Ranked: Hilary Duff’s Forgotten Fashion Moments From The 2000s

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26. Hit: MTV Icon Gala 2002

While Hilary was obviously quite new to the red carpet and fashion in 2002, we do have to give her credit for this simple button-up and jeans look she wore to the MTV Icon Gala. Her look was quite simple, but still chic and totally reflective of the time period with the undone buttons, shoulder bag and low slung jeans.

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25. Miss: MTV Video Music Awards 2004

When Hilary stepped out for the 2004 MTV Video Music Awards, she rocked a black strappy tank top paired with short shorts. While this look isn’t the worst, we just wish she wore something a little more elevated and red carpet-worthy considering her level of fame at the time.

Press Association

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24. Hit: Nickelodeon Kids’ Choice Awards 2007

Hilary Duff looked stunning when she stepped out for the 2007 Kids’ Choice Awards wearing this soft yellow jacquard dress. This shape is super flattering on Duff and the color works well with her darker tresses. It’s clear by this outfit that by 2007 Duff had begun to favor a more sophisticated and mature wardrobe.

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23. Miss: Nickelodeon Kids’ Choice Awards 2005

In 2005, Duff stepped out to attend the Nickelodeon Kids’ Choice Awards wearing a white lace top paired with black lace-up pants. The entire look was a little confusing since it was a mix of edgy black accessories with delicate lace and pink velvet.

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22. Hit: Nickelodeon Kids’ Choice Awards 2004

The 2004 Kids’ Choice Awards was a peak year for Hilary Duff! For the occasion, she stepped out wearing a pink cotton dress which she paired with a metallic bag and gold accessories. The true standout feature of this look, however, is the funky pink and yellow ombre shoes that tied everything together flawlessly.

(Photo by Frederick M. Brown/Getty Images)

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21. Miss: Glamour Woman Of The Year Awards 2005

2005 was a huge transitional year for Hilary and her style, which is clear by this elegant look she wore to the 2005 Woman of the Year Awards. Despite the sophisticated color palette and glam makeup, we still don’t think this dress was the most flattering option because of the varying textures and drop-style waist! Luckily it was definitely a step in the right direction towards a more chic and sleek Hollywood wardrobe.

Source: Shutterstock

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20. Hit: Teen Choice Awards 2007

In 2007, Hilary stepped out for the 2007 Teen Choice Awards looking absolutely amazing! This look was the perfect combination of youthful but still sophisticated. It’s hard to go wrong when rocking gold and black, especially when paired with mermaid waves and metallic strappy sandals.

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19. Miss: Crossroads Premiere 2002

In 2002, Hilary stepped out for the premiere of Crossroads wearing a denim jacket paired with matching jeans in a dark wash. While we can definitely appreciate the fact that this outfit was a product of its time, we’re not sure we can ever get on board with lace-up low rise jeans with a metallic waistband.

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18. Hit: Young Hollywood Hot 20 Party 2005

In 2005, Hilary Duff stepped out for the Young Hollywood Hot 20 Party surprising everyone with her fresh, elevated look. This midi-length white dress was super elegant, especially paired with lovely silver accessories. We also love this darker hair shade with bangs on Duff, which made her look much more mature.

(Photo by Kevin Winter/Getty Images)

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17. Miss: World Music Awards 2004

Another unfortunate 2004 fashion misstep of Hilary’s was when she attended the World Music Awards wearing this black sequined dress. The dress itself felt a little messy but especially paired with the knee-high boots and this vinyl record-inspired handbag.

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16. Hit: 18th Birthday Party 2005

Hilary stunned at her 18th birthday party when she stepped out wearing this chic red dress. By 18, she had really simplified her wardrobe and makeup routine which was refreshing to see. We love the sweet pop of pink on her cheeks and the feminine satin headband she accessorized with.

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15. Miss: DVD Exclusive Awards 2005

For a more casual appearance, Hilary attended the DVD Exclusive Awards in 2005 wearing flared jeans and layered knits. While we can certainly appreciate the uniqueness of this knit overpiece she was wearing, we’re not sure it was the most flattering look on her.

©David Longendyke/jpistudios.com

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14. Hit: MTV Video Music Awards 2005

Hilary stole the show when she attended the MTV Video Music Awards in 2005 wearing this gorgeous peach and silver dress. This look definitely gave us all the mermaid vibes, especially with her hair coiffed into a soft side-swept style.

(Photo by Evan Agostini/Getty Images)

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13. Miss: Express Store Opening 2002

During her early days in the spotlight, Hilary was attending many small-scale events and was still trying to nail down her personal style. While we can certainly appreciate the effort behind the coordinating shoulder bag and bucket hat, we’re not sure it worked in her favor, especially when paired with these embellished flare jeans.

(Photo by Sebastian Artz/Getty Images)

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12. Hit: Raise Your Voice Premiere 2004

In 2004, Hilary dazzled on the red carpet rocking this silver sequin dress at the premiere of Raise Your Voice. The soft shape of this dress and icy metallic sequins worked fabulously on her, especially paired with the pop of copper on her heels.

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11. Miss: Kids’ Choice Awards 2003

Hilary, unfortunately, missed the mark with this multi-color look she wore for the Kids’ Choice Awards in 2003. While the hip-hugging skirt and pastel top are definitely quite fun, the lace-up heels detracted from the look as a whole and seemed out of place.

(Photo by Frank Micelotta/Getty Images)

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10. Hit: Teen Choice Awards 2005

Hilary stunned at the 2005 Teen Choice Awards where she stepped out rocking this deep scarlet minidress. This look was a little more risqué than her playful style from earlier years, but it definitely worked in her favor as she matured into a respectable actress outside of Disney.

©Lisa Rose/jpistudios.com

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9. Miss: Toys R Us 2003

In 2003 Hilary attended a Toys R Us event wearing a green tank top paired with printed floral pants. Something about this look screams Lizzie McGuire, but that doesn’t mean it deserves a place outside the show! We’re just not sure that chocolate brown and pistachio green make the most flattering color combination.

(Photo by Evan Agostini/Getty Images)

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8. Hit: A Cinderella Story Premiere 2004

Hilary Duff looked stunning when she stepped out for the premiere of A Cinderella Story in 2004 wearing this asymmetrical miniskirt paired with a long sleeve white blouse. We especially love her freshly streaked locks styled straight and long, which was a refreshing change from her go-to loose curls.

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7. Miss: World Music Awards 2004

Hilary had an unfortunate fashion miss at the 2004 World Music Awards where she stepped out wearing a burgundy sheer top paired with black jeans. The silver stringy necklace and bedazzled belt she opted to accessorize with were definitely quite distracting.

©Jill Johnson/jpistudios.com

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6. Hit: American Music Awards 2003

Hilary looked stunning at the 2003 American Music Awards where she stepped out wearing this asymmetrical peach blouse layered on top of black trousers. We love the feminine, soft quality of this top which paired perfectly with her loose waves and lovely pearl necklace.

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5. Miss: Cheaper By The Dozen 2 Premiere 2005

Unfortunately, we aren’t fans of this multi-color dress that Hilary wore to the premiere of Cheaper By The Dozen 2 in 2005. The look simply had too much going on from the variety of colors to the drop-style shape.

©Jill Johnson/jpistudios.com

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4. Hit: Teen Choice Awards 2003

Hilary looked casual and cute at the 2003 Teen Choice Awards where she rocked a fuzzy pink sweater paired with bootcut jeans and bright yellow shoes. The funky outfit was definitely reflective of the early 2000s but still looked chic and trendy. We especially the cutouts along the sleeves of the top, which added something unique.

©Jill Johnson/jpistudios.com

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3. Miss: MTV Movie Awards 2003

We have to admit we aren’t the biggest fans of this look that Hilary wore to the MTV Movie Awards in 2003. The pinstripe pants and the colorful knit tank didn’t seem to flow together properly to create a cohesive ensemble!

©Lisa Rose/JPI

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2. Hit: Met Gala 2008

Hilary absolutely dazzled at the 2008 Met Gala where she rocked this floor-length silver gown that fit her like a glove and featured intricate beading throughout. By 2008, Hilary had almost completely shed her girl-next-door image and adopted a newfound Hollywood glam look.

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1. Miss: Nickelodeon Kids’ Choice Awards 2002

At one of Hilary’s earliest awards shows, the 2002 Nickelodeon Kids’ Choice Awards, she opted for a long kimono which she paired with flare jeans and chunky wedges. We can definitely appreciate the risk involved with wearing a look this unique and bold, but we’re not sure it was one that was well-rewarded!

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(Photo by Frederick M. Brown/Getty Images)

Olivia Di Pede

Olivia loves all things fashion, beauty, and entertainment. In her free time, she can be found taking yoga classes, reading thriller novels, and styling outfits on Instagram.