Justin Jorgensen, the founder of Dapper Day at Disneyland, grew up in Fargo, North Dakota. On a regular basis, his father would take the family up to Winnipeg, one of the biggest cities in the area, a few hours north.

“I remember being 8 or 9 years old,” Jorgensen says. “We were at a mall in Winnipeg, and there was this store called Dapper Dan. I took one of the free promotion pins from the store, and later asked my mother what the word ‘dapper’ meant. She said, ‘It means you’re well-dressed — smart and sharp.’”

The concept stuck.

“Since I’ve been a kid, I’ve always been an eccentric dresser,” Jorgensen says. “Eventually, the idea of dressing up at Disneyland had to be called Dapper Day.”

Jorgensen, a creative consultant, organized the first Dapper Day on the fly, in February 2011, and about 100 well-dressed guests showed up. “It was more of a park gathering,” he says. “It was not intended to be a period event — it’s more a matter of celebrating the idea of dressing up, in any manner or style.”

Jorgensen says that in some ways, Dapper Day is a rebuttal to “the idea of dressing in casual, tourist drag.” It’s also about providing a magical backdrop for people who like to get dolled up.

Credit: Brian Feinzimer

Credit: Brian Feinzimer

The first folks who caught my eye when I walked into the convention center at the Disneyland Hotel were four young women dressed as 1960s flight attendants. “Dressing up allows you to act out a certain part of your personality that you wouldn’t normally flex,” said one of the women, Caitlin (she wouldn't give her last name). “And then to combine that with tens of thousands of other people who also dress up at Disneyland — it's easy to see why we keep coming back every year.”

Kevin Mills, who's in his early 30s, works in sales and was dressed more like Jay Gatsby than Don Draper. He says Dapper Day offers an opportunity to step into a different persona. “There is an element of role-playing that is on full display when everyone is brought together in public in such an iconic space,” he says. “There’s an appreciation you see in other people’s faces when they walk by and acknowledge the care you put into your outfit, and vice versa.”

After the first two years, Jorgensen began running the biannual Dapper Day full-time. The event has grown to 20,000 attendees and now includes an expo — a niche trade show for new and vintage clothing and beauty products. There are now Dapper Days at the Disney-owned parks in Florida and Paris, and Jorgensen's long-term plans include further expanding the expo of boutiques and like-minded vendors.

But even as it continues to grow, there's an intimacy at the heart of the event.

“There’s a connection that Dapper Day creates,” Jorgensen says. “When you’re dressed up, you’re more likely to talk to someone who is also dressed up. Friendships form in line for rides. Normally, you wouldn’t want to talk to anyone in line at a theme park; you’d keep to yourself. There is a psychology about it. It becomes a big cocktail party without the cocktails.” 

Correction: This post has been updated to reflect that Dapper Days in Florida and Paris already have launched.

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