"I always wanted to look older," says Penn Badgley Gossip Girl hairstyle choice

If you've ever watched Gossip Girl, chances are Dan Humphrey, played by the charming Penn Badgley, left quite the impression. Maybe it was his deep musings, maybe his whirlwind romance with Serena van der Woodsen... or maybe, just maybe, it was those sideburns.

Yup, those unforgettable, odd, early-2000s facial hair choices are still a talking point, even years after the show ended. And recently, Penn himself finally spoke about them.

Penn Badgley isn't just “Lonely Boy” anymore. Before he became a household name on Gossip Girl, he had a few roles here and there, but nothing as big. That show put him on the map. Since then, he's taken on darker roles (like Joe in You), hosted podcasts, and shared more of his personal growth. But back in the day? He just wanted to look grown-up.

"I always wanted to look older."

Dan Humphrey was never meant to fit in. He was the Brooklyn kid among Upper East Side royalty. That was the charm. Smart, poetic, and a little too real for the privileged world of Blair and Chuck, Dan quickly became a fan favorite. But his journey from outsider to ultimate secret-keeper was nothing short of iconic.

Let’s talk about those sideburns. They weren't makeup department magic or a character quirk written into the script. They were all Penn. He recently admitted on the Call Her Daddy podcast with Alex Cooper:

“If I could have seen in real life, the side of my head, I guarantee you, I would have never, never.”

That look? All him. He was chasing a vibe, an aesthetic that screamed, "I’m older, I’m edgy, I’m artsy." Sound familiar? It was the very early 2000s for him.

It was the era of bootcut jeans, tiny handbags, flip phones, and thick sideburns. Fashion was a little wild back then. If you grew up in that era, you probably tried something that you regret now (but maybe still secretly love?). Penn was no different:

"You know, in the early 2000s, it was like, bootcut jeans with the low-rise waist. There's a look to a sideburn that I always wanted."

We get it, Penn. We really do.

During the podcast, he seemed genuinely puzzled about why no one stepped in to help him:

"I mean, who allowed that? So many people allowed that."

We feel your pain, buddy. Sometimes, you just wish someone had tapped you on the shoulder and said, "Hey, maybe trim those down a little?"

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Gossip Girl’s styling choices

Years later, fans still talk about them. Twitter threads roast them, Reddit has full discussions, and memes are everywhere. Some fans thought it was a makeup mishap. Others were sure it was part of the character's awkward charm. Turns out, it was just Penn doing his thing.

Gossip Girl was the fashion show of its time. Every outfit, every headband, every hair flip was deliberate… except maybe Dan’s sideburns? No stylist interference, no notes. It's kind of wild when you think about it. But maybe it made Dan more relatable, a little less polished than the rest.

Okay, enough about hair. Let’s talk about Dan and Serena. Derena was the heart of the show. They had chemistry, tension, and every teen drama trope rolled into one love story. They first met at a party Dan wasn’t even supposed to attend, and from there, it was fate.

They were together, then apart, then back together… again and again. From the Pilot to the final episode, Derena fans rode an emotional roller coaster. Even when they weren’t officially dating, the longing looks and accidental kisses kept us all hooked.

By season six, it was clear: they were meant for each other. No more games. No more misunderstandings. Just love. In the final episode, New York, I Love You XOXO, Dan and Serena tie the knot. Cue the tears. And of course, we got one last “XOXO.”

Penn’s all grown up now. He’s taken on darker, more complex roles (looking at you, You), and he's shared his journey of self-reflection and maturity. From confused young actor to introspective adult, he's not afraid to poke fun at himself now.

Honestly? We’ve all been there. That outfit, that hairstyle, that one decision that we thought looked amazing until we saw photos later. But it’s all part of growing up. And if Penn can laugh about his past choices, maybe we can, too.

More than a decade later, Gossip Girl still lives on. New generations binge-watch it on streaming, and characters like Dan, Serena, Blair, and Chuck remain pop culture royalty. Even the sideburns? Yup, they’re part of the legacy now.

Penn Badgley might have wanted to look older back then, but what he gave us was a character we’ll never forget, flawed, relatable, and weirdly stylish (or not?). And while Dan’s sideburns might've been a questionable style choice, they’ve become a legendary part of Gossip Girl history. Sometimes, your mistakes become your most iconic moments.

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