The Lavish Life Of Bailee Madison

Bailee Madison has been on our screens since the mid-noughties, bursting her way onto the acting scene when she was just 5 years old. Of course, fans these days will likely know her best as Imogen Adams in the "Pretty Little Liars" spinoff shows "Pretty Little Liars: Original Sin" and "Pretty Little Liars: Summer School." Lovers of the franchise know that being a main player can do wonders for a young star's visibility, and Madison is no different. This born entertainer is living her best life while pushing her career forward. 

Not only are the partnerships and brand deals knocking down her door, but Madison enjoys vacations at some of the swishest spots in the United States and beyond, has a gorgeous wardrobe, rubs shoulders with high-flying stars, and kicks up her feet in a beyond beautiful home. When it comes to being young and loved in Hollywood, Madison knows how to do it right. Let's take a look at just how fabulous her life really is.

For most of us, going on a girls trip might mean throwing an overnight bag together and having a casual sleepover, or heading out to the bar for a few drinks. When you're rich and famous with a huge social media following, brands often trip over themselves to offer free stays, in exchange for a social media post saying how great the experience was. Bailee Madison got that very treatment when she and her girlfriends attended NASCAR race at Sonoma Raceway in June 2024. Taking to Instagram, Madison shared photographs of herself looking sleek and stylish with her friends.  

Not only were her outfits on point with a semi-casual twist, but Madison got access to the cars and was even able to take photos right in front of them, something not everyone is allowed to do. Some of the photos also show Madison wearing a Cakebread Cellars baseball cap and holding a glass of wine. The stunning location is a winery situated in Napa Valley, offering some top-tier wines from the region. The real question is, how do we get added to this girls trip invite list? 

The stunning transformation of Bailee Madison began when she was an adorable child actor, and now she is a fully-fledged star who is racking up the paid partnerships. A quick look at Madison's Instagram shows you that she's busy keeping up with sponsored posts. One of her partnerships is pretty impressive, as it involves the luxury car brand Cadillac. In a post celebrating the brand's new Optiq range in June 2024, the actor posed with a deep red version of the car. She wore sheer black tights with a cute black coat dress with a wide white collar. 

This wasn't just a case of popping down to her local garage in Hollywood, either. Madison got to go and enjoy the events in Paris. In other snaps from the trip away, the brunette posed in front of classic French landmarks including the Eiffel Tower. The star also managed to squeeze in some time to see tennis pro Roland Garros play a match, which she enjoyed alongside her longtime love, Blake Richardson.

Actors often find themselves having to stay away from home for long stretches of time, which can be arduous. In some scenarios, stars may be so busy that they only see the inside of a hotel room on their days off. In Bailee Madison's case, she decided to turn one of her work trips into a swanky staycation. In May 2024, the star posted a series of photographs to Instagram taken on one of Montauk's beautiful beaches. Madison looked happier than ever in the snaps, wearing a simple black dress with her hair pulled back as she walked on the sand. 

She explained to her followers that she had a photoshoot in the area and decided to take her downtime at a local resort, Marram Montauk, a place she had been to visit. "Thank you for the most tranquil, peaceful place," she gushed in the caption. "Me and my journal will see you again soon!" Though it offers a slice of luxury away from the stressors of nearby New York, this boutique residence is bigger than it may seem at first glance, boasting an impressive 96 rooms, and plenty of beachfront beauty. At the time of writing in November 2024, a night in peak season could cost you upward of $900. This tells us that Madison appreciates the finer things in life. 

Longtime fans might remember Bailee Madison from Hallmark's "Good Witch" or even from the 2007 movie "Bridge to Terabithia." Madison's numerous projects over the years mean that she's managed to establish friendships with some of her more established co-stars, such as "Mad Men" alum Christina Hendricks. The pair starred together in the 2018 movie "The Strangers: Prey at Night" alongside Martin Henderson. The horror caper was a continuation of the original 2008 movie, "The Strangers," and while it didn't exactly become a worldwide smash, it did bring Madison and Hendricks together. 

Despite their age gap, Hendricks and Madison have maintained a friendship. In April 2024, the stars reunited for a glitzy fashion event for the brand Partlow. Madison posted photographs of herself beside the redheaded "Good Girls" actor, smiling from ear to ear on Instagram. "A night celebrating @partlowofficial in their boots that are made for walking, laughing, and major girl chats with one of my favorite humans @actuallychristinahendricks," she wrote in the caption. Oh, to be a fly on the wall of those major girl chats.

Many "Pretty Little Liars" stars have branched out into different creative avenues, so it's not surprising that Bailee Madison has interests outside of acting. Not only is she able to perform in front of the camera, but Madison also loves to make music. In May 2024, she told Teen Vogue that moving in with her boyfriend, British rocker Blake Richardson, helped her push her music aspirations forward. The couple wrote her first single, "Kinda Fun," together in 2024. "It's so fun because we're writing together. We get to just wake up and have coffee and sit outside and then go into the studio and write songs, and it's really special ... a bonding experience."

Despite telling the publication that she wasn't in any rush to release more music, Madison unleashed the summer anthem "Chiller" in July of the same year. In a promotional Instagram post of herself in a bikini laughing, Madison wrote, "#CHILLER is out now! Let me know what you guys think of it! I really hope you'll dance around & feel the MOST confident." 

Madison told Us Weekly that Richardson helped her create this song, too. "We were chatting about some weird situations that I have been in lately that left an un-chill taste in my mouth.," she recalled. "From random guys whistling to me and my girlfriends, to hands just a little too low during pictures with strangers." The aim was to have fun and hopefully encourage listeners to love themselves. 

If there's one thing a young actor in Hollywood knows, it's that looking good and having your makeup on point is crucial. When you're as famous and sought after as Bailee Madison, you have your pick of cosmetic brands who want you to wear their products. Madison decided to partner with one of the biggest brands on the planet, L'Oreal Paris. The mega-corporation is a popular household name, and what's more, usually pretty affordable when compared to high-end designers. In an Instagram video in July 2024, Madison leveraged her "Pretty Little Liars" stardom to do a joint video with the original show's star, Ashley Benson. "I can always spot a pretty little lie," she wrote in the caption. "And the truth is, @ashleybenson and I both love @lorealparisusa." 

In the snippet, Madison shows followers what her lashes look like with and without the brand's Telescopic mascara. The results were impressive, but there's something that tells us Madison's fresh-faced aesthetic and sweet nature make her a great salesperson, no matter the product. Either way, this partnership is a match made in heaven and likely comes with a lot of perks for Madison, such as attending the brand's glam events, as pictured above. 

While some celebrity homes are surprisingly normal, others would make even Robin Leach's jaw drop. Madison Bailee's home isn't over the top and extra glamorous, but it's certainly chic, classy, and downright beautiful. In July 2024, Madison posted a snippet of her living room that she shares with her partner, Blake Richardson, to Instagram. The sweet photo showed the actress snuggling with her dog on a giant off-white sofa. Madison marked the post as a partnership, tagging furniture company Lovesac which is well-known for their giant, comfortable sofas. 

The series of photographs also gave fans a glimpse at what Madison's house is really like. Along with the giant couch, Madison's home features an open-plan living/kitchen space with built-in shelves, which Madison uses as a bar area. The neutral color scheme is very fashionable, as is the gold circular glass-top table and vases of fresh flowers. Even though the home looks gorgeous, it's clear that it's lived in and well-loved, unlike some other celebrity showhomes where not a thing is out of place.

To the casual observer, it may look like young stars have it all. They can usually command impressive paychecks, and get to do things that members of the public could only dream of. While that's definitely an element of it, a lot of hard work goes into attending big television or corporate events. For Bailee Madison, her calendar is stacked full of awards shows, Netflix events, fashion shows, and much more. Some of these engagements will be things she's chosen to attend, while some of them may be part of her contract when it comes to promoting her on-screen projects. Either way, Madison always turns up with a big smile wearing some impossibly stylish outfits. 

In 2024 alone, Madison attended Polo Ralph Lauren's Elle Hollywood Rising event in Beverly Hills, the NASCAR Cup, several swanky "Pretty Little Liars" events, and a screening of "Turtles All the Way Down." Of course, each of these exclusive, invite-only soirees required a carefully picked outfit. Madison's looks served gorgeous every single time, from a diamante-studded sheer black dress to a stunning red gown with feather detailing. Is there anything that this fashionista can't pull off? 

Drew Barrymore's talk show has been a hot topic since it landed in 2020. Barrymore has managed to get a host of big names into the hot seat, such as Martha Stewart, Mille Bobbie Brown, and of course, Bailee Madison. Madison appeared on the show in 2024 to discuss her personal life as well as her upcoming projects with the "Never Been Kissed" star. When it comes to appearing on talk shows, Madison is fast becoming a pro. After all, the kind of publicity this sort of appearance can generate is invaluable for a young star looking to make their mark on Hollywood. 

In May 2024, Madison also made her way to "The Kelly Clarkson Show," another of America's most popular daytime talk shows, where she was interviewed by the pop star. Also appearing that day was "Grey's Anatomy" and "Killing Eve" actor Sandra Oh. To say that Madison is rubbing shoulders with the best would be an understatement. Around the same time, Madison also appeared on "Today with Hoda & Jenna."Needless to say, she's a chat show pro. 

Can you imagine what it must be like to go to Universal Studios as part of a partnership? The theme park is the go-to destination for film lovers looking to have a fun day out, but tickets can be pricey. Luckily for Bailee Madison, she doesn't have to worry about that. In April 2024, Madison hopped onto Instagram to share a carousel of photos of herself enjoying the park, dressed in low-key casual wear and an incognito baseball cap. In one snap, she held up a cup of butterbeer — Harry Potter's drink of choice, of course — and in another, she posed alongside friends and family, all with beaming smiles. 

Like many actors who have been in the business for a while, Madison has a long-standing relationship with the entertainment company. In 2011, she attended the Los Angeles premiere of the James Marsden movie "Hop" at Universal Studios in Hollywood. She's a regular on the lot there, also appearing in 2018 to pay a visit to Hallmark's "Home & Family." Madison works hard, but she can play hard, too. Even better when you're able to turn it into a paid advertisement for a place or company that you already love.

You don't have to be an agent to the stars to know that entertainers need breaks every now and then to stop them from buckling under the pressure. Some child stars haven't coped very well in adulthood because of the responsibilities bestowed upon them at such a young age, but thankfully, Bailee Madison is flourishing. If her social media is anything to go by, Madison makes sure that she takes downtime when she needs it, often going to her favorite haunt: the beach. As well as paying visits to Montauk, Madison also enjoyed a seaside break over Christmas in 2023. She posted a series of photographs to her Instagram of beautiful sunsets and blue skies, as well as a short video of herself dancing sweetly with her longtime love, Blake Richardson. 

Madison also took to the sand to take some promotional photographs for her summer single "Chiller", and spent some time taking in the waves on a different trip in April 2024. Is Madison's penchant for fresh air, salt water, sea, and sand the reason why her skin is always glowing? Maybe we should all take a leaf out of the actor's self-care book. 

We aren't the only ones swooning over every outfit from Taylor Swift's Eras Tour. Celebrities fell over themselves to get tickets for Swift's extensive run of shows across the world. Even Prince William took his two eldest children, Prince George and Princess Charlotte, to see the pop star in action at one of her London shows. As you might have guessed, Bailee Madison got her very own chance to see the "Shake It Off" hitmaker in action when she went to one of the 2023 shows. Madison wasn't just in the regular seats with the rest of the Swifties, though. She got VIP treatment, watching the show from Taylor's Lounge which is reversed for special guests. 

Madison and Swift have crossed paths before, having been photographed together at the 2014 American Music Awards (pictured above). There's no denying that the actor is a diehard fan of the singer, as she took to Instagram to post photos from the concert, even thanking Swift's publicist, Tree Paine. "Thank you Tree and team for making the night so special and for letting me grow up at these concerts with you all," Madison gushed in the caption. "I had the time of my life."