Bailee Madison's Complete Transformation Is Truly Stunning

Even though Bailee Madison is only in her 20s, the young actor has been in the industry for over a decade. Best known for projects like "Don't Be Afraid of the Dark" and "Pretty Little Liars: Original Sin," Madison has evolved and grown in the spotlight, following her dream of working in a creative field. "It's so interesting looking back because I've been fortunate to spend basically my whole childhood, tween, and teen years in this business," Madison told Rose & Ivy in 2021. "Being creative and aware of the next thing had to be instilled in me from a young age. I started realizing that I loved being creative in more than one landscape probably when I was 15 years old. ... I realized I had a lot more I wanted to say and do and sometimes you have to pave your own opportunities yourself," she added.

Today, we're focusing on the star's undeniable transformation from a childhood actor to a grown-up star while paying extra attention to all things Glam, including her fashion, beauty, and health over the years. Bailee Madison is one name we're sure to hear plenty more of in the future, but for now, let's take a trip down memory lane and revisit her journey from 2007 to now.

Bailee Madison made her acting debut in the 2007 fantasy film "Bridge to Terabithia," and with that, plenty of doors opened for the child star. "Mom always told me when I was done with [Terabithia], you have to stay humble Bailee," Madison revealed in 2010 (via Teen Vogue). "She continues to say that every day. Bailee, humble. Bailee, humble."

And while her career had evolved by 2009 thanks to projects like "Brothers" and "Phoebe in Wonderland," the star continued keeping her feet on the ground. Even though being an actor from a young age has had its effect on the star, Madison has been open about her mental health, even addressing that being a child actor often comes with its own set of issues. In 2024, Madison reflected on her childhood to Wonder Mind, saying, "I had to understand that I could acknowledge things that might have dented me a bit and understand that there's beauty within that but still allow myself to be like, 'Oh, that's something that's not healed yet. That's something that's open that I might be taking with me that might be triggered by something.'" Well said!

By the early 2010s, tween Bailee Madison had already established herself as a talented young actor as she also starred in the horror movie "Don't Be Afraid of the Dark." In 2011, she appeared in the Disney Channel hit show "Wizards of Waverly Place" alongside Selena Gomez, who's had an equally stunning transformation — and just like that, red-carpet appearances became a regular for Madison. In 2024, she admitted to Teen Vogue that being a young Hollywood star also came with plenty of stress. "Everyone was really worried because they were like, 'You're really young. People love to talk. It's hard growing up in general let alone under a microscope, and now you're adding how you personally live your life and your beliefs and what makes you you,'" the actor said.

Around the early 2010s, Madison's love for fashion also became clear, and she never missed a chance to dress up for a red carpet. Moreover, in 2011, the actor revealed to the Hollywood Mom blog that she adores vintage fashion. "I love the whole look of now like jumpers with like some cool necklaces and bracelets and a fun hat. So, I love that whole style. So anything that's vintage for me is great," she said.

The mid-2010s were important years in Bailee Madison's career. In 2013, she joined the cast of the sitcom "Trophy Wife," and in 2014, she became a recurring cast member of "The Fosters." In an interview with Your Teen in 2014, Madison explained that she was still living a normal teenage life despite working in Hollywood. "I have my best friends from my elementary school in Florida. I was very young when I started, and so it was important to my mom and my whole family to make sure my life had roots and that I was a kid and that I was grounded," she revealed. "Even when I was in Florida for a week, I would go to school, put on my uniform, pack my lunchbox. My involvement in the industry is like an after-school activity for other kids." She went on to say that her mom told her she would have to stop acting if she ever changed.

At the time, Madison's style was becoming a tad more grown up, as she was slowly growing into a young woman. Her red-carpet attire mostly consisted of classic and feminine dresses — a standout moment being the one-shoulder Walter Mendez dress that she wore to the 2014 American Music Awards.

Once Bailee Madison turned 16, her style became even more well-rounded, as the young star was now ready to explore edgier fashion. For Madison, this meant rocking more black clothes and adding textures like leather or sequins to many of her looks. The star's makeup also became bolder as she experimented with smokey eyes and darker lipsticks, allowing herself to express her style more freely.

Just like her personal style, Madison's career flourished. In 2015, she joined the cast of "Good Witch" as Grace Russell, a role she would end up playing until 2021. "I feel so fortunate to have been able to bring Grace to life for five wonderful years, and am so grateful to have been a part of the joy that filled homes," Madison shared on X, formerly known as Twitter, as a love letter to her journey over these years.

In 2016, Bailee Madison ventured into a new field as she became a producer for "Annabelle Hooper and the Ghosts of Nantucket," a project she also starred in. Even though acting remained her number one love, the star showed interest in other facets of the industry from a young age.

Madison's style was incredibly fun at the time, as the actor allowed herself to explore a variety of different looks. At the 2016 American Music Awards, the star showed up in a dazzling Amato Couture dress. The hot-pink color suited her incredibly well, and the fact that she matched her eyeshadow with it was the perfect cherry on top. In contrast, the look the star wore to that year's NYLON Young Hollywood Party was just as gorgeous but with a completely different aesthetic, as she went for a matching patchwork leather skirt and jacket set with dramatic '90s wine-red lipstick.

In 2017, Bailee Madison turned 18, and you could definitely tell that the star was becoming more and more comfortable in her skin — and her style. Madison ditched her subtle, light-brown highlights as she embraced a cooler, darker brown tone, and her clothing choices effortlessly switched between feminine, flirty, and casual with a dash of edginess. A big part of being in the industry from such an early age was also being a role model for young viewers.

However, while that might frighten many, Bailee Madison admitted to The Pop Culture Principle that she's incredibly grateful for the position she's in. "I very much embrace it and I am very grateful. I think growing up with older siblings, I understand what it's like to look up to someone and I try and emulate what my sister does and the beautiful parts of her," Madison told the outlet. The star, who has also been very active on social media throughout her career, adds that being transparent with her fans is a must. "I don't think it's so much pressure as it is just me trying to be as transparent, open, and honest as possible. I'm not one to ... say that I have it all together and that I won't make mistakes because growing up, that's impossible," she added.

Bailee Madison opened up to Schön! Magazine in 2018 about where she stands when it comes to embracing her own beauty. "I'm the first to say how much I love being makeup-free, and how it's the most confident I feel," the actor revealed. However, she added that the photoshoot for the magazine wasn't easy for her. "The creative team wanted my skin to be fresh and I was feeling very self-conscious and not photogenic at all. I left the shoot feeling insecure and feared that when people saw those pictures they would think that I wasn't pretty enough to be in a magazine spread," Madison said, adding, "I thought it was important to talk about my insecurities while shooting that spread because I think honesty is so important." We have to admit, it's not often that a star opens up about the insecurities that they have while on set — and knowing that they do encounter them certainly makes them more human. Madison's honesty helps shatter the image of the perfect and always put-together celebrity, proving that everyone has bad moments, even during a photoshoot.

While her 2018 red-carpet appearances remained impeccable from a fashion and beauty perspective (we adore the lighter face-framing pieces of her hair), it's certainly comforting to know that behind all the glitz and glamour is a person who is relatable and honest — insecurities and all. 

By the time Bailee Madison turned 20, she had already honed her sense of style, often gravitating toward a darker lip and subtle eye makeup. Her fashion choices often included statement pieces. For example, she was no stranger to combining sparkly glitter pants with an edgy black lace top — both of which are eye-catching pieces on their own.

The previous year, Madison revealed to Schön! Magazine that she's mostly inspired by the women in her life. "I'm inspired by so many incredible women, with my mother and my sister being at the top of that list," she said, adding that working with stars like Christina Hendricks and Mariska Hargitay left a big impression on her, as both of them have become inspirational women in her life. The star also stressed the importance the younger generation holds when it comes to the political landscape. "Young people need to know that their voices make change, they matter and that they are paving the way to a better future, for not just our generation but for generations to come," Madison said. "It's up to us and we can't back down. We need to continue to educate ourselves and speak up." It was clear that Madison was going to use her platform and fame to try and make a change and urging young fans to take charge of their future was only the beginning.

In 2020, the entertainment industry — just like many others across the globe — came to a standstill, and Bailee Madison's career was stuck in lockdown. But once projects could be resumed safely, the actor began shooting HBO's — now Max's — "Pretty Little Liars" spin-off. "We were in Covid times, and we weren't allowed to have any visitors, and we were filming [in] upstate [New York] and very much in the middle of nowhere," Madison explained to Wonder Mind in 2024, revealing that it was in 2020 that she began learning more about mental health. "I remember having this moment of: I'm doing a show that has always been a dream of mine, and I'm the happiest I've ever been. I'm also the lowest I've ever been," she said. "I didn't necessarily know what to do with that. I always try, I think, to find the joy and the positivity in everything, so it deeply upsets me if I feel like I'm more of a shell of a human." Being so transparent about her mental health struggles during lockdown certainly makes the star more relatable, and it helps continue a very important conversation on self-care.

During the pandemic, Madison's style became more streamlined as she mainly gravitated toward simple but still interesting clothing pieces, which she combined with subtle accessories. A great example of her style at the time was the oversized suit dress with puffy shoulders that she rocked to the 2021 National Memorial Day Concert.

In 2022, "Pretty Little Liars: Original Sin" premiered and undoubtedly changed Bailee Madison's career. The actor, who was a fan of the original Freeform series that ran from 2010 to 2017, was thrilled to be a part of the HBO show as Imogen Adams. "I think that was such a surreal experience growing up having Pretty Little Liars to turn to, so to be a part of something that is loved by myself and loved by so many, it's an honor, it's very surreal and humbling at the same time, and also really exciting because as someone who loves the original so much," Madison told Screen Rant in 2022.

As the world slowly tuned back to normalcy, we also saw plenty of Bailee Madison's fashion at industry events. With the new chapter of her life, Madison also dyed her hair lighter, exploring everything that a fun shade of cashmere brond has to offer. The star's style choices remained chic and fun as she explored what fashion works well with her new hairstyle. 

In 2023, we got to see Bailee Madison have fun with her hair, as the actor not only chopped her locks into a chic bob haircut but also went blond — and occasionally a bright pink, too. Of course, with 2023 being the year of "Barbie," we loved seeing the star jump on the Barbiecore trend. The haircut and color showed off a more carefree and fun side of the star's style, showcasing that there is no need to bind yourself to just one fashion and beauty aesthetic.

In an interview with Numéro, Madison admitted that when she doesn't work, taking care of her physical and mental health takes top priority. "I love being intentional on my off days and listening to what my soul and body need. Being with the people | love, cooking, journaling, going on long walks and being a couch potato while binge-watching TV shows I never get to watch are some of my favorite activities," she said. "However, it would be wrong to say that I can completely turn my creativity off. It runs through me whether it's an on day or an off day, so I enjoy embracing that and resetting my mind."

Now in her mid-20s, Bailee Madison is ensuring she does everything right — not only for her career but also her personal life. The star — who has been open about her mental health in recent years — continues to advocate for self-care. "I've started doing breathwork in the morning before I get out of bed, which is something I've always wanted to do but have really struggled with because I find it really hard to be still and quite simply to breathe," she told Wonder Mind in 2024, adding that her "mental health is a work in progress, as I think all of ours is. I think I'm way more intentional now with trying to recognize it and then also take care of it and give grace... It's constantly going to change, and my mind and my heart and my body are going to need new things as I continue to grow." The star's transparency about self-care remains an important part of why fans adore her so much.

While Madison is focused on living her life intentionally, we also have to applaud her recent fashion choices. The star has grown into a talented young artist — she even dabbled in music and released her debut single, "Kinda Fun," this January — who knows just how to make a statement with her clothing and makeup. And while we adore her transformation thus far, we can't wait to see what the cards have in store for this talented Hollywood star in the future.