Dapper Day Returns to Walt Disney World April 24-25, 2021

by Mike LaRosa
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The Dapper Dans, also known as the “Finest Foursome Around” can be found on Main Street, USA at Walt Disney World. This four-man group performs a cappella American standards that send you straight back to the good ol’ days. And, if their delightful sound doesn’t get your attention, their colorful pinstripe suits, straw hats, spats and taps certainly will. These fanciful outfits are in part what has inspired the unofficial “Dapper Day” at Walt Disney World, Disneyland, and Disneyland Paris. After being canceled in 2020 due to closure, Dapper Day returns to the Walt Disney World April 24-25, 2021!

What is Dapper Day?

First held in February 2011 at Disneyland, Dapper Day is a story straight out of modern-day social media lore. A designer named Justin Jorgensen always wished to “…dress up without everyone looking at me.” His interest in colorful and fancy clothes would draw unwanted attention almost everywhere except Disneyland. Holding back on his idea of doing a gathering at “The Happiest Place on Earth,” he finally decided to put himself out there after going to Disneyland with two of his “usually chic” friends who had donned “tourist drag” for the day.

He put out a call on social media for anyone looking to “step out in style” to join him on Sunday, February 20, 2011, and the rest is history. Around 100 people showed up, and as quickly as a viral post, people from around the world wanted more. His second event was a “Fall Outing,” which drew 450 people. Within a year, this bi-annual event had grown to over 4,500! By Spring 2013, they’d lost count at over 10,000 attendees and landing on the cover of the Los Angeles Times. The event continued to grow, eventually leading to Disneyland hitting capacity (pre-COVID). This led to Disneyland operations reaching out to Justin, informing him that there had been 30,000-35,000 participants by their count.

Dapper Day Becomes More Than Just a Day

The popularity around Dapper Day has led to additional events, including a Dapper Day Expo, held at the Disneyland Hotel Exhibit Hall. There are also Dapper Day car shows and a line of merchandise including pins, bags, clothes, and more. Not to mention non-Disney park events such as partnerships with the Los Angeles County Museum of Art. You can now find Dapper Day playlists on Spotify, specially designed Dapper Day fabrics on Spoonflower, and a curated list of Bookshop books.

Dapper Day’s 10th Anniversary & Return to Walt Disney World

The Dapper Day events return to Walt Disney World April 24-25, 2021, helping mark its 10th anniversary. The group is planning to spend Saturday at Magic Kingdom and Sunday at Epcot, but now that park hopping has returned, we’re sure you’ll see dapper-looking folks at all of WDW’s four theme parks.

Additional information is available on their site as well as this year’s prints, including a pastel Dot Candy and a bold Candy Stripe. Of course, there are masks that match, along with fans, bows, scarfs, pocket squares, and more. As with any trip to WDW, a park reservation is required. While Dapper Day is not an event that Disney Parks officially produce, the group does have a WDW Group Reservation code offering discounts on room bookings (subject to availability) at the following hotels:

  • Disney’s Grand Floridian Resort
  • Disney’s Contemporary Resort
  • Disney’s Coronado Springs Resort
  • Disney’s Caribbean Beach Resort
  • Disney’s Pop Century Resort
  • Disney’s Yacht Club Resort

Are you planning on attending? I’ll be there! I’m enjoying attending these meetups and events now that I don’t have to jump on a plane to get to WDW.

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