After nearly three decades in the limelight, it seems no one knows how to master personal style quite like multi-hyphenate star, Jessica Simpson.
The founder of her own fashion brand, the actress has always sparked headlines with her best-dressed list taste, a skill she said she honed through years of trial and error.
“I have had many wardrobe malfunctions and fashion mishaps, but I believe that is how we find our fashion sense,” Simpson once quipped per Yahoo! Money. “We have to [experience] the good, the bad and the really ugly.”
Yet even amid these extremely rare mishaps, it seems Simpson has made her mark on the fashion world, regularly wow-ing fans with her impeccable — and quintessentially Jessica — sense of style.
From her unforgettable Daisy Dukes to her show-stopping “Barbie-core” look, here are five of Simpson's most iconic looks.
Pretty in Pink!
Long before Valentino's signature shade of pink hit the runway last fall, singlehandedly sparking the "Barbie-core" trend that has taken both TikTok and Fashion Week by storm, the aughts icon "Took [Our] Breath Away" with a chic monochrome pink moment.
In early 2020, the actress made headlines after taking to the streets of New York CIty in a Barbie-pink patent leather coat, complete with matching fur accents and a waist-accentuating belt. The star completed the look with a hot pink tote bag, a pair of carnation-colored shades, and a series of silver accents, adding an extra icy feel to her ultra-feminine ensemble.
Daring Daisy Dukes!
Of all of Simpson's most iconic fashion moments, none come to mind quite as quickly as the cute country look the "Public Affair" songstress rocked while portraying Daisy Duke in the 2005 comedy, The Dukes of Hazzard. Despite appearing effortlessly chic throughout the flick, sourcing the perfect shorts was quite the task, the star telling storied entertainment reporter Wilson Morales that she tried on "over 100" options before settling on a winning pair.
"It had to fit perfectly," the star recalled . "The girls had to like it and the guys had to like it. And I had to like it, or else I wouldn't have been able to walk with confidence, which would speak for itself."
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Cute In Cheetah!
Though several aspects of her style have changed over the years, one element of Simpson's style has endured through the decades — her love of animal print.
In early 2020, the star stunned fans and the paparazzi alike by turning up to a taping of The View rocking an earthy look, layering a patterned, feather-detailed vest atop a 3/4 length cheetah top. She completed the look with a large pair of sunglasses and a pair of classic black pants.
Beyond winning the award for Choice Breakout Artist, Simpson walked away from the 2000 Teen Choice Awards with yet another title — best Y2K fashion inspiration. Rocking a nude high-neck tank top and a pair of embroidered low-rise jeans, the "Where You Are" artist's look would still catch eyes in 2022, a testament to both the outfit's timeless quality *and* her signature confidence.
"Overall, my biggest fashion advice starts from within, feeling confident in my own skin," the star later explained, per Yahoo! Money.
Sensual In Snakeskin!
But it's not just cheetah print — beyond her signature animal print, Simpson has also dabbled in snakeskin, a pattern that comprised one of her most swoon-worthy style moments. In early 2020, the star was spotted dropping by Jimmy Kimmel Live! donning a white monochrome snakeskin bodysuit with matching sunglasses.