Jessica Simpson's 11 Best Music Video Outfits

With her booming, multidimensional lifestyle business and enviable Instagram account filled with images of an adorable young family, it is remarkably simply to forget that Jessica Simpson's career (including Jessica Simpson's enviable outfits) began with a singing gig. With chart-topping tween anthems like "Come On Over" and "I Think I'm In Love With You", Simpson ruled the radio in the early aughts. However, the chanteuse's vocals weren't the only quality audiences found irresistible.

Next to Britney Spears, Mandy Moore, and Christina Aguilera, Simpson subverted the music video scene with improbable, choreographed dance routines and avant-garde, space age setups, all while clad in a series of artfully alluring and beautifully bizarre getups. Opulent, fur-lined duster coats jostled for attention with terrycloth roller derby rompers, colorful cowboy boots became a style signature of Simpson's, and crop tops graced each and every video nearly a decade before the trend's resurgence last year. To say the sartorial direction of Simpson's videos was dapper would be a misnomer, but the singer's style inarguably had a certain je ne sais quoi. In honor of the designer/singer/street style maven's recent business achievements, scroll through for Simpson's finest fashion moments via music video. After all, not everyone can rock Daisy Dukes like a boss.

1. The Dukes Of Hazzard Duds

Perhaps no ensemble of Simpson's has achieved greater fame than the micro-sized jorts and distressed tee the singer sported for a memorable cameo in Duke of Hazzard, and made a subsequent repeat performance in her "These Boots Are Made for Walkin' " video.

2. The Knotted Cropped Blouse

Although Britney Spears' schoolgirl ensemble, complete with its twisted white Oxford top, took center stage in the seminal 1999 hit "...Baby One More Time", Simpson took on the same trend for her own 1999 solo "I Think I'm In Love With You". Two might qualify as a trend in this rare circumstance, but the belly button-baring white button down is a fad to be approached with caution.

3. The Casual Khaki And Denim Getup

What could be more millennial than a denim jacket paired with a crop top and white khaki pants? Simpson graced the video of "I Wanna Love You Forever" in an outfit befitting her girl-next-door image, complete with a single propeller plane as an unexpected accessory.

4. The Rad Rainbow Ensemble

The '70s were alive and well in Simpson's "A Little Bit" video, where a rainbow-striped halter top, knee socks, and a periwinkle mini skirt belied the film's bizarrely futuristic aesthetic.

5. The Bizarre And Bold Americana Outfit

"A Little Bit" had more to offer than quirky halters and scrunchie-adorned pigtails. Ripped graphic tees and what appeared to be the Ultimate Fighting Champion belt made a cameo in the video as well.

6. The Fur-Trimmed Duster Jacket

No music video career is complete without a floor-grazing, fur-trimmed coat, even if the film in question isn't quite '90s gangster rap.

7. The Red Roller Derby Romper

Simpson got her skate on — and bewitched one lucky roller rink attendant — in a minuscule terrycloth romper and layered necklace paired with tousled curls for her "A Public Affair" video.

8. The Patriotic Pinup Look

Simpson struck sartorial gold — and gave a nod to her nationalistic spirit — in an American flag-adorned tank top and gritty denim mini skirt accented with reflective shades.

9. The Blinding, Blinged-Out Crimson Outfit

Those who believe light sabers aren't an appropriate accessory are sorely mistaken, at least according to Simpson and her stylist. A crimson crop top and red, white, and blue belt lent vibrance to Simpson's outlandish attire, but the heavy gold ornamentation and glowing light stick stole the show in the chanteuse's "A Little Bit" video.

10. The Daring Leather Dominatrix Ensemble

The black leather crop top and hip-slung trousers Simpson sported for her "Irresistible" video were likely fittingly enticing to Simpson's adoring male fan club, but sartorially speaking, the getup lacked dimension — and subtlety.

11. The Backless Black Jumpsuit

Simpson declared her well-publicized love to then-hubby Nick Lachey in a back-exposing black jumpsuit with a Studio 54 vibe for her "Where Are You" video. Ah, to be in love in the early aughts.

Images: jessicasimpsonVEVO/YouTube (11)