Hilary Duff’s early 2000s style evolution unfolded in the spotlight, not just through red carpet appearances, but also during her high-profile relationship with Good Charlotte frontman Joel Madden.
On February 9, 2006, Hilary Duff stepped out at Olympus Fashion Week in New York City wearing a printed Zac Posen dress, brown leather boots, a blush pink coat, and carrying a brown Fendi Spy bag, while Joel Madden kept it casual in black with a pinstriped blazer (Credit: Dara Kushner / INFGoff)
In July 2004, when Duff was just 16 and Madden was 25, the duo began dating—just a year after she ended her relationship with fellow teen star Aaron Carter. As their controversial romance drew media attention, so did Duff’s growing fashion maturity, transitioning from teen pop princess to edgy, trend-conscious young star.
Hilary Duff stuns in a sheer, sequin-embellished nude dress with coral piping while posing with Joel Madden—dressed in a pinstriped black suit—at the 2005 MTV Video Music Awards (Credit: WENN / Nikki Nelson / David Livingston)
Red Carpet Style & Private Romance: Hilary Duff’s Early 2000s Fashion During Her Joel Madden Era
Hilary Duff dated Good Charlotte rocker Joel Madden from 16 to 19. Though she has kept details of their relationship private, she implied in an April 2015 issue of Cosmopolitan magazine that he was the first person she had sex with.
“I had a 26-year-old boyfriend,” Duff said in the interview. “So everyone can make their own assumptions about what I was doing.”
“I’ve enjoyed myself. I think everyone should have something where you know it’s not exactly what you’re looking for but you just have a wicked good time. That was freeing for me and a bit of an awakening. It’s fun to have a secret.”
Hilary Duff stuns in a delicate white lace dress with floral embroidery, paired with dangling earrings, while Joel Madden sports a black velvet blazer and LA cap during their high-profile relationship from 2004 to 2006 (Credit: Darrell Graham / Startraksphoto)
Looking Back: Duff and Madden’s Breakup and the Style Legacy of Their Relationship
Joel Madden, born on March 11, 1979, in Waldorf, Maryland, is nine years older than Hilary Duff, born on September 28, 1987, in Houston, Texas. They broke up in November 2006.
“I kind of ignored it and tried to just continue to live my life,” Madden told People about their breakup in March 2007.
“People can say or think whatever they want …so in my reality, it’s kind of irrelevant. I’m always the kind of person that does the right thing and keeps my side of the street clean.”
Hilary Duff celebrates her 18th birthday in a glamorous strapless red satin dress with a pink satin headband and sparkling diamond jewelry, joined by Joel Madden in a dark embroidered blazer and fedora (Credit: WENN / Nikki Nelson / David Livingston)
After her highly publicized relationship with Joel Madden and eventual split, Hilary Duff shifted her focus to her career and personal growth.
In early 2016, Hilary Duff experienced a more personal kind of heartbreak that unfolded quietly behind the scenes. Despite the emotional weight, she returned to the spotlight gracefully, channeling her strength into a polished appearance that reaffirmed her signature style.
Stepping Out in Style: Hilary Duff Returns to the Spotlight After Personal Loss
Hilary Duff was seen in January 2016 putting on a brave face while arriving at AOL Build in New York City following the passing of her French bulldog, Beau.
The then-28-year-old actress was “shattered in a million pieces” over the passing of her dog. Still, she continued her promotional duties for the second season of her comedy-drama TV series, “Younger.”
Hilary Duff expressed her heartbreak on Instagram over the passing of her French bulldog, Beau, posted on January 12, 2016 (Credit: Hilary Duff’s Instagram)
In January 2016, while promoting the latest season of Younger, the Lizzie McGuire actress put her curves on display in a sexy fitted red sleeveless dress by Alexander Wang.
Hilary Duff wears her blonde hair down as she arrives at AOL Build in New York City on January 13, 2016 (Credit: WENN / Nikki Nelson / David Livingston)
It featured a sexy zip detail on her stomach that goes around the back and down on the left side and a thigh-high slit that showed off her toned leg.
Hilary Duff turns heads in a bold red Alexander Wang dress with a thigh-high slit, layered under a white Camilla and Marc trench coat, and finishes the look with nude Brian Atwood “Tamara” sandals that elongate her petite 5-foot-1 frame
For added glamour—and to elongate her petite 5-foot-1 (154.9 cm) frame—she draped a white Camilla and Marc trench coat over her shoulders and slipped into nude heels, a classic height trick that creates a streamlined effect and visually lengthens the legs.
Hilary Duff finishes her AOL Build ensemble with a white trench coat from Camilla and Marc (Credit: WENN / Nikki Nelson / David Livingston)
She wore her short blonde locks in tousled waves, complemented by smoky eye shadow and a slick of vampy red lipstick.
Hilary Duff’s nude Brian Atwood “Tamara” sandals feature sleek crisscross ankle straps and a slim stiletto heel, creating a leg-lengthening effect perfect for her petite frame
Hilary wore the “Tamara” sandals from Brian Atwood’s Spring 2014 collection. They are made of nude patent leather, feature crisscross ankle straps, and have about 3.5-inch heels.
Hilary Duff’s nude Brian Atwood “Tamara” sandals showcase her polished pedicure, with neatly groomed toes adding a touch of elegance to the strappy, leg-lengthening design
Stepping Out in Style: Hilary Duff’s Most Memorable Shoe Moments
Hilary Duff has consistently showcased her impeccable fashion sense, particularly through her choice of footwear. Here are some of her most memorable shoe moments:
Hilary Duff Celebrates 25th Birthday in Red Christian Louboutin Pumps
- Event: 25th Birthday Celebration in Beverly Hills
- Outfit: Hilary paired a chic printed blouse with dark cropped skinny jeans.
- Footwear: She completed her look with bold red Christian Louboutin “Bianca” pumps, adding a pop of color to her ensemble.
- Read more: Hilary Duff Shines in Christian Louboutin Heels for Her 25th Birthday
Hilary Duff Promotes ‘Younger’ in Gucci ‘Angel’ Pumps
- Event: AOL BUILD Series Appearance in New York City
- Outfit: Hilary wore a blush-colored one-sleeved mini dress, showcasing her toned physique.
- Footwear: She elevated her look with beige Gucci “Angel” platform pumps, adding sophistication to her ensemble.
- See more: Hilary Duff Teases New ‘Younger’ Season in Gucci ‘Angel’ Pumps
Hilary Duff’s Casual Chic with Schutz’s ‘Gilberta’ Pumps
- Event: Lunch Date in Los Angeles
- Outfit: Hilary kept it casual with a short-sleeved Topshop shirt and AMO “Babe” denim jeans.
- Footwear: Her moss green Schutz “Gilberta” pumps added a touch of elegance and demonstrated her versatile style.
- Discover more: Hilary Duff’s Schutz Pumps
Hilary Duff’s Edgy Look with Charlotte Olympia ‘Dolly’ Pumps
- Event: Debut Novel Launch at Hotel Costes in Paris
- Outfit: Hilary showcased an edgy ensemble with a leather jacket, patterned scarf, and skinny jeans.
- Footwear: She completed her look with pink Charlotte Olympia “Dolly” canvas pumps, adding a feminine touch.
- Explore her style: Hilary Duff’s Elixir of Style: Pink Pumps and a Debut Novel Launch
Hilary Duff’s Sophisticated Ensemble with Christian Louboutin ‘So Kate’ Pumps
- Event: ‘The Elephant Man’ Broadway Opening Night in New York City
- Outfit: Hilary donned a camel coat over a white top and leather skirt, exuding sophistication.
- Footwear: She paired her outfit with black suede Christian Louboutin “So Kate” pumps, adding elegance to her look.
- See her look: How Hilary Duff Wears Camel Coat With Leather Skirt and High Heels
These moments highlight Hilary Duff’s ability to seamlessly integrate stylish footwear into her outfits, solidifying her status as a fashion icon.