The What, When, and How of Disney’s Dapper Days

The What, When, and How of Disney's Dapper Days meg-landrito-gUXnBDLpzOw-unsplash  Photo by <a href="">Meg Landrito</a> on <a href="">Unsplash</a>

Last weekend saw the Disneyland Hotel Exhibit Hall come to life with vintage style at the Dapper Day Expo for 2022, and boy did it look like a blast. The event is described as a “30,000 sq ft. Expo marketplace featuring everything for fun, stylish living. Browse our hand-picked selection of vintage and classic contemporary clothing and accessories vendors, including cosmetics, jewelry, eyewear, shoes, and hats. Dance to bands performing twice daily.”

Dapper Day events are a mixture of refined-style expos, shopping experiences, and dress-up day outings to museums and parks, bringing elegant, sophisticated styling from yesterday and today back into fashion. The word dapper, by definition, means: neat and trim in dress, appearance, or bearing, and that is just the beginning when it comes to the Dapper Dan outings. Nothing is out of place in this old-world style event, no matter how simple or elaborate your attire is.

Though Dapper Day events are not technically affiliated with the Walt Disney company, they have come to be lovingly embraced by fans and the parks alike. You can find more about the history of this glamorous endeavor on the Dapper Day website.

Upcoming Dapper Day Events:

If you are looking for a future event to attend, here is what is coming up on the schedule:


  • Sat+Sun, December 10 + 11 WDW FL Holiday Outings


  • Sat+Sun, April 15+16 DAPPER DAY Expo at the Disneyland Hotel
  • Sun, April 16, Spring Outing to Disneyland CA 
  • Sat+Sun, April 29+30 WDW FL Spring Outings
  • Sat, May 13, Spring Outing to Disneyland Paris

FALL 2023 

  • Sat+Sun, Nov 11+12 DAPPER DAY Expo at the Disneyland Hotel
  • Sun, November 12, Fall Outing to Disneyland CA 
The What, When, and How of Disney's Dapper Days tyler-nix-aW8mIvCnoXI-unsplash  Photo by <a href="">Tyler Nix</a> on <a href="">Unsplash</a>
Photo by Tyler Nix on Unsplash

Planning your Dapper Day Attire

Sometimes tracking down the right pieces to put your perfect Dapper Day outfit together can be challenging. Be sure to take advantage of the Dapper Day online store, where you can find everything from apparel to accessories. If you are working with a smaller budget, you might be surprised how well you can dress up an otherwise simple outfit with a few accessories, like a scarf, fan, and parasol. If you are looking for inspiration, have a look here or see some of the images from previous events below:

Have you ever been to a Dapper Day event? Let us know your experience in the comments below—bonus point for anyone who can send me photos of their outfits.

Feature Image: Photo by Meg Landrito on Unsplash

Zoë Wood is a travel writer from Sydney, Australia. Since her first visit to Disneyland at the age of 6, she has spent her years frequently visiting Disney Parks and traveling around the world.

Join Zoë as she lets you in on all the tips, tricks, anecdotes, and embarrassments that arise from her family adventures.


Our agents will assist you in booking the perfect Disney getaway, all at no extra cost to you. Get the most out of your dream vacation by letting us assist you with dining and park reservations, provide expert advice, answer any questions, and continuously search for discounts to ensure you get the best deal possible.