Then & Now: 20 Photos Of Hilary Duff's Evolution

An adorable pre-teen dealing with life, boys, and friends (and sometimes she appeared as a fun cartoon). An aspiring singer getting over a personal tragedy. A book editor living in NYC and wearing super trendy clothing.

These are just a handful of the roles that Hilary Duff has had over the years. She starred on the sweet and popular show Lizzie McGuire from 2001 until 2004, she was in the 2004 movie Raise Your Voice, and today she stars on the TV series Younger.

Hilary has also released several albums and songs, but today, the actress and singer is most known for being a mom of two. She has a seven-year-old son named Luca and a six-month-old daughter named Banks.

Whenever someone has been in the spotlight for such a long period of time, it's always cool to see how they have evolved in that time. Do they still look the same in terms of their makeup choices, hairstyles, hair color, and how they dress? Or have they truly grown up to the point where we can't even recognize their former self?

Let's take a look at how much Hilary Duff has changed over the years. Here are 20 photos of the celeb's evolution.

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20 Then: Remember When Hilary Duff And Aaron Carter Were A Thing?! This Was Back In 2003

via Us Weekly

This photo is from back in 2003 when Hilary Duff and Aaron Carter were a couple. We can probably remember that they were in a relationship... because there was a ton of drama between Hilary, Aaron, and Lindsay Lohan.

As Buzzfeed says, Hilary and Aaron were a thing from 2001 until 2003. The website quotes Aaron Carter who said, "I started dating Hilary [Duff] on my 13th birthday. I was dating her for like a year and a half and then I just got a little bored so I went and I started getting to know Lindsay [Lohan], dating Lindsay."

Um, whoa... But Hilary and Aaron look so happy in this photo, right?! We love her sparkly dress and curly hair.

19 Now: The 'Younger' Actress Goes For Comfort These Days But Still Looks Chic, And Here She's Getting Takeout (Just Like We Like To Do)

via Us Weekly

Here's a more recent picture of Hilary Duff, and we can she totally goes for comfort these days. We love her cool sweatshirt with what looks like Kurt Cobain's face on it, her purple leggings, and her shiny silver sneakers. We also enjoy the fact that Hilary's carrying some takeout bags.

When it comes to how her style has been altered since having kids, Hilary Duff wrote in a December 2018 social media caption, "Don't get too get fancy very often these days. So I took a selfie to remember my old self ... however the real thing to remember is that this tiny baby and spit up and sweat pants and not leaving the house is temporary and will actually be a phase that is gone too quickly."

18 Then: The Star Had A Cheesy Grin And A Very Early 2000s Outfit (And This Was 2001)

via HuffPost

Hilary Duff has quite the cheesy grin in this photo, and we get it: she was so successful as a pre-teen so she must have been enjoying doing what she loved. When she was in her early teen years, she was cast in the main role on Lizzie McGuire, and she was in a lot of movies around that time period. Remember when she and Chad Michael Murray starred in A Cinderella Story in 2004? Or when she was in Cheaper By The Dozen in 2003? Those were some early 2000s classics.

Hilary's outfit is very early 2000s as well. Chances are, we probably wore a lot of outfits like this one ourselves, and what pre-teen girl wouldn't want a cute bright pink top?

17 Now: We Love Hilary And Son Luca's Smiling Faces In This Pic (And We Want Her Beige Coat)

via Us Weekly

These days, Hilary is a busy mother, but she's not one to slack when it comes to personal style. We really love the beige coat that she's wearing in this photo of her and her son, Luca, and we can't get enough of their grins. They look so pleased to be hanging out.

When she was interviewed by Parents magazine, Hilary said about being a mom, "The love you have for your child is so much greater than any challenge you'll face as a parent, and that's what helps you through." That totally brings tears to our eyes and we can tell that she's amazing at being a mother.

16 Then: Hilary Went Through A Blue Hair Phase, And We Love This Pic Of The Actress In 2015

via Pinterest

Of course, blue hair isn't exactly a look that everyone would try out. And some of us might be fans of Hilary Duff and would still say that we don't really like this hair color.

But the rest of us think that she was super brave for trying this out, and we give her props for that. Even if we would never dye our own hair blue (or any wild shade), we have to admit that Hilary rocked it. She made blue hair chic, and in this photo from 2015, she's wearing an understated jacket and top and she really makes the look work.

We wonder if she'll return to blue hair anytime soon?!

15 Now: We Love Seeing The Celeb With Her Beau Matthew Koma, And Here She Was Pregnant With Their Baby Girl

via Us Weekly

Fans of Hilary Duff rejoiced when she announced that she was pregnant with her second child, and now her baby girl Banks is six months old. This is a great picture of Hilary with her partner, Matthew Koma, and what we love about it most of all is her super casual outfit. She's got a simple white tank top on with a blue shirt tied around her waist, cute sneakers, and peach-colored leggings. We have a feeling that she lives in sneakers and leggings which, honestly, same.

Besides loving her acting roles, songs, and her style, fans also appreciate that Hilary talks about being a mother and will say that she hasn't gotten tons of sleep or that she's had some hard moments.

14 Then: Hilary Was Rocking A Girly Pink Look Back In 2001, Looking Much 'Younger'

via Life & Style

If anyone was a fan of Hilary Duff back in the day, they remember her on Lizzie McGuire and in some sweet and innocent movies, and they also remember her looking like she did back when this photo was taken.

It's a girly look and every detail reminds us that she was a pre-teen in this picture, from the pink ruffled top to the silver heart locket.

As Hilary told Popsugar about Lizzie McGuire, "Girls really needed someone like that to look up to. And that is really who I was at that time in my life, too. I'm really appreciative for that role, and I loved her, too. She was me."

13 Now: Hilary's A Mama For The Second Time And Has A Sweet Baby Girl Named Banks (And Looks So Chill)

via Got Celeb

Okay, by now we have total proof that Hilary Duff lives in comfy sneakers, so if we're ever feeling insecure about not wanting to go for heels or fancy shoes all the time, we can just think about Hilary. Phew.

Besides her comfortable shoes, we can definitely appreciate the rest of her outfit in this fairly recent photo. Hilary's wearing a cool t-shirt, two-toned jeans, and of course, the most important part of this photo is that she's got her baby girl Banks in a carrier. Cool and stylish mom alert. We can also relate to the fact that she's carrying her phone and two types of beverages. We all do that, don't we?!

12 Then: Hilary Even Went For A Pretty In Pink Hairstyle In 2016

via Pinterest and Beauty Launchpad

Since Hilary Duff isn't one to back away from changing her hair color, we could have guessed that it was only a matter of time before she would dye her hair something other than blue. In 2016, she went for a pink look, and we have to say that it's so great. The fact that she was wearing her hair in a bob made it even better.

According to InStyle, Hilary said, "Toward the end of filming Younger, I knew I wanted to do something fun with my hair." She continued, "When I’m not working, dyeing my hair is a fun thing for me to do. I had greenish-blue last year, and had a lot of fun with it."

11 Now: The Actress Has Totally Mastered The Stylish Yet Casual Vibes In 2019

via Celeb Vegas

In this recent photo taken of the star, Hilary Duff totally looks like a busy mom: she's on the phone, carrying a cup of coffee, and has a big purse on her shoulder.

If we grew up in the '90s and were a big fan of Hilary when she was in a lot of movies in the early 2000s, we can appreciate the evolution that she has had. After all, now she's 31 years old and a mom of two.

And we've grown, too. Would we put on this comfortable sweater and ripped jeans and booties? Absolutely. Hilary has some serious style in 2019.

10 Then: Hilary Wore This Look For Her Music Video For 'Wake Up' (And We Don't Get The Long Scarf And Tank Top Combo)

via iMDB

This photo is a great reminder that Hilary Duff is also a singer. In fact, she has five albums: 2002's Santa Claus Lane, 2003's Metamorphosis, 2004's Hilary Duff, 2007's Dignity, and then Breathe In, Breathe Out in 2015.

Hilary had a single called "Wake Up" from her 2005 album called Most Wanted. The album featured a bunch of her most popular songs, including this new one.

While some of us might remember this song (and thought that it was super fun and catchy), we might not be super sure about the long scarf and tank top combination that she's wearing. It's not the best look, but hey, we all made some early to mid-2002s style choices like this.

9 Now: We're Loving The New Hilary In This Comfy Sweats Look


There are many celebrities who we would say we could take style lessons from. The Kardashian-Jenner clan would definitely be up there, and we would say that Hilary can show us a ton about looking elegant while wearing clothes that are still comfortable. It's not always easy to do that. We love this look: a chic sweatshirt and comfy pants plus little booties.

Hilary makes sure that her son Luca looks sharp as well: according to Yahoo! Style, Hilary said, “He has these blue tennis shoes, and I can’t get them off his feet. I bought him the exact same pair in a different color combination, so people at school didn’t think the poor kid only had one pair of shoes, and he refuses to wear them because they’re not blue.”

8 Then: 2002-Era Hilary Duff Was In A Definite Purple Period... And The Outfit Is Awkward

via HuffPost

Everyone looks at throwback photos of themselves and would never choose the same outfit again, but hindsight is 20/20, as they say. We're older now and we dress differently in 2019 than we did in 2002.

Hilary was definitely rocking a very purple look in this 2002 photo, and there are a lot of things going on here. Shes' got flared jeans that look way too long since they go over her shoes (and they also look like they're ripped at the bottom). She's wearing one of those 2000s belts that has a bunch of chains, a sheer mauve top, and a fluffy purple coat that is probably fake fur. It's... a lot.

7 Now: It's All About Family Time Now, And Here The Happy Parents Are

via Page Six

Here's another recent picture of Hilary Duff that shows her evolution through the years. She's holding her baby girl, which is definitely a sign of how things have changed, and we're giving her props once again for her cool outfit.

Sure, she's wearing sandals and jeans, which are fairly simple and not the most out there in terms of personal style, but she's also wearing a really chic navy blue shirt. It kind of looks like a pajama top, which makes it even more fashionable since that's a trend in itself. Hilary and her beau, Matthew Koma, look really stylish together.

6 Then: Hilary Even Went Grey For A Little While (And We Have Mixed Feelings)

via Pinterest

After blue hair, we might have thought that Hilary Duff would have returned back to blonde hair. Many fans would probably say that they're used to seeing her as a blonde.

In 2015, she went for grey hair, and this is a photo from that time. We have mixed feelings about it because while she always has amazing and beautiful hair, grey is a tough color.

People quoted something really funny that the star shared about her son: she said, “Luca is very particular about how he likes my hair. There’s absolutely no buns on my head, no ponytails. I’ll have a ponytail and he’s like, ‘Um, hair down, mom. Hair down, please.’ At least he knows what he likes."

5 Now: Hilary's A Boy Mom And Always Loves Hanging Out With Her Little Guy

via Pinterest and Daily Mail

It's really sweet to see a favorite celebrity become a mother and experience everything that comes along with it. Okay, we can't exactly watch them experience everything since we don't know them super well... but we can at least see cool photos like these two.

In the photo on the left, Hilary's wearing really pretty light blue pants and a fun pattern on her t-shirt, and on the right, she's wearing an equally comfortable outfit since she's got a t-shirt, pants, and grey sweater on. We also have to point out that Hilary's carrying really cute purses in both pictures and Luca's also rocking some fun patterns. What a cute little guy.

4 Then: Once Upon A Time, Hilary Was A Pop Singer

via Pinterest and E!

Talk about the evolution of Hilary Duff. These two photos give us a glimpse into her life as a pop star. While she hasn't had an album out since 2015's Breathe In, Breathe Out, she definitely spent a lot of time coming out with new music and performing.

In a 2016 interview with Aol.com, Hilary said about music, "I haven't been dabbling yet, but I think I will. It's so hard because I feel like I get pressured into it by my fans or people that ask. They're like, 'What's going on?!' And I'm like, 'I don't know!'" We're totally going to rejoice when we do get that new music.

3 Now: Hilary Duff's Light Blonde Hair Just Might Be Her Best Look Yet

via CelebMafia

Today, we're much more likely to see Hilary Duff with light blonde hair instead of blue or pink, and we really love it. It honestly seems like her best look yet because she looks awesome.

This is definitely a rare sighting of the star wearing boots with a bit of a heel on them. As Yahoo! Style quoted her as saying, “I wear flats every day of my life now. I never thought I’d be that person. It happened slowly but all of a sudden all I was wearing were little heeled booties, and now I’m just like straight flats and it’s awesome. I wear high heeled shoes for minimum 14 hours a day when I’m on set, which is actually really hurting my feet. Gotta give this old girl a break!”

2 Then: Hilary Was Filming 'Younger' In NYC In 2016 (And It's Her Best Role Yet... Besides Being A Mom Of Course)

via Pinterest

Hilary Duff told Yahoo! Style that her character on Younger, Kelsey Peters, wears way different clothing than she does IRL. She said, “I love what I wear on the show but it’s a lot more fussy than what I wear in real life. Kelsey wears brighter colors, more prints, and tighter clothes."

This is a photo from back in 2016 when Hilary was filming the show. We can see that her character's clothing isn't exactly what we've seen her wear in the other photos on this list, right down to the bright blue high heels. She looks great, though, of course, and fans love her on the show.

1 Now: She's Got Mom Vibes With A Bob Haircut, And We Think She Looks Amazing

via People

Many moms go for a bob hairstyle because it's pretty easy to take care of. Thankfully, bobs are always in, especially when someone looks as trendy with this hairstyle as Hilary Duff does in this recent picture.

We think that Hilary Duff looks amazing and we would totally support her keeping this hairstyle around for a bit longer. But, of course, she's always going to look stylish, no matter what she decides.

These 20 photos gave us an interesting look at the evolution of Hilary Duff over the years, and we love seeing how much she has changed. One thing that hasn't changed, though: we're still super big fans.

Sources: Buzzfeed, Eonline, Parents, InStyle, People, Yahoo Style

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