Bailee Madison's Most Daring Outfits Remind Us She's No Longer A Child Star

We still remember Bailee Madison as six-year-old May Belle Aarons from her acting debut in "Bridge to Terabithia," but she's come a long way since then. Not long after, 2009's "Brothers" earned her a nomination for Best Young Performer at the Critics' Choice Movie Awards. Over a decade later, she has numerous credits under her belt and has gained critical acclaim for her work as a lead on the "Pretty Little Liars" spinoff and has even ventured into the music industry, releasing her single "Kinda Fun" in 2024.

As she has progressed in her career and even ventured into different industries, Bailey Madison has undergone a completely stunning transformation. The child actor who won over the hearts of millions with her gap-toothed smile is a thing of the past, and Madison has emerged as a confident, stylish woman, rather than just a child star who grew up to be gorgeous. Further, in January 2018, she launched a clothing collection with Nowadays. "I feel like if you're a little girl and you love fashion, it starts from the moment that you're born; you start putting things together, running around in fairy outfits. That was a true dream come true," she said during an interview with Coveteur in March 2018. She closed the interview by remarking on how her fashion sense is influenced. "I'm always inspired by people's style. We live in a day and age where anything can go; it's your style now. It's what makes you feel great, and I think that's a really positive light to be [shone] on the fashion industry, too." Madison has never let negative opinions dictate her personal style, and the results are some of her most fabulous, most daring looks so far.

Ah, sexy Sandy from "Grease," the signature Halloween costume for any young woman who's ready to be viewed as an adult, rather than a kid. Bailee Madison chose the classic look for the Just Jared Halloween party in October 2018, and we were hopelessly devoted to it. The "Just Go With It" alum picked out an all-black ensemble consisting of an off-the-shoulder top tucked into some pleather pants with a chunky statement belt. Madison finished off the look by coordinating her red pumps with her lip color and wearing her balayage hair in messy curls.

In March 2024, Bailee Madison stepped onto the red carpet for a Billboard Women in Music event in a floor-length Weiræn gown that had us swooning. The garment featured silver, knitted material with chain-link embellishments. The back was entirely open, making for an interesting yet tasteful silhouette that we can't say we've seen on the red carpet too many times before. Madison finished the look with a stack of silver statement earrings and pulled her hair into a low, slick-back bun.

In December 2023, Bailee Madison posted a pic to Instagram showing just how "out of office" she was during the holidays. Posing gracefully on the back of a boat (as we all wish we were), the "Good Trouble" star opted for a white, high-waisted bikini with a subtle floral pattern and a pair of retro oval sunglasses. Madison matched the color of her bathing suit to her nail polish, making for a refined lake-day look while still showing off much more skin than a child-friendly bathing suit.

Bailee Madison attended the Los Angeles Tastemaker event for "Pretty Little Liars: Summer School" in May 2024, and the actor brought the heat. For the event, she chose a ruby-red slip dress with a thigh-high slit, lined with feathers. Madison executed the rest of the look perfectly, pairing the garment with matching open-toed pumps, a sultry red lip, and a low slick-back bun. She somehow perfectly channeled a ballroom dancer, while still coordinating with the show's colors. It was certainly a bold look for Madison, but it ultimately paid off.

A few hours after the Los Angeles Tastemaker event, Bailee Madison hit up the afterparty for "Pretty Little Liars: Summer School," and once again, left us speechless. Keeping the hair and makeup from the red carpet, Madison changed into a black bikini and slipped on a crystallized, mesh floor-length cover-up: certainly one way to turn bikini tops into different, versatile looks. She finished off the look with some strappy black platforms and accessorized minimally, but the look was already sleek and sexy enough to stand on its own.

In June 2024, Bailee Madison attended the Elle Hollywood Rising event, and she arrived looking pristine. The "Brothers" alum opted for a white satin two-piece set, including a bralette and high-waisted, ultra-wide-legged bottoms. Madison once again kept accessories minimal, completing the look with some white strappy sandals. She tied her hair into a messy ponytail and did a dewy, peachy makeup look. Could it be a sneak peek into what we can expect to see Madison in as a bride-to-be?