“I’ve always wanted an older look,” says Penn Badgley.

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Penn Badgley Reflects on His Iconic "Gossip Girl" Sideburns

If you’ve ever binged Gossip Girl, you likely remember Dan Humphrey, portrayed by the charismatic Penn Badgley. His blend of intrigue, charm, and unique style left a lasting impression on fans. But let’s be honest: what stands out even more are those infamous sideburns from the early 2000s.

The Quest for Grown-Up Vibes

Reflecting on his time as the “Lonely Boy,” Penn recently shared his sentiments about his signature look during an appearance on the Call Her Daddy podcast with Alex Cooper. "I always wanted to look older," he confessed. This quest for maturity led him to embrace a look that still sparks conversation years later.

A Rising Star

Before Gossip Girl catapulted Penn into the spotlight, he dabbled in various acting roles. However, it was his portrayal of Dan that truly made him a household name. With the series’ rich narrative woven into the fabric of New York City’s elite, Dan’s character was a refreshing contrast—smart, artistic, and continuously trying to fit into a world that felt foreign.

Those Sideburns: A Statement of Style

Let’s dive deeper into the iconic sideburns. Interestingly, Penn revealed that they weren’t a quirky character trait nor the makeup department’s doing—it was all him. "If I could have seen in real life, the side of my head, I guarantee you, I would have never," he reflected on the podcast.

Those sideburns weren’t merely a fashion choice; they were a statement, a slice of the aesthetic that dominated the early 2000s. Think bootcut jeans, low-rise waists, and an unrestrained embrace of youthful rebellion. As Penn noted, "There’s a look to a sideburn that I always wanted."

A Fashion Moment, or a Big Miss?

While many viewers have debated whether Dan’s sideburns were a delightful quirk or a fashion faux pas, one thing remains clear: they made Dan more relatable amid the glitz and glamour of the Upper East Side. Fashion enthusiasts and casual viewers alike engage in countless debates on platforms like Twitter and Reddit, illustrating just how influential Gossip Girl was, even years later.

Stylistic Choices and Relatability

In a series known for its carefully curated fashion, Dan’s seemingly unrefined grooming set him apart. It might just have been a happy accident, but it deepened the character’s authenticity as he awkwardly navigated romance and friendships.

The Love Story of Dan and Serena

Beyond the hairstyles, Gossip Girl delivered an unforgettable love saga with the relationship between Dan and Serena van der Woodsen. Their chemistry, rich narrative, and undeniable tension kept viewers glued to their screens.

Their story was filled with ups and downs: from fateful meetings at parties to heartfelt reunions that pulled at our heartstrings. By the series’ conclusion, it became clear that their bond was unbreakable, culminating in a memorable wedding. Penn and Blake Lively’s portrayal of this iconic couple left fans both exhilarated and nostalgic.

Penn Badgley: Growth and Reflection

Today, Penn Badgley appears more self-assured and reflective, taking on darker roles in hits like You. He’s not afraid to poke fun at his past, showing that growth is a part of the journey. "Sometimes, you just wish someone had tapped you on the shoulder and said, ‘Hey, maybe trim those down a little?’" he mused.

His willingness to laugh at previous hairstyles reminds us: we’ve all had those moments where we thought we looked fantastic—until we saw the photos!

Lasting Impact of Gossip Girl

Over a decade later, Gossip Girl continues to charm new audiences on streaming platforms, proving its timeless allure. Every character—Dan, Serena, Blair, and Chuck—remains etched in the annals of pop culture. Even Penn’s once-controversial sideburns are now celebrated as a quirky piece of the show’s legacy.

In conclusion, while Penn Badgley may have sought an older look during his early Gossip Girl days, he inadvertently crafted an unforgettable character that still resonates with fans. Dan Humphrey’s sideburns serve as a reminder that even our most questionable fashion choices can become iconic. As we embrace our own style journeys, let’s take a page from Penn’s book and learn to laugh at ourselves along the way.

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