We all loved Hilary Duff on Disney’s Lizzie McGuire and we probably emulated her style as much as we could. The early 2000’s was a time of fashion experimentation, and Duff was not afraid to bust out a pair of funky shoes, Juicy Couture dresses, and sweep blue eye shadow all over her lids.
If you wanted to know what style was in the 2000’s, then there is no better example to look at than Hilary Duff. From her starring role as the accident-prone Lizzie McGuire at the age of fourteen to becoming a mother to a six-year-old son, Hilary Duff has matured quite a lot, and it especially shows in her taste in fashion. Her outfits from the 2000’s were indeed questionable, but they made her stand out from the rest. However, now that she’s 31 years old, the actress’ choice of clothing and accessories has changed drastically, and we still love it. The singer has said goodbye to funky pink dresses and said hello to simple pieces that show off her curves.
Take a look at these twenty photos that show Hilary Duff’s evolution of her fashion style and just how much she’s changed from her Lizzie McGuire days.
20. Total Disney Princess
You can’t describe fashion in the early 2000’s without a Tiffany & Co. necklace and small Louis Vuitton pochette. Those two accessories, a long pink dress, and strappy sandals and Hilary Duff’s outfit is complete. This photo was taken in 2001 when the actress was just 14 years old, and it was when she just started out her career as a teen idol, thanks to her starring role as the clumsy Lizzie McGuire.
Hilary Duff even critiqued this particular outfit and described it as “horrific.”
Looking back at old photos of her, Duff said, “I definitely did not have a stylist. No, I think that at that time, I thought it was pretty cool that I had a Tiffany’s necklace and a little Louis Vuitton pochette.”
19. Wearing Clothes That Make Her Look Way Younger
Attending the 16th Annual Nickelodeon Kid’s Choice Awards means dressing up in something fun because it’s really all about having a good time. And plus, no one wants to get slimed wearing designer couture. We get that Hilary was just a teen here, but her outfit washes her out and her hair is literally the same color as the orange carpet. We’re also wondering what she’s holding in that tiny purse on her shoulder that’s also a very questionable fashion accessory.
Hilary Duff was sixteen at this award show, but her outfit makes her look way younger.
18. Matching Belly-Baring Tops At The Kid’s Choice Awards
Hilary and her sister, Haylie Duff, were the ultimate 2000’s girls. At the 2002 Kid’s Choice Awards, the two blonde beauties wore belly-baring tops and chopsticks in their hair. Nothing says early 2000’s than low-rise jeans, tops showing off your midriff, and chopsticks holding up your topknot.
Hilary Duff was the epitome of experimenting with fashion.
17. Too Much Going On Here
In this photo, we’re noticing that Duff still didn’t hire a fashion stylist because there is just so much going on. From the long line cardigan with holes in it, to the American flag printed shirt, and (to top it all off) those hideous flared red pants with embroidery on it,
we have to wonder if she forgot to take a look at herself in the mirror.
Wearing her favorite Tiffany & Co. necklace and Louis Vuitton purse, the starlet couldn’t save any part of this outfit even if she tried. Her pants are just hideous and we hope she burned them when she got older. Her western-styled belt should also be trashed… ASAP.
16. Where Is Her Stylist?
Okay Hilary, not only are we questioning your fashion sense here, but we’re also wondering why Frankie Muniz is wrapped around your arm. Duff sure loves her small purses, and this one tops them all with its glitter and frills. Her purple jacket with fur trim is a fashion don’t, and even though the 2000’s were all about funky style, this jacket is hideous. Let’s talk about her shoes, though. Are those alligator cowboy boots? We hope that for Hilary’s sake, she got rid of them—that purple coat and those low-cut jeans. If you’re wondering what Muniz is doing around her arm, we’re taking a guess that they’re together for their 2003 film Agent Cody Banks.
15. Are Those Butterfly Clips In Her Hair?
Hilary Duff was a presenter at the 29th International Emmy Awards in New York City on November 19, 2001 and was just beginning to gain stardom at the very young age of fourteen years old. The actress definitely knew all the trends back then, but this one-piece with ruffles all over is just in bad taste. While it does a good job at showing off her slim figure, it must be a pain in the behind to take this number off to use the restroom. And are those butterfly clips in her hair? Are you overcome with nostalgia yet?
14. All Denim Everything
This all-jean look screams iconic fashion moment of the 2000’s. Girls were probably so envious at this starlet while she walked the red carpet in this matching jean set. All-denim everything was a huge fashion trend no matter what wash or color.
Hilary looked like the definition of “cool girl” and knew how to rock this look,
even if we’re hoping she tossed it in the trash a few years later. Hilary looks like she’s trying to go for a more sexier look here, trying to get rid of her Disney persona by showing off her midriff and wearing very, very low-rise jeans. She definitely caught our attention with this look, and sadly, it’s not for the right reasons.
13. The Cool Girl On The Red Carpet
The “What Dreams Are Made Of” singer was really into wearing low-rise pants and showing off her toned midriff during the 2000’s. While they were great for flaunting your midriff, they also made bending over difficult.
Hilary Duff experimented with her fashion and wasn’t afraid to mix and match colors and patterns,
even though she might have regretted some of her fashion choices today. This shirt and pants combo might have been all the rage, but we don’t think Hilary would be caught dead in this fashion choice now.
12. Von Dutch Red-Hot Bell-Bottoms
Remember how much we loved watching MTV’s Total Request Live and tuned in every day to see our favorite celebrities get interviewed and watch which star’s video made it to number one? TRL began in 1998 and lasted until 2008 (until its reincarnation in 2017 that isn’t as popular), and not only did we love to watch the awkward interviews and hilarious moments, but we also loved to see the fashion. In 2003, Hilary Duff showed up to the show in this number, rocking a pair of Von Dutch red-hot bell-bottoms that were probably the coolest pants ever back in the early 2000’s. This was definitely not the Lizzie McGuire we knew when she first came into the spotlight.
11. “Icy Pink Teenage Dreams”
Fashion at the Grammy Awards has always been shocking, over-the-top, and sometimes even outrageous. It’s one award show where celebrities can wear whatever they want, showcase their individual style and make a statement on the red carpet. At the 2004 Grammy Awards, Hilary brought her older sister, Haylie Duff,
and both of them looked like a pair of pink washed-out Barbies.
An article for E! News called the sisters “icy pink teenage dreams,” and they couldn’t have been more correct. These dresses didn’t show off any of the girls’ personal fashion style and weren’t the jaw-dropping outfits we expect at the Grammy Awards.
10. Trying To Find Her Personal Style
In the same year, Hilary Duff did a 180-degree turn on us when she attended the 2004 MTV Video Music Awards in this all-black ensemble, and we were still confused what exactly her personal style was. From wearing a glittery pink dress at the Grammy Awards to changing up her look completely at the VMA’s,
wearing an off-the-shoulder tank top, black shorts, and way too much jewelry,
9. Getting Rid Of Her Disney Days
In the 2000’s, Hilary continued to change up her style, and it looked like she finally said goodbye to her sweet Disney persona. She dyed her hair darker, got a tan, and was wearing a little more revealing outfits like these very short shorts with fishnet stockings. Statement jewelry was another big thing, and Hilary Duff knew how to rock every single bracelet she owned. However, she still appeared to layer random pieces of clothing together that didn’t do her any justice. And certainly did not compliment each other well.
8. Missing Her Blond Hair
Still rocking the brunette hair color, Hilary Duff appeared at the 2007 MuchMusic Awards red carpet in Toronto, Canada in this dress that
almost looks like she wrapped a towel around herself and called it fashion.
We also don’t really understand the gigantic black rectangle on the dress, which appears to be sewed on, giving us the impression that maybe the dress was too risky for her to wear, but she still wanted to wear it and had someone add the black fabric to it. At least her hair looks good, but we kind of like the blond better on her.
7. Finding Clothes That Fit Her Curvy Figure
We’re starting to really see Hilary Duff’s personal style now, and it’s not because she decided to dye her hair this blue-green color. The actress finally said “so long” to chopsticks in her hair and Tiffany & Co. necklaces and went for a more sleek and sexier look that we can’t help but love.
Duff has great curves, and she works them well in this red dress by Mason by Michelle Mason that goes for $230
and matching red lipstick. But why in the world would she dye her statement blond hair for green tresses? Duff admitted that when she was in Mexico with her son, Luca, she stared at the ocean and said, “I want that on my head.” And poof, it happened.
6. Looking Fantastic In Simple Pieces
Hilary Duff may still experiment with fashion but still keeping it simple (like she does in the above photo) looks just as good on her. Wearing a white t-shirt, black Mother Denim jeans for $196, a nude heel, and a Raquel Allegra satin pink coat for $795,
Duff makes these must-have wardrobe pieces look high fashion.
And let’s mention how spot on her makeup looks here too. She said goodbye to that tacky blue eye shadow we all wore back in the early 2000’s and swapped it for a very sexy, smoky eye shadow. This is definitely one of our favorite looks on Hilary.
5. Breaking The Internet
Can we talk about how amazing Hilary Duff’s body is in this photo? Where has she been hiding it all these years? Stepping out in this tight pink dress, the actress definitely had heads turning and for all the right reasons. This is one of Duff’s best looks, pairing her skin-hugging dress with a pair of sexy stilettos and blue cross body bag.
This photo of Hilary was actually trending worldwide on social media
because everyone couldn’t help but drool over her toned figure. She might have even knocked Kim Kardashian off her throne and broke the Internet.
4. Knows How To Put Together Pieces Effortlessly
Again, here is Hilary showing us that she has great personal style. She’s out on the town wearing a simple white t-shirt, motorcycle jacket, black pants, and nude boots while holding a big grey scarf to complete her trendy look. We love that the Younger star knows how to put together looks so effortlessly.
Any girl would want to steal this look because it’s so chic yet anyone can pull it off.
3. We Love Her Chic Style
Hilary Duff has been killing the fashion game, and we love everything she’s been spotted wearing (as of late, obviously). We love how the star rocked a slouchy sweater with ripped jeans, green heels, and bandana wrapped around her neck. Her look is so simple yet it looks very fashionable on the beautiful star. Good thing she dumped those low-ride jeans for a more chic high-waisted pair and gave up her pounds of necklaces for a simple handkerchief scarf.
2. Mixes And Matches Her Clothing Perfectly
Hello, glam! Hilary Duff’s fashion evolution has drastically changed since she started out and became a Disney teen idol with her role on Lizzie McGuire. Don’t get us wrong, she still loves her patterns and colors, but this time, she’s doing it right. Her striped shirt and burgundy mini skirt that shows off her killer legs is sexy and playful. We love how she’s still experimenting with style and mixes and matches pieces that are super flattering on her. And those shoes, where can we get those Hilary?
1. Has Heads Turning With Her Outfits
From girly pink dresses to designer must-haves,
Hilary Duff’s fashion has drastically evolved from her days filming as Lizzie McGuire.
Do we have to tell you how amazing she looks in this white-and-navy-blue dress? We don’t think so. The actress has really embraced her sense of style, and we can truly see her love of fashion. She continues to impress everyone with her wardrobe, whether she’s wearing a simple t-shirt and jean combo or strutting her stuff in a skintight dress and heels. Still, you have to admire her unique style and love for fashion experimentation as Disney’s Lizzie McGuire.
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