Throw Your Hat in the Ring – Tiki Island Wear

Sometimes you don’t know you’re about to change direction until you’re already halfway there. You just know something isn’t working, and you realize that you could do it better. That’s how Dan McLoughlin ended up throwing his hat in the ring—his tiki hat, to be precise. And eventually, how his son handed one to the king of the ring himself: Hulk Hogan.

But we’re getting ahead of ourselves.

Back in 2019, Dan was helping plan the My Sandbar Summer Give-It-Back Party for Keys Life Magazine—a beloved local event that brought together the Keys community for a day of sun, music, and gratitude. As Operations Manager of the magazine, Dan wanted the perfect giveaway: custom straw hats with Keys Life Magazine branding. Something people would actually wear that represented the Keys lifestyle. 

However, what arrived was a mess. Damaged brims. Missing patches. Graphics slapped on crooked. Three different companies, three different disasters. So, they handed out koozies instead.

But Dan couldn’t let it go. He went down the rabbit hole—researching factories, testing materials, placing sample orders until it was done right. He then presented the idea to Allan Pope, owner of Keys Life Magazine, and they agreed Keys Life Magazine would be the perfect parent company to establish a local retail store.

Then the covid-19 lockdowns came. The storefront never opened, but people kept stopping Dan on the street, asking where they could get a straw hat like his. That’s when Dan and Allan pivoted. Forget retail. What if they made hats for businesses? Charter Boats. Construction Companies. Beach shops. People who wanted branded wear with island style. 

The wholesale model took off—first locally, then in other beach towns, then anywhere someone Googled “custom straw hats” and found Tiki Island Wear sitting at the top of the page. No ads. No marketing budget. Just a quality product, and a gap in the market nobody else had filled.

But now back to Hulk Hogan.

Dan’s stepson, Trystan, is a huge wrestling fan, especially the old-school legends. Dan heard about a meet-and-greet opportunity with Hulk Hogan, but Trystan has autoimmune issues and couldn’t handle the crowds of the public event. So, Dan’s wife Erika reached out to the general manager, and Hulk graciously offered to meet Trystan before the event. Trystan wanted to bring Hulk a personal and thoughtful gift. So, they made the Hulkster a custom straw hat.

Before the crowds arrived, Trystan walked around wide-eyed, meeting other famous wrestlers and commentators he’d only seen on TV. When he gave Hulk the hat, Hulkster immediately showed it off to his business partner, Ron Howard, and they wanted to collaborate with Dan on future projects. But even that resulting collaboration couldn’t overshadow Trystan’s joy that morning.

Since then, orders have come in from around the world and the collaborations have only continued to grow. Tiki Island Wear now produces custom headwear for Allied NASCAR Race Teams, Delta Air Lines, the U.S. Air Force, Capital One Orange Bowl, Jeep Beach, a major cruise line, and more.

Tiki Island Wear has expanded beyond straw hats, too—adding baseball caps, synthetic straw hats, and bucket hats. Every piece can feature a fully customized underbrim design, whether designed by the client or in-house.

The minimums are very reasonable: wholesale orders start as low as 25 pieces for straw hats, with other styles available in minimum quantities of 50 to 100. Whether it’s for a family event, a small business, or a nationwide campaign, Tiki Island Wear meets clients where they are.

Despite the growing business and his continued role at Keys Life Magazine, Dan always finds time for his family, which is a must when you have six kids. Every chance they get, Dan and his wife Erika load up Reese, Declan, Riley, Trystan, Ronin, and Nevaeh for a trip up to Hogan’s Hangout, Disney World, or other touristy adventures.

At the end of the day, it’s still about showing up for people—whether it’s for his family, a local business in the Keys, or a national brand looking for something no one else can deliver. If you’ve been thinking about throwing your hat in the ring—literally—Tiki Island Wear makes it easy. Learn more at TikiIslandWear.com.