Hilary Duff Has Had the Most Epic Style Evolution

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In 2001, Hilary Duff first won our hearts as the daydreaming Lizzie McGuire. Now, two decades later, Hilary continues to impress us with her role as Sophie on Hulu’s How I Met Your Father.

So, in honor of Miss Duff, let’s take a stroll down memory lane as we watch our favorite early aughts icon go from cutesy teen to full-blown fashionista.

‘Remember the Titan’s Premiere, September 2000

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Just a few months before Lizzie McGuire premiered on Disney and Hilary Duff hit up the red carpet for the premiere of Remember the Titans rocking classic Lizzie hair and some hot pink pants.

Grand Opening of ONE SEVEN Teen Dance Club, November 2001

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One season into Lizzie McGuire and Hilary is rocking her signature pink color at the opening of ONE SEVEN teen dance club. This would be around the time that she started dating fellow teen idol Aaron Carter.

E!’s Sizzling 16 Awards, January 2002

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Wow, Hilary is *rocking* that faux fur-trim jacket! Hilary Duff switched from her signature pink for purple for the E! Sizzling 16 Awards red carpet.

‘Shanghai Knights’ Premiere, February 2003

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At the Shanghai Knights premiere, Hilary Duff gave us quintessential early aughts fashion with a pink baby tee, shoulder bag, and choker. This was a huge year for Hil — it was the same year her hit album Metamorphosis came out as well as her films Cheaper By the Dozen and Agent Cody Banks.

‘A Cinderella Story’ World Premiere, July 2004

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Nothing says 2004 like a low-rise mini skirt! Hilary rocked this look for the premiere of her iconic teen romcom film A Cinderella Story, which co-starred Chad Michael Murray.

Teen Choice Awards, August 2005

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Ah, 2005! This was the start of Hilary’s heavy eyeliner era when she decided it was time to transition from Disney princess to sex kitten. This was also the era when Hilary was dating Good Charlotte member Joel Madden.

GLAAD Awards, March 2007

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Remember when Hilary Duff went brunette? Yeah, we’ve tried to forget too.

MET Gala, May 2008

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Hilary looked super pretty in her silver sequin Elie Saab gown at the 2008 MET Gala! You gotta love it.

1st Annual Children Mending Hearts Style Sunday, June 2013

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The knit maxi dress and chunky belt are giving us *major* flashbacks (and not in a good way). That said, Hilary’s makeup and hair look a lot more grown up as she transitions again from her post-Disney rebellious era to the current Hilary we know and love today.

Teen Choice Awards, August 2014

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We are totally loving Hilary’s short mom haircut! At this point, Hilary has a two-year-old at home, a hubbie, and is getting ready to start her gig on Younger.

Spotted in NYC, January 2016

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Hilary looks great in this red midi dress and white overcoat! Her style is becoming more and more honed as she grows into her own as an adult.

Love Leo Rescue 2nd Annual Cocktails For a Cause, November 2019

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Hilary Duff looks absolutely stunning in this green suit! Things have changed so much for Hilary by this point  — not only is she a mom of two, but she has a hit show Younger on the air and is getting ready to marry her husband Matthew Koma.

Baby2Baby 10-Year Gala, November 2021

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Hilary looks amazing in this Osman red sequin gown paired with Rahamoniv jewels at the Baby2Bay 10-year gala. Keep doing you, boo!

Watch What Happens Live! With Andy Cohen, January 2023

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Talk about a glow-up! We can’t believe how much Hilary Duff has grown over the years! Hilary Duff has seriously never looked better. Dare we say 2023 is officially the year of Hilary?


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Lena Finkel
Lena Finkel is the Editor and Founder of Femestella. Prior to starting Femestella, she worked at People, InStyle, Tiger Beat, and Sesame Workshop (aka Sesame Street). She loves all things Real Housewives and Vanderpump Rules. When she's not busy binge-watching TV, you can find her hanging out with her tuxedo cat Tom.