The first outing held in 2011, Dapper Day increased in popularity, growing to attract as many as 25,000 participants, with related events now including Walt Disney World and Disneyland Paris.
The inspiration is connected to a childhood experience Jorgensen had, in which his family travelled to Winnipeg, and encountered a store called "Dapper Dan".
After taking one of the free promotional pins from the store, Jorgensen asked his mother what the word "dapper" meant, to which she responded, "It means you’re well-dressed — smart and sharp.
In renderings by John Hench, Herbert Ryman, and other artists, the park's visitors appeared to be dressed in era-appropriate clothing for sophisticated entertainment, such as a night at the opera.
[2] Many of the attractions imagined in the original design developed into the rides and parks that stand today; Jorgensen wanted to see that full picture (guests included) come to life.
In an pushback against this relaxed park attire, Jorgensen imagined a day dedicated to "dapper" dress where people would not feel uncomfortable expressing their personal style.
Active and retired military are encouraged to wear their service uniforms or dress blues; however the organizers request that costumes or cosplay be reserved for other events.
[8] Dapper Day produces a variety of accessories including parasols, folding fans, silk scarves, pocket squares, lapel pins and brooches, with new designs each spring and fall.
Exhibitors and sponsors have included Brooks Brothers, Cirque du Soleil, Walt Disney Pictures, and Simplicity Patterns.
The hall also features a bar, swing bands providing live music, and a pomade parlor for styled hair touch-ups.
[18] The show includes pictures of park-goers dressed in 1950s and 1960s fashions, as well as attractions that have since been retired, such as The House of the Future, the Skyway, Skull Rock, Rainbow Caverns, the Flying Saucers, and Carousel of Progress.