UPDATED November 10, 2025

It’s time to visit the Disney Parks IN STYLE… we’re talking about Dapper Days, my friends!

Whether you’re sporting a t-shirt repping your favorite Disney characters, rides, or foods or whether you’re wearing a full Disneybounding outfit in the parks, dressing up for the Disney Parks is a great way to add a little something extra to your Disney trips. If you REALLY love to dress up, though, you really need to know about Dapper Day, when guests in Disney World and Disneyland dress to impress!

So put on your best dress or sharpest vest and place that cute hat on your head just so as we dive into all the Dapper Day details!

What is Dapper Day?

Not familiar with Dapper Day? (Actually, make that Dapper Days because this event takes place a couple of times a year on BOTH coasts), the basic idea is to dress up in vintage outfits, just like what you might have seen when Disneyland first opened.

That said, you may also see ‘fit twists on modern day Disney themes, too!

Dapper Day is an unofficial event organized by a third party organization — which is to say, it’s not a Disney-sponsored or managed event, so you won’t find information for it on the Disney World or Disneyland websites (though, as you’ll soon learn, the Parks are welcoming to the event!). It’s brought to us by the well-dressed folks at dapperday.com. And it always delivers an especially fun time in the parks, for those who participate in full garb and for those who simply get to see all the gorgeous outfits!

Dapper Day Events

Dapper Day is a twice-a-year event that happens at both Disney World and Disneyland! 

DISNEYLAND HOLIDAY EVENT 2025

• November 15th & 16th: Pop-Up Boutique at Disneyland Resort’s Grand Californian Hotel
• November 15th: Dapper Day Eve in Downtown Disney
• November 16th: Holiday Outing at Disneyland

P.S. If you are headed to the Disneyland Holiday 2025 event, don’t miss out on exclusive savings for your hotel stay. You can save up to 36% at select Disneyland Resort Hotels. Special savings are available at Disney’s Grand Californian Hotel & Spa, Disneyland Hotel, and Pixar Place Hotel. You can book online through the Dapper Day website or call Disney Group Reservations at (714) 520-5005 from Monday through Friday, 8 AM to 5 PM. If you call, you will need to request the “Dapper Day Group Rate,” or you can also email [email protected] to book. 

You’ll notice two kinds of events are listed for each season. Dapper Day Outings are primarily what you see pictured on this page: these are the dates when park guests dress to impress for their day in the parks!

DISNEYLAND SPRING 2026 

• Sunday, April 19th:  Spring Outing to Disneyland Park

The Dapper Day Expo, which returned in Spring 2025, is an event that takes place outside of the park in Disneyland. The Dapper Day website shares: “A companion to our DAPPER DAY outings to Disneyland, shop our nearly 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, hats, and more. Plus new DAPPER DAY merchandise will be available exclusively at the Expo.” It’s “the biggest style celebration in California!”

DISNEY WORLD HOLIDAY OUTING 2025

• December 6th and 7th: Holiday Outing to Walt Disney World 
  • Saturday, December 6th: EPCOT
  • Sunday, December 7th: Disney’s Hollywood Studios

DISNEY WORLD SPRING 2026

• Saturday & Sunday, May 2nd & 3rd: Spring Outing to Walt Disney World 
  • May 2nd: EPCOT
  • May 3rd: Animal Kingdom

Dapper Day Pop-Up Shops

We’ve already discussed the Dapper Day Expo in Disneyland. While there is not a Dapper Day Expo in Disney World, you may spot a Dapper Day Pop-Up Shop around the Resort for all you dapper needs!

In previous years, we have seen we have seen pop-up shops in EPCOT and Disney Springs.

Dapper Day INSPO!

We are so thankful that so many of the Disney Parks Best Dressed Guests have allowed us to take their pictures to share here on the DFB!

We thought we’d share a few here in case you would like to participate in Dapper Day, but still need some style inspiration.

Having two seasonal events really allows for variation. While you see a lovely Spring look above (which is also perfect for the warmer temperatures), you may also opt to add a lil’ (or a LOT!) of holiday flair to your outfit for a December Outing.

If you would love some more ideas, you can check out a few of our complete photo posts from previous Dapper Day events:

• Dapper Day — Spring 2025 (When Dapper Guests at Disney World Said Farewell to the Liberty Belle in style)
• Dapper Day — December 2024 (The Disney Adults Met Gala!)
• Dapper Day — December 2023 (When the Guests at Disney World TOTALLY Understood the Assignment)
• Dapper Day — Spring 2024 (Who Wouldn’t Want to Be a Part of This STUNNING Club?)
• Dapper Day — December 2022 (When the Fans Went ALL OUT!)

How to Participate in a Dapper Day Outing

1. Mark your calendar with the dates above.
2. Plan your outfit!
3. Purchase a valid park ticket to attend the in-park Dapper Day events. In Disneyland, you’ll need a park ticket plus a Park Pass reservation for that date. In Disney World, select guests may require a Park Pass reservation for that day.
4. It’s the BIG DAY! Get dressed up and DAPPER!
5. SAY CHEESE! (Because you may discover that perfect strangers want to take your picture, you well-dressed style icon, you!)

We love to see it… Don’t you 🙂 ? ENJOY all the Dapper Day FUN!