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Teddy Swims can still remember being 12 years old when he got his first pair of Timberland boots. While the outerwear brand’s Yellow Boot has continued to top style charts for fashion-forward utility wear, for the 31-year-old singer, the shoes were simply a sturdy pair of work boots that helped him score some extra cash as a kid.

“My stepdad at the time was like, ‘Well, if you’re going to get some money, I’ll give you $10 an hour, you’re going to work 10 hours every day, and then you can go spend your own money,’” Swims recalls in an interview with Billboard. “He bought me a pair of boots, and I was out there rolling sod on a football field.”

In a full-circle moment, “The Door” singer now joins Timberland’s Iconic campaign, which launched Thursday (Sept. 12) and continues celebrating the classic Yellow Boot while spotlighting a mix of original and authentic creatives, including Naomi Campbell, Slawn and Kai-Isaiah Jamal.

You can still find Swims wearing a pair of Yellow Boots, which he finds look best with a “pair of daisy dukes” (otherwise known as jean shorts).

2024 has been an ultra-successful year for the R&B singer, who scored his first No. 1 on the Billboard Hot 100 with his soulful single “Lose Control,” which has managed to remain on the chart for 56 weeks. The artist keeps winning, being labeled by Timberland as “Iconic,” which he says is “all I ever wanted to be.”

How does one know they’re an icon? Besides being the face of a major campaign, Swims believes you have to reach Halloween costume status.

“I have a dear friend of mine that I went to middle school with and he said the definition of Iconic is when somebody can dress as you for Halloween and you could be noticeable,” he says. “For my entire life then on, I was like, ‘How can I be somebody that somebody could dress as for Halloween?’ They’ll know, ‘Oh, sh–, that’s Teddy Swims!’”

And according to the artist, it finally happened to him a few years ago when his tour manager’s little cousin dressed as him for Halloween.

“I was like, ‘I’m officially an icon, I did it,’” he adds.

And if you’re wondering how you can pull off a recognizable Teddy Swims costume, he says you simply need a fake beard, fake tattoos and jokes, “Maybe tuck a pillow under your shirt, get a little gut going.”

Keep reading to shop some of our costume picks.

For more product recommendations, check out ShopBillboard‘s roundups of the best platform boots, musician cookbooks and music posters.