala

Jessica Simpson At The 2005 Met Gala — Jessica Simpson looks lovely in black and red Michael Kors during the 2005 MET Gala Costume Institute Gala on May 2. She teamed her look with a smokey eye and dangling earrings.

12 of 26

Jessica Simpson In ‘The Dukes Of Hazzard’

Jessica Simpson In ‘The Dukes Of Hazzard’ — Iconic! Jessica Simpson stuns in her itty-bitty denim cut-offs during ‘The Dukes Of Hazzard’.

13 of 26

Jessica Simpson At The ‘Employee of the Month’ Premiere

Jessica Simpson At The ‘Employee of the Month’ Premiere — Jessica Simpson looks sweet as can be at the premiere of ‘Employee of the Month’ on Sep. 19, 2006. She starred in the comedy opposite Dane Cook.

14 of 26

Jessica Simpson At The Premiere Of ‘Extraordinary Measures’

Jessica Simpson At The Premiere Of ‘Extraordinary Measures’ — Jessica Simpson is ultra-chic in a black suit at the premiere of ‘Extraordinary Measures’ on Jan. 19, 2010. She teamed the look with a black clutch and an up-do.

15 of 26

Jessica Simpson At A Teen Vogue Event

Jessica Simpson At A Teen Vogue Event — Jessica Simpson glows at Teen Vogue’s 10th annual Fashion University in New York on Mar. 14, 2015. She was chic in an embroidered skirt.

16 of 26

Jessica Simpson At The Outstanding Mother Awards

Jessica Simpson At The Outstanding Mother Awards — Jessica Simpson is sunshine bright in yellow as she attends the 2018 Outstanding Mother Awards on May 11. She was honored with an award at the event.

17 of 26

Jessica Simpson At BuzzFeed

Jessica Simpson At BuzzFeed — Jessica Simpson looks like a Barbie doll as she arrives at the BuzzFeed offices in New York on Feb. 4, 2020. She was wearing a hot pink, fur-trimmed coat by Saks Potts with an Alexander McQueen purse.

18 of 26

Jessica Simpson Signs Her Memoir ‘Open Book’

Jessica Simpson Signs Her Memoir ‘Open Book’ — Jessica Simpson is all smiles as she promotes her memoir ‘Open Book’ in New York on Feb. 4, 2020. The book is a New York Times bestseller.

19 of 26

Jessica Simpson Arrives For ‘The View’

Jessica Simpson Arrives For ‘The View’ — Jessica Simpson is chic in a red snakeskin ensemble as she arrives for a taping of ‘The View’ on Feb. 5, 2020. She teamed the red Alexander Wang dress with a black, leather motorcycle jacket by Balenciaga.

20 of 26

Jessica Simpson Holds Baby Birdie Mae

Jessica Simpson Holds Baby Birdie Mae — Jessica Simpson beams while holding her adorable daughter Birdie Mae Johnson. While mom was chic in heaad-to-toe black, little Birdie was cute as a button in a leopard print onesie during the New York City outing.

21 of 26

Jessica Simpson In 2020

Jessica Simpson In 2020 — Jessica Simpson is so chic in pink and black Alexander McQueen during the Create & Cultivate conference presented by Mastercard at Rolling Greens in Los Angeles on Feb. 22, 2020. She wore a fuchsia jacket over a fishnet turtleneck and was so stylish.

22 of 26

Jessica Simpson At ‘The View’ In 2020

Jessica Simpson At ‘The View’ In 2020 — Jessica Simpson is a full fashionista as she arrives for an appearance on ‘The View’ on Feb. 5, 2020. She wore a wild animal print and feather-trimmed Giambattista Valli jacket with Safiyaa trousers, and a bag by Louis Vuitton.

23 of 26

Jessica Simpson In Nashville In 2020

Jessica Simpson In Nashville In 2020 — Jessica Simpson looks like she means business while at a Nashville photocall for her memoir ‘Open Book’ on Feb. 12, 2020. She wore a fitted brown sweater and toffee-colored slacks with a leather belt.

24 of 26

Jessica Simpson In NYC in 2020

Jessica Simpson In NYC in 2020 — Jessica Simpson goes full Gucci while out in New York on Feb. 6, 2020. She wore a red jacket with black and white trim along with a rainbow cursive emblazoned blouse and Dalmation-inspired purse.

25 of 26

Jessica Simpson & Family In NYC

Jessica Simpson & Family In NYC — Mommy and me! Jessica Simpson and Maxwell Drew Johnson look so chic together while out in New York on Feb. 5, 2020. Mom wore a red suit with a cape and Max donned a cool orange, red, and plum jacket.

26 of 26

Jessica Simpson In Red

Jessica Simpson In Red — Jessica Simpson shows off her striped purse while out with her family in New York on Feb. 5, 2020. Her hair was in a deep side part and she had on earth-toned makeup.

Click to Subscribe to Get Our Free HollywoodLife Daily Newsletter to get the hottest celeb news.