WWW20: Mandy Moore, From Teen Pop Icon to Award-Winning Actress

Watch On This month, Who What Wear is celebrating its 20th anniversary. To commemorate two decades of spotlighting tastemakers and style leaders, we’re dedicating October to guests who have shaped the fashion industry and cultural conversation since Who What Wear’s inception. This week’s guest is Mandy Moore!

Moore has been in the spotlight for over 20 years, from releasing her hit 1999 song “Candy” to starring in A Walk to Remember and This Is Us. For the latest episode of The Who What Wear Podcast, Moore sat down with Hillary Kerr to reflect on getting her start as a teen pop star, her outstanding acting career, and her most memorable fashion moments from the past 20 years. Plus, she shares everything you need to know about her highly anticipated new show, The Land.

To read excerpts from their conversation, scroll below.

Talk to me about the story of how you were discovered because it is wild.

So I was just like a dorky musical theater kid growing up in the suburbs of Orlando, Florida, with dreams of being on Broadway and also simultaneously falling in love with singing the national anthem at different sporting events, which is a crazy thing.

I remember seeing a young woman my age sing the national anthem at an Orlando Magic basketball game, and I was like, “You can do that?” It was such a huge light-bulb moment for me.

Cut to sending in a tape of me singing, getting chosen to sing, then becoming sort of the de facto national anthem girl throughout Orlando for all these different sporting events. [Then I was] kind of discovered from singing the national anthem, offered the opportunity to start recording music at a proper recording studio, which then led to a gentleman who worked for FedEx, who had a friendship with someone that was able to send it to someone else, to someone else, to someone else.

Eventually, [he] sent this unfinished demo of mine to one of the heads of A&R at Epic Records. I wasn’t even 15. I was 14, and this guy flew from New York to Orlando, and I sang for him and had this quasi audition. And he heard something he liked, and I signed this record deal in like the winter of 1998, and started making my first record in ’99, which then led to opening up for Nsync and the Backstreet Boys, and then that ball was rolling, and here we are in 2026.

Do you remember what was on that demo? Do you remember like what you were thinking about when you were creating it?

Some of the music was stuff that eventually did end up making it on my first album.

Yeah. So these two writers that heard me sing the national anthem at an ice hockey game were songwriters and producers, and they ended up working on the majority of my first album. So a lot of those songs that we were working on back then, not “Candy” or anything, but some of the other songs ended up being on my first record.

It’s strange to think back to that time because I was 14. I had maybe kissed a boy in a game of truth or dare. Like I had never French kissed a boy. So I’m singing these songs that I truly have no point of reference for.

One of the things that I love about your career is a the longevity but also just the fact that you have done so many different things, and I feel like that diversity of experience is wonderful, and it speaks to your talent. So how did you start with the acting world?

I think because I grew up doing theater, it was always in the back of my mind. Like if any door opens for me, whether it’s like Broadway or music or what, I want to try a little bit of everything.

I knew that if I could tiptoe into the acting world, it was something I wanted to try. And I took a bunch of meetings, and then, the very first thing that I feel like I properly auditioned for was The Princess Diaries. And I just remember going to Toluca Lake and meeting Garry Marshall at his theater, and I was like, “Oh, he’s like someone’s grandpa.” He was just so friendly and funny and warm. And I was like, “I just want to hang out with him. He seems like he’s going to be a lot of fun and like so goofy.”

And it was. It was the best experience, and it kind of felt like being at summer camp because it was a movie with a ton of other young people my age, and it just felt fun.

Let’s talk about that [Princess Diaries] premiere look. A suit, an acid-washed denim suit.

It was denim, and it was low-rise too. A pale denim suit with a black tank top. It was a strange choice. And white sneaker pumps with a big thick stacked heel. It was a choice.

It was the era for sure. Like I was definitely within my rights, fashion-wise. But would I choose that now? Absolutely not. Maybe a darker denim suit.

It wasn’t my movie. I was just a part in the fabric of this movie. It was Annie’s movie and, you know, Julie Andrews’s. So I was happy to be there to support. Proud to be a part of it. So it felt to me like it was casual while still sort of taking myself seriously, maybe a little bit more than a musician-posing-as-an-actor kind of thing.

Talk to me about A Walk to Remember and what it was like going from a supporting role to a lead role.

It was a lot of weight. The dark hair really helped. I know it sounds so dumb, but the amount of questions I got during that time about like, “Did I feel like I was taking myself seriously now?” I mean, just like going from blonde to brunette, I’m like, “What?” That press tour was all about my hair color.

I was never as famous as Madonna or Britney Spears or other musicians that were transitioning to acting roles, where I felt like they were maybe at more of a disadvantage because it was harder for people to separate them from their public persona, right? Like you knew everything about Britney or Madonna or Christina Aguilera or whomever, and me, I was like the little kid sister that you didn’t really know as much about.

I wasn’t as famous, and so therefore I was able to maybe disappear into a role like A Walk to Remember a little bit more easily.

When it came to the fashion for the premiere, I remember my stylist getting this Chanel dress scent from France, and it was a big deal. It was like a full Chanel look, which I had never done before. And there were these little tiny kitten heels with pearls. The shoes, they were beautiful, and [the dress] was this sort of like peach chiffon, kind of low-waisted.

It felt like something I would have seen on Sandra Bullock or Gwyneth Paltrow, women that I had on pedestals. These are movie stars that I could only dream about calling myself an actor alongside of them.

And a very different color palette. Because we had seen you in lots of pinks and brights and purples, and this felt like a new era.

What is an outfit that you wore on repeat in 2006?

It was definitely a [Citizen’s of Humanity] jean in 2006. Some sort of maybe sheer-ish tank top that you could see the bra underneath. Multiple necklaces, maybe a skinny scarf.

But then I always had some sort of third piece, so it was usually like a lightweight-ish cardigan, maybe a jersey or something, maybe a print, maybe a color.

I feel like also I did a lot of Phillip Lim in 2005, 2006.

Denim and a button-down. I’m very much “Mom.” Easy.

I think you’re “cool Mom.” You and I share a love for Jamie Haller because it feels like this is a woman who’s a mom, who’s in our general age range, who’s making stuff for us.

[She’s] making stuff for us that makes us feel put together and cool without it feeling like trying too-hard.

Oh my! I mean, I’m wearing them right now. Literally, she is my uniform. Whatever she does and makes is my uniform.

This interview has been edited and condensed for clarity.