Jessica Simpson & Nicole Richie's Biggest Style Flops
With hugely successful clothing, footwear, jewelry, handbag, and fragrance lines, Jessica Simpson and Nicole Richie have earned their roles as celebrity mentors on NBC's newest competition series, "Fashion Star" (premieres Tuesday, March 13, at 9:30 p.m.), in which 14 unknown designers battle for a multimillion-dollar prize and the chance to launch a collection. But these trendsetting fashionistas weren't always so fashion-forward. Here's a look back at some of the ladies' most questionable style choices.
Jessica Simpson hit it big with the release of her debut single, "I Wanna Love You Forever," back in 1999. Unfortunately, the outfit she wore to one of her first big events was hard to love. Walking the red carpet at the What's Next party for Teen People magazine, Jess wore a matching pink leopard-print T-and-pants ensemble.
In 2001, Nicole Richie was known more for being Paris Hilton's BFF than a fashion-forward socialite, and photos like this one prove just how far she's come. It looks as though Nicole and Paris had gotten so close that dressing in identical head-to-toe denim for a night on the town seemed like a good idea.
2000 was not a good year in fashion for Jessica Simpson, who had yet to hire Annabel Tollman as her stylist. At that year's Billboard Music Awards, Jess stepped out in a seriously short little black dress and knee-high black boots. A lot of skin, yes, but still cute. What sent this look over the edge were the feathers-cum-floaties adorning her arms. While she didn't fly away, her name flew onto a number of worst-dressed lists.
Jessica Simpson has always tried to stand out in a sea of blond pop stars, such as Christina Aguilera and Britney Spears. Unfortunately, we had a hard time seeing Jessica through the shimmering denim she sported on the blue carpet at the 2001 Kids' Choice Awards. You're the shining star, Jessica, not the clothes!
The getup Nicole Richie wore to EW's annual pre-Emmy party back in 2003 was anything but award-worthy. From the two-toned hair to the shiny blue dress to the motorcycle boots, everything looked either ill-fitting or mismatched. The Emmys are a time to shine, but Nicole missed the mark.
Jessica Simpson's style was all over the place in 2001 -- she even took a trip back to the Middle Ages. At Z100's annual Zootopia show, Jessica stepped out in a bondage-inspired outfit reminiscent of medieval times. Luckily, before long, Jessica started to look forward rather than back in time for fashion inspiration.
2003 marked a new claim to fame for Nicole Richie, who started to promote her signature Southern California-girl style. Unfortunately, when she arrived for the opening of the Miss Sixty store on Melrose Avenue in L.A., Nicole looked like she'd lost her fashion road map: Her skin-baring dress screamed sunny SoCal climes, while the long scarf and mid-calf Chucks were more of a nod to crisp Seattle weather.
A long-sleeved cocktail dress and a bright pair of pumps -- how could you go wrong? Well, unfortunately for Jessica Simpson, a dangerously low-plunging neckline with the potential for a major wardrobe malfunction was enough to cause fashion critics to cringe at Mercedes-Benz Fashion Week back in 2003.
For Nicole Richie, 2003 was the year of wild colors, mismatched prints, crazy hats, and confusing shoes -- all at the same time! On the bright side, at least no one can accuse Nicole of lacking spunk or spirit.
We're not eager for culottes to make a comeback, and for good reason. In 2004, at MTV's Spring Break party, Jessica Simpson sported a stark-white culotte ensemble. Paired with bleached blond locks, a midriff-baring shirt, and strappy white heels, it was almost too much to handle.
We've never fully accepted Uggs as red carpet ready. Originally created for surfers to slip on at the beach, Uggs were intended for sand, surf, and sidewalks, not parties and premieres. Back in 2004, Nicole Richie felt otherwise. Walking the red carpet at the Shaquille O'Neal All-Car Showdown, the star looked a bit too casual for the cameras.
The media had a field day when Jessica Simpson took the stage to perform at a Florida chili cook-off in 2009. The curvy star arrived at the show in high-waisted jeans and a wide leopard belt, inspiring critics to blast the star's fashion sense and physique. But sister Ashlee fought back, saying, "I am completely disgusted by the headlines. All women come in different shapes, sizes, and forms, and just because you're a celebrity, there shouldn't be a different standard." While we agree with Ashlee's point of view, dressing well means dressing for your figure, no matter the shape or size.
With hugely successful clothing, footwear, jewelry, handbag, and fragrance lines, Jessica Simpson and Nicole Richie have earned their roles as celebrity mentors on NBC's newest competition series, "Fashion Star" (premieres Tuesday, March 13, at 9:30 p.m.), in which 14 unknown designers battle for a multimillion-dollar prize and the chance to launch a collection. But these trendsetting fashionistas weren't always so fashion-forward. Here's a look back at some of the ladies' most questionable style choices.
Jessica Simpson hit it big with the release of her debut single, "I Wanna Love You Forever," back in 1999. Unfortunately, the outfit she wore to one of her first big events was hard to love. Walking the red carpet at the What's Next party for Teen People magazine, Jess wore a matching pink leopard-print T-and-pants ensemble.
In 2001, Nicole Richie was known more for being Paris Hilton's BFF than a fashion-forward socialite, and photos like this one prove just how far she's come. It looks as though Nicole and Paris had gotten so close that dressing in identical head-to-toe denim for a night on the town seemed like a good idea.
2000 was not a good year in fashion for Jessica Simpson, who had yet to hire Annabel Tollman as her stylist. At that year's Billboard Music Awards, Jess stepped out in a seriously short little black dress and knee-high black boots. A lot of skin, yes, but still cute. What sent this look over the edge were the feathers-cum-floaties adorning her arms. While she didn't fly away, her name flew onto a number of worst-dressed lists.
Jessica Simpson has always tried to stand out in a sea of blond pop stars, such as Christina Aguilera and Britney Spears. Unfortunately, we had a hard time seeing Jessica through the shimmering denim she sported on the blue carpet at the 2001 Kids' Choice Awards. You're the shining star, Jessica, not the clothes!
The getup Nicole Richie wore to EW's annual pre-Emmy party back in 2003 was anything but award-worthy. From the two-toned hair to the shiny blue dress to the motorcycle boots, everything looked either ill-fitting or mismatched. The Emmys are a time to shine, but Nicole missed the mark.
Jessica Simpson's style was all over the place in 2001 -- she even took a trip back to the Middle Ages. At Z100's annual Zootopia show, Jessica stepped out in a bondage-inspired outfit reminiscent of medieval times. Luckily, before long, Jessica started to look forward rather than back in time for fashion inspiration.
2003 marked a new claim to fame for Nicole Richie, who started to promote her signature Southern California-girl style. Unfortunately, when she arrived for the opening of the Miss Sixty store on Melrose Avenue in L.A., Nicole looked like she'd lost her fashion road map: Her skin-baring dress screamed sunny SoCal climes, while the long scarf and mid-calf Chucks were more of a nod to crisp Seattle weather.
A long-sleeved cocktail dress and a bright pair of pumps -- how could you go wrong? Well, unfortunately for Jessica Simpson, a dangerously low-plunging neckline with the potential for a major wardrobe malfunction was enough to cause fashion critics to cringe at Mercedes-Benz Fashion Week back in 2003.
For Nicole Richie, 2003 was the year of wild colors, mismatched prints, crazy hats, and confusing shoes -- all at the same time! On the bright side, at least no one can accuse Nicole of lacking spunk or spirit.
We're not eager for culottes to make a comeback, and for good reason. In 2004, at MTV's Spring Break party, Jessica Simpson sported a stark-white culotte ensemble. Paired with bleached blond locks, a midriff-baring shirt, and strappy white heels, it was almost too much to handle.
We've never fully accepted Uggs as red carpet ready. Originally created for surfers to slip on at the beach, Uggs were intended for sand, surf, and sidewalks, not parties and premieres. Back in 2004, Nicole Richie felt otherwise. Walking the red carpet at the Shaquille O'Neal All-Car Showdown, the star looked a bit too casual for the cameras.
The media had a field day when Jessica Simpson took the stage to perform at a Florida chili cook-off in 2009. The curvy star arrived at the show in high-waisted jeans and a wide leopard belt, inspiring critics to blast the star's fashion sense and physique. But sister Ashlee fought back, saying, "I am completely disgusted by the headlines. All women come in different shapes, sizes, and forms, and just because you're a celebrity, there shouldn't be a different standard." While we agree with Ashlee's point of view, dressing well means dressing for your figure, no matter the shape or size.
