Brodie Butterfield, a tech worker in Australia, walked into his job one day and saw a colleague in a vintage Dale Earnhardt Sr. shirt. Earnhardt Sr., who won seven championships in the top-level NASCAR Cup Series before his fatal crash in the 2001 Daytona 500, transcended the sport in his iconic No. 3 car. Butterfield thought he’d found a fan, greeting his colleague with: “Raise hell, praise Dale!”

It didn’t land.

“He looked at me like I had two heads,” Butterfield told ESPN. “I knew he was a casual Formula One fan, so I thought maybe he’d broadened his horizons. After probing, [it] turned out he had a tenuous grasp on what NASCAR even was.”

These days, that’s normal. Old-school NASCAR merch has been en vogue for years, whether it’s authentically vintage or freshly printed for PacSun. With the modern “Y2K” revival of ’90s and 2000s fashion, it’s only getting more relevant. Normal folks are in on it, and celebrities like Kendall Jenner, Justin Bieber and Diplo are, too. Drake wore an Earnhardt Sr. jacket in March and a Mark Martin one in April.

NASCAR streetwear is in. The challenge is bringing NASCAR along with it.

“The idea that Drake even mildly knows who my dad is, is cool to me,” Dale Earnhardt Jr. told ESPN. “I got a chance to interview him at the Kentucky Derby last year, and I don’t think he knew who I was. He still might not know who I am, but he’s wearing the jacket.

“I’m certain somebody said, ‘Hey, here’s who Dale Earnhardt was.’ He might have gotten at least a two-minute refresher course on what the jacket was all about. I think if that’s all it is, that’s great. But if Drake ends up coming to a race and wanting to learn more, I think that will encourage a lot of people outside of that NASCAR bubble to come check us out.”

Earnhardt Jr. said that’s always been the challenge: making NASCAR and its personalities mainstream, like his father or Jeff Gordon. If doing that means playing into nostalgia, the Y2K renaissance is the perfect time.

“It’s funny,” Earnhardt Jr. said. “We kind of shift from decade to decade. We were obsessed with the ’80s. Before that, the ’70s. Now, everybody’s going: ‘Oh man, everything was better in the ’90s.’

“I think we should absolutely lean into the imagery and pop culture, but also what was happening in our own sport. Jeff Gordon was becoming a national — if not a global — icon, and I think we peaked around 2004. The ’90s was the buildup to that.”

Much like pop culture, modern NASCAR is trending toward the ’90s. North Wilkesboro Speedway — a beloved North Carolina track that hosted NASCAR’s top divisions from 1949 to 1996 — is back on the schedule after sitting in decay, thanks in large part to Earnhardt Jr.’s efforts to revive it. Meanwhile, the people behind some of NASCAR’s most iconic apparel are dialing back the years on their work.

Ryan Williams, a designer for Earnhardt Jr.’s JR Motorsports race team, remembers how his father wore giant NASCAR shirts and jeans when he was growing up. Back then, he hated it.

“I would be like, ‘I’m so embarrassed for him to pick me up from school or be walking around in the Home Depot with him. What is he doing?'” Williams said. “Now, it’s so fashionable to wear your dad’s clothes, and wear these big, goofy NASCAR tees. I’m so fortunate that’s a thing, because it’s my entire wardrobe.”

It also inspires Williams’ work for JR Motorsports. The team’s website is full of shirts that have throwback cues or follow a theme, like one with driver Justin Allgaier‘s car getting abducted by aliens in a cornfield. The sponsor on the shirt, Brandt, sells agricultural products.

“I’ll usually get on a kick where I’ll watch a movie or something, then in the shower later, I’ll come up with the idea of doing a shirt around it,” Williams said. “I think I watched ‘Signs,’ and then I was like: ‘Brandt. Professional agriculture. Crop circles. That sounds like a good idea.'”

Themes were common back in the day. They’re also what inspire Harris Lue and Emily Butler, who design graphics and apparel for NASCAR drivers and teams through their firm, Lue Creative.

“I think the beauty of the old merch is, there were so many people doing it,” said Lue, who wore a ’90s space-themed “Yates Rocket” NASCAR shirt while we spoke. The shirt had a starscape background, blue beams of light all over and Robert Yates Racing driver Ernie Irvan‘s No. 28 car depicted as a hovercraft in the center.

“There were so many different vendors and printers that everything was unique,” Lue continued. “[If] they were designing for Robert Yates and the 28 car, they were coming up with things just for them. Now, everything has become so streamlined that a lot of it is templated. You can buy the same Ross Chastain shirt as you can the Brad Keselowski shirt.”

“Now, they can just take a photo and plop it in,” added Butler, who sat next to Lue in her own space-themed shirt based on a ’90s Bill Elliott car. “To a lot of people, that’ll get the job done. But it’s art, and it should be art. People like when the work has been put in. There’s an effort behind it, and it’s really authentic and made special for them. I think that’s the difference between modern art and retro art.”

“In the long run,” Lue said, “if you make something cool enough, people who aren’t even into NASCAR might buy it.”

Lue and Butler saw that happen with a shirt they designed for Bubba Wallace and his sponsor, McDonald’s. The shirt showed Wallace celebrating with a fountain drink in hand, his upper body hovering over his 23XI Racing car as it spilled out from a carton of fries.

“It sold out because it was cool,” Lue said. “It was full blast, and it was fully McDonald’s.”

“We saw those everywhere,” Butler added. “[Lue] was at some random concert, and they were everywhere.”

For as often as NASCAR gets criticized for racing “rolling billboards,” Lue and Butler think for some buyers, it’s the branding that sells.

“The way that ’90s and 2000s NASCAR blended branding and racing, there’s never been anything like it that I’ve seen,” Lue said. “All the ball sports now, they’re putting logos on jerseys, but NASCAR and racing pioneered that. We found a way to sell every sellable space, and the merchandise itself — I mean, people buy M&M’s stuff and have no clue who Elliott Sadler, Ken Schrader or Ernie Irvan are. They just see M&M’s.”

That was the case for Flasch, a 25-year-old musician and content creator in Los Angeles who goes by just their first name. They started collecting throwback-style NASCAR jackets after visiting Japan and seeing them “in a bunch of stores.” When they got home, they found a brown M&M’s one for $20.

“I thought they were super cool,” Flasch told ESPN. “I got the brown one because it was my first one I saw in the USA, but I really liked the neutrality of it. I love the M&M’s branding and all the logos. To be honest, I don’t really care who the race-car driver is.”

Flasch, whose favorite jacket is a bright-blue Oreo one, almost went to a NASCAR race for their birthday last year. The plans fell through because of COVID.

“I would totally love to go to a NASCAR event in person,” they said. “I don’t really watch any sports, but I think race cars are cool even though I don’t really like driving in real life. I even have a lyric in my most recent song called ‘Popstar.’ The chorus is, ‘I wanna be a pop star, so I can drive a race car.'”

For some, vintage NASCAR is about the brands. For others, it’s about the designs. For Earnhardt Jr., it’s often about appreciating the past — the sport’s, the world’s and his own.

“We have a habit of thinking that everything in the past was better,” Earnhardt Jr. said. “We do that with music, we do that with fashion, and in NASCAR, a lot of those things remind me of my childhood. They remind me of a more innocent time, or what felt like an easier time. It was probably anything but easy.

“For me, there’s this part of the history of the sport that I never got to experience, and that was in anything from the ’70s on earlier. There’s always this pursuit of trying to get as close as you can to knowing what it would’ve been like to be there, and there’s also this never-ending quest of learning about my father — learning new stories and little anecdotes, and filling in the gaps of things about his career that I don’t know.”

Butterfield, meanwhile, keeps running into colleagues wearing vintage NASCAR merch. It remains to be seen if they’ll become fans.

“[Since the Earnhardt Sr. shirt], I’ve had two additional similar experiences with colleagues; one wearing a Kyle Petty shirt and the other wearing what I assume is a bootleg official’s jacket,” he said. “Both admitted to being fans of the ‘Cars’ film franchise, but neither followed racing of any kind.

“None of the three culprits could shed any light on why, other than: ‘It looks cool.’ I agree.”

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