Fashion Regrets? Chad Michael Murray Has a Few

Chad Michael Murray leans into the velvet couch we’re sitting on, locks eyes with me and switches into a conspiratorial tone. “This is something no one else knows,” he begins. I’ve just asked him if he’s ever committed a red carpet faux pas, and his eyes have lit up in a mischievous, get-a-load-of-this kind of way.

“I, um, I tried to inside-out jeans.” He pauses for effect, then explains. “I thought, ‘You know what? This is gonna catch on someday.’ So, I turned my jeans inside out, and I cut the back seam of the pocket so I could still use them. I was like, ‘Great, it looks like patchwork!” His hands gesticulate in the air. “It didn’t catch on, because it’s hard to button the pants, you know, that whole part…it was a whole thing.” (Everyone around us has burst out laughing.)

At this point, the fashion-regret floodgates are open. “I want to punch myself in the face for this one red carpet look,” he continues. “I was trying to be kitsch and cool and come up with something funky that I thought I could pull off. Boy, oh boy, was I not a fashionista. I wore this gosh-awful fedora backwards and these yellow glasses…”—he recoils at his own description—“Horrible. Awful. Bad!” All things considered, some style mishaps are inevitable when you’re the subject of affection for an entire generation.

Immortalized as the ultimate dreamboat of 2000s pop culture, Chad Michael Murray has played everything from the misunderstood football star in A Cinderella Story to the motorcycle-riding bad boy in Freaky Friday. (He recently reprised the latter for Freakier Friday. “I had to ask myself: What was Jake doing for the last 22, 23 years? Who is he?") Today, the manicured man before me is a sum of all his heartthrob parts. He’s wearing a leather jacket and a cord pendant necklace, his five-o’clock shadow is flecked with salt. His iconic blonde hair is coiffed into a perfect, unmoving flow. Despite his perceived fashion fails, he remains a world-renowned romantic interest. And that reputation is what brings us face-to-face.

We’re gathered on account of Crush, the iconic soda brand, to celebrate the launch of Orange Zero Soda—a more mature offering for those who are conscious of sugar intake. Ingeniously, the brand tapped Chad Michael Murray—now married and a dad of three—to be the face of its campaign: Your First Crush, All Grown Up. The kickoff Toronto event is a prom recreation, complete with orange-flower corsages and Murray as everyone’s dream date. Nostalgia is also a theme—something the actor knows a thing or two about.

After contemplating his past clothes, he reflects on his flaxen hair, which underwent a range of try-anything transformations throughout the six seasons of One Tree Hill. “I was uncomfortable in my skin,” he says of his younger years. “So I was like, ‘What can I do to my hair?’” When season 1 wrapped, he was told not to make drastic changes to his appearance. “I was 20-something; I was stupid. So I was like, ‘You can’t control my hair!’” He shaved his head in retaliation. “But then we got to season 2, and they turned it into a mohawk in one episode to pick on me.”

In person, he still has all the makings of a true teen idol. (Maintains unwavering eye contact; can make an entire room laugh; is somehow pulling off salmon-coloured jeans.) Yet decades later, his charm is balanced by a cocktail of self-deprecation, dad-like gushiness and folksy sing-song delivery. “I am so grateful for my life,” he says when we first sit down. “I’m not saying that as a trendy word—I’m talking genuinely understanding what that word means. I’m just grateful all the time, and I’m not sure I was when I was younger.”

His hair has similarly matured. It’s perhaps longer than ever—a result of it having taken on a “life of its own” during Covid. It frames his face with lion-esque volume and cascades behind him in a mosaic of sandy streaks. “I’m not hyper-focused on it like I was back then,” he tells me. “When you’re 20, you see everything in the mirror. But now, I’ll look at myself at the end of the day and go, ‘Dude, was that on my face this whole time?’ and it’ll be, like, yogurt from when I was feeding the baby.”

With that, the 43-year-old disappears into the mist of the crowd, twirling around tulle-wearing fans and dutifully recreating prom poses. In action, he effortlessly slips back into the role of everyone’s first crush. Except these days, he prefers to keep his pants right-side-out.