Madonna's Daughter Has Grown Up To Be Gorgeous

She's the eldest child of the Queen of Pop, but Lourdes Leon is by no means a princess. "There's no diva behavior or anything like that," a former classmate of Leon told the Daily Mail. "She's really aware how people might judge her and doesn't want a bad reputation." Leon, the daughter of Madonna and her ex-partner, actor Carlos Leon, has been wary of the pitfalls of celebrity life from a young age. Unlike her world-famous mother, Lola has done everything she can to keep a low profile, shunning sit-down interviews and refusing to make her Instagram available to the public. "I have a lot of people judging my every move," Leon told Vogue. "It's important for me to not let it rule my life."

Leon's former classmate said Lola's persona "couldn't be more different" from her mother's, but she looks more and more like Madonna every day. Madonna's daughter is in her twenties now and has grown up to be gorgeous — inside and out. Let's take a closer look at this young woman's fascinating life.

Madonna and her daughter launched a joint fashion line in 2010, when Leon was just 13 years old. Aptly named Material Girl, fellow celeb spawn Kelly Osbourne (the face of Material Girl's fall 2011 campaign), said Lola had already developed a keen eye for fashion. "I'm really enjoying being the face of Material Girl," the former Fashion Police co-host said (via E! News). "I love being part of a brand for girls and having the opportunity to work with Lola, who has an amazing fashion instinct."

One year after the Material Girl clothing line hit hangers at Macy's, Leon and her famous mom made inroads into the beauty sector, launching a collection of body care products. Speaking to Teen Vogue, a 14-year-old Leon revealed that creating the extensive range gave her a headache, and she wasn't talking about the logistics. "I had to smell hundreds and hundreds of different scents while smelling coffee beans in between," she said. "I had such massive headaches afterwards!" The brand became a headache for her mother, too — a California clothing company hit Madonna with a lawsuit, claiming it had previously trademarked the name Material Girl. Despite the legal trouble, Material Girl is still going strong to date.

Lourdes Leon and her mother became business partners when the former was just 13. Their relationship started to suffer around this time, but it had nothing to do with their burgeoning clothing brand. When Madonna sat down with Vogue in 2019, she revealed that the dynamic between her and her eldest child changed drastically when Leon became a teenager and got her first smartphone. The Queen of Pop told the fashion mag that she was opting for a different approach with her adopted son, David, who had yet to get his own phone at the time.

"I'm going to stick that one out for as long as possible, because I made a mistake when I gave my older children phones when they were 13," Madonna said. "It ended my relationship with them, really. Not completely, but it became a very, very big part of their lives. They became too inundated with imagery and started to compare themselves to other people, and that's really bad for self-growth." 

That wasn't the first time that Madge expressed regret over her decision to give Leon a smartphone. In 2013, the singer and actress revealed that her daughter had "stopped talking" to her the second she got her hands on an iPhone (via Metro).

Lourdes Leon hit the headlines for all the wrong reasons in 2012, when a picture of her puffing away on a cigarette found its way online. Madonna's daughter, only 15 years old at the time, was out and about in New York City with friends when she was snapped smoking. A pair of dark Ray-Ban sunglasses covered her eyes, but there was no denying that it was Lola in the photograph. If her Madonna-like looks didn't give her away, her nose ring (which her father had explicitly forbidden her from getting) sure did. "I don't approve of anyone smoking, most of all my daughter," Madonna told the Today show (via Metro) when the incriminating shot of Leon began circulating. "I wasn't very happy."

It didn't take long for people to start pointing out the hypocrisy in Madonna scolding her daughter. Madge has smoked in her music videos on more than one occasion, including 2012's "Girl Gone Wild," in which she seems to glamorize cigarettes. The pop star denied that she had anything to do with Leon picking up the habit. "I don't smoke," she told Today, defending the aforementioned video. "That's just an accessory ... There's a difference. [Leon] smoked that cigarette before I did that video."

Lourdes Leon started smoking at a young age, and it turns out she was an underage drinker, too. Madonna's daughter used to write a blog about her life as a student at a prestigious New York high school, and in one 2014 entry (via E! News) she said that she "may or may not have had some champagne" at her senior prom. A little champagne at prom isn't the worst crime in the world, but questions were asked the following year when an underage Leon was spotted drinking Bud Light at one of her mom's concerts.

During her 2015 appearance on The Jonathan Ross Show, Madonna admitted that she had a laid-back attitude about alcohol and drugs, despite the fact that she's never really enjoyed the latter herself. "I just ask my daughter to make wise decisions and to do things in moderation," she said. "I am not going to say, 'No, don't do it,' because that's just absurd and it's not fair. Yeah, I did it, so..." 

That attitude apparently worked wonders in this particular case because Lola apparently isn't interested in doing drugs. "Always remember to choose hugs not drugs because THAT'S always been MY motto," she wrote in her blog (via Yahoo!)

There's nothing unusual about a 16 year old getting a job for the summer, but not many teens get the chance to go on tour with a pop star. "[Leon is] definitely going on tour with me," Madonna told Larry Flick of Sirius XM (via Page Six) around the time her eldest was caught smoking, "I have to keep my eye on her." Madge was about to hit the road in support of her 12th studio album, MDNA. Leon was tasked with helping out the wardrobe team backstage, as she explained in her blog.

"I thought I would tell you all about the joys of folding underwear," Lola joked (via Yahoo!) "All of my friends were getting summer jobs and I wanted one too — mine was a little unconventional, but still a great experience and a lot of fun. Being in the wardrobe department meant me and a few other girls dressed the dancers during the show when they had quick changes. Thirty seconds to totally dress a sweaty dancer can be insane and provoke mucho anxiety." The teen described her high-pressure summer gig as "pretty cray," but she clearly had the time of her life. "I loved every minute of it," she said.

When Madonna posted a photo of the University of Michigan's merchandise store to her Instagram in 2014, she sparked speculation that her daughter had chosen to study there. The Queen of Pop attended the Ann Arbor institution herself in the '70s (she wound up leaving to pursue a career in dance, which obviously paid off big time), and she made no secret about the idea that she wanted Lourdes Leon to do the same. "I keep telling her Ann Arbor is an awesome place," the superstar said back in 2012.

Of course, being Madonna, she's used to getting what she wants, and that's exactly what happened in this instance. The Detroit Free Press confirmed that Leon had chosen to join the university's School of Music, Theatre and Dance. "She's really enjoying her time in Michigan and meeting new people," a university source told the Daily Mail at the time. "However she does get homesick so travels most weekends. She's balancing her studies pretty well for the time being but there's a worry that might not last." 

Those concerns proved unfounded. According to W magazine, Lola completed four years of study at the University of Michigan.

Reporters at the Daily Mail managed to establish contact with one of Lourdes Leon's supposed classmates at the University of Michigan. According to that source, Madonna's daughter wasn't really the outgoing type. "She's not as sociable as many people would have thought," her fellow student told the British tab, though the insider did add that Leon was "slowly coming out of her shell." 

Leon apparently felt comfortable enough to start dating, though former Michigan football player Chase Winovich had to tell a little white lie to get her to go out with him. "I emailed her and told her I was trying to join the School of Music, Theater and Dance," Winovich revealed on The Rich Eisen Show. "So one thing led to another and we went on a date." The defensive end pulled out all the stops, ordering every appetizer on the menu and finishing off the date with a magic trick. "You had to put this powder on each finger and then you snap your fingers and it makes an explosion, very impressive," he said. "Her eyes lit up. She's like, 'Woah, what was that?' I made an impression on her. And then she's like, 'Do it again!' So I was like, 'I can't! That's not how that works!'" You have to admire his commitment, but Winovich said that wasn't enough to secure him a second date with Lola.

When Lourdes Leon enrolled in the University of Michigan's School of Music, Theater and Dance, everyone assumed she was training to become the next Madonna. However, despite her apparent abilities (her mother described her as "insanely talented" and "incredible at everything she does" during an interview with Vogue), Leon doesn't seem the slightest bit interested in becoming a star. Rather, Lola is eyeing the fashion industry and has been dabbling in that scene since she was a little girl. 

At 5 years old, Leon attended the opening of the Versace retrospective at the Victoria and Albert Museum with her mother, who is a close friend of Donatella and the late Gianna Versace. In 2016, Lola sat next to Madonna and Zoë Kravitz at an Alexander Wang show and she also appeared in an ad for Stella McCartney's Pop fragrance. But it wasn't until 2019 that Leon stepped out as one of the hottest new models on the scene. "Her inclusion in Miu Miu's Spring 2019 ad campaign, alongside other young talents like Zazie Beetz and Maya Hawke, signals her arrival as a fashion It girl without question," reported W magazine. It looks like Madge's eldest clearly has a bright future on the catwalk.

For Lourdes Leon, daring to be different is in the blood. Her mother has rocked several out-there styles over the years, and Leon's clearly not afraid to embrace an outrageous look, either. In September 2016, she wore an incredibly racy outfit for a ladies night with her girls. Madonna's eldest wore a thin (think tissue-paper thin) lingerie-like top that left nothing to the imagination. She even donned matching pants, seemingly going for broke with the get-up. It takes major guts to leave the house like this, and Madge's gorgeous daughter has only grown bolder in the years since.

In 2018, Leon gave off what Hollywood Life described as "major mermaid vibes" when she appeared at New York Fashion Week wearing shredded jeans and what can only be described as a seashell bra. She accessorized her in-your-face outfit (part of designer Rio Uribe's Gypsy Sport Spring Summer 2019 collection) with a green leaf headpiece and a pair of cat-eye sunglasses.

Most eyes were fixed on Leon's seashell bra when she made her NYFW debut, but those in attendance also couldn't help but notice something else about Madonna's daughter that day. Her legs were visible through the rips in her jeans, and it was obvious that she'd chosen not to shave them. Lola is big on self-acceptance, which is what drew her to fashion in the first place. "I go through this struggle myself, [where] women's bodies have been made so public that everyone feels like they need to comment," she told Vogue after joining Stella McCartney's Pop campaign in 2016. "I love when someone doesn't pretend to be someone they are not."

Unfortunately, not everyone appreciates Leon's efforts to encourage body positivity. In 2017, a paparazzi pic of her enjoying some beach time with friends revealed her unshaven armpits. According to Teen Vogue, trolls attacked Madonna's daughter with cruel insults, calling her a "gross feminist" who wanted to "push away men" with her "disgusting" body hair. 

All that shade clearly didn't change Lola's mind on the matter — a few months later, she posed in a New Year's Eve pic with Madonna — and made no effort to hide her underarms. The bullies came after her again, but others came to this gorgeous gal's defense. "Thanks Lourdes for throwing up a middle finger to societal norms," tweeted one fan.

Lourdes Leon was into Timothée Chalamet long before 2017's Call Me By Your Name became the internet's obsession. Madonna's daughter reportedly dated the critically-acclaimed actor for a spell. They're no longer an item, but it sounds like it was fun while it lasted. 

When the Call Me By Your Name cast sat down for an interview with Andy Cohen in 2017, Chalamet reminisced about the time he got to party with the Queen of Pop. "Madonna was kinda with us dancing and my buddy Joey was there and Lola was there too and we were all dancing together," he recalled (via E! News). "I usually don't talk about this stuff, but that was a good night."

It was around the time of this interview that Leon started a new relationship with a photographer and skateboarder named Jonathan Puglia. According to her friends, things have gotten pretty serious since then — so serious that Lola may be discussing marriage. "Lola and Jonathan are very much in love," an insider told RadarOnline. "Everyone thinks they're perfect for each other, despite their very different backgrounds. Madonna approves, but the families have little in common and it's not likely they'll mix much."

You might expect Lourdes Leon to pal around Hollywood and New York City with A-lister friends, but sources say that's just not her scene. According to a Radar Online insider, Lola was "horrified" when reality TV princess and lip kit mogul Kylie Jenner invited her to a party. "[Leon] couldn't believe Kylie thought she'd be receptive to a party invite and has completely ignored her — as far as Lourdes is concerned, she's not going to lower herself to even responding." 

"Lourdes was raised to hate reality TV — it's just not her world. And she's very picky when it comes to her friends," a source told Hollywood Life. "The kids she hangs with in New York are all extremely intelligent. They're all out to make an impact on the world, so they put a very high value on knowledge and education. They're much more interested in changing the world than in taking selfies."

That said, Leon has formed a relationship with former reality star-turned entertainment correspondent Kelly Osbourne. Rumor has it that Lola "idolized" Osbourne and was excited to involve her in the Material Girl fashion line.

Madonna let everyone know just how talented Lourdes Leon is when she spoke to Vogue in 2019. "I'm green with envy," the seven-time Grammy winner said. "She's an incredible dancer, she's a great actress, she plays the piano beautifully, she's way better than me in the talent department." Mothers gushing over their kids is nothing new, but what's unusual (especially in celebrity circles) is for a parent to publicly admit that their child may not be reaching their full potential. According to Madonna, the fact that Leon grew up with a doting mother and plenty of money means she doesn't have the same drive Madge had when she was her age.

"I feel social media plagues her and makes her feel like, 'People are going to give me things because I'm her daughter,'" Madonna admitted. "I try to give her examples of other children of celebrities like Zoë Kravitz, for instance, who have to work through that 'Oh yeah, you're the daughter of...' — and then eventually you are taken seriously for what you do. You just have to keep going. But does she have the same drive that I have? No." 

Perhaps she'll share some of her talents with the world one day, but it seems that Lola is clearly in no rush to pursue recognition. We can respect that, and even though it may be a hard pill to swallow, we suspect Madonna will accept that, too.