As Who What Wear celebrates its monumental 20th anniversary this October, the publication is dedicating its milestone month to honoring the tastemakers, style leaders, and cultural icons who have shaped the fashion industry and pop culture landscape since the brand’s inception. For the latest installment of The Who What Wear Podcast, host Hillary Kerr sat down with multi-hyphenate star Mandy Moore to look back on a remarkable career spanning more than two decades.
From her unexpected discovery as a teenager in Florida to dropping her breakout 1999 pop hit "Candy," transitioning into critically acclaimed acting roles in A Walk to Remember and This Is Us, and her current role as a chic mother and style aficionado, Moore offered a candid and nostalgic look at her evolution in the public eye.
Reflecting on her whirlwind journey, Moore shared the unlikely story of how she broke into the music industry at just 14 years old. Growing up as a self-described dorky musical theater kid in the suburbs of Orlando, Florida, her initial aspirations were centered around Broadway. However, a pivotal moment changed the trajectory of her life when she witnessed a peer her own age singing the national anthem at an Orlando Magic basketball game.
"I was like, ‘You can do that?’ It was such a huge light-bulb moment for me," Moore recalled.
After submitting a singing tape and securing an audition, Moore quickly became the de facto national anthem singer for various sporting events throughout Orlando. That regional exposure eventually caught the attention of songwriters and producers, who helped her record demos. In a true pre-internet industry fairytale, an unfinished demo tape eventually found its way through a chain of connections—including a gentleman working for FedEx—directly to an A&R executive at Epic Records.
Before she had even turned 15, an executive flew from New York to Orlando to hear her sing. Moore completed a quasi-audition, signed a record deal in the winter of 1998, and began recording her debut album in 1999. Soon after, she found herself opening for pop powerhouses like *NSYNC and the Backstreet Boys, setting off a chain reaction that solidified her status as a late-90s pop icon.
Remarkably, Moore revealed that some of the very tracks she recorded during those initial sessions as a teenager made it onto her debut album. Looking back, she laughed at the surreal disconnect between her real-life experience and the material she was recording. At 14, she had barely experienced romance—having only kissed a boy during a game of truth or dare—yet she was tasked with recording pop songs about mature emotional experiences she had no frame of reference for.
As her music career flourished, Moore naturally gravitated toward her childhood passion for acting. Viewing any open door as an opportunity to stretch her creative limits, she began taking meetings and eventually landed an audition for Garry Marshall’s 2001 comedy The Princess Diaries. Visiting Marshall at his theater in Toluca Lake, Moore was immediately put at ease by the director’s warm, grandfatherly demeanor. Filming the movie alongside a large cast of young actors felt less like a high-pressure Hollywood job and more like attending summer camp.
The film’s premiere yielded one of Moore’s most talked-about early fashion moments: a pale, low-rise acid-washed denim suit paired with a black tank top and thick-heeled white sneaker pumps. Acknowledging the outfit as a definitive product of its era, Moore noted that while she wouldn’t choose the look today, it felt appropriate at the time. As a supporting player standing alongside leads Anne Hathaway and Julie Andrews, she viewed the casual yet distinct ensemble as a way to take herself seriously as a young artist without overshadowing the film’s stars.
The transition from a supportive ensemble player to a leading lady arrived shortly thereafter with the 2002 romantic drama A Walk to Remember. Stepping into the dramatic lead required a distinct physical transformation—most notably, dyeing her signature blonde hair dark brown. Moore humorously recalled that the press tour for the film was dominated by questions about her hair color and whether she felt she was suddenly taking herself seriously.
Unlike other pop superstars of the era like Britney Spears, Madonna, or Christina Aguilera, whose ubiquitous public personas made it difficult for audiences to separate them from their celebrity, Moore felt she occupied a different space. Because she was perceived as a lesser-known, younger-sister figure, audiences and casting directors found it easier for her to disappear completely into dramatic roles.
The premiere of A Walk to Remember also marked a significant milestone in Moore’s fashion evolution. Her stylist sourced a peach chiffon, low-waisted Chanel dress directly from France, complete with tiny kitten heels adorned with pearls. For Moore, wearing the sophisticated European design felt like a watershed moment, allowing her to channel fashion inspirations like Sandra Bullock and Gwyneth Paltrow and step firmly into the world of respected cinema.
As the decade progressed, Moore’s personal style shifted alongside her career. Looking back at her wardrobe choices from 2006, she recalled a uniform built around Citizens of Humanity jeans, sheer tank tops layered over visible bras, multiple necklaces, skinny scarves, and a lightweight layering piece like a printed jersey cardigan or a Phillip Lim design.
Today, Moore’s aesthetic has evolved into something much more practical, grounded in the realities of motherhood. Her current daily uniform relies on classic denim and a comfortable button-down shirt. She also shares a mutual admiration with host Hillary Kerr for designer Jamie Haller, whose footwear and apparel provide effortless, put-together style without sacrificing comfort. For Moore, who proudly wears Haller’s designs on a daily basis, contemporary fashion is all about feeling effortlessly cool while navigating the busy life of a working mother.