Dapper Day Weekend at Disney World: A Step Through Time at Disney

Take a trip through time as Disney World guests celebrate Dapper Day weekend!
Jessica Winarski
A group of guests waiting for the parade

Twice a year, the Disney resorts transform into a golden-age dream. Reminiscent of Disneyland’s opening years, guests come wearing suspenders and bowties, petticoats and pearls, and spend a weekend in a blast from the past. Dapper Day is a fan-created and fan-hosted event held at Disneyland California, Walt Disney World, and Disneyland Paris twice a year. The spring event is usually held in April or May and the fall event is in November. Although not a requirement to enjoy the weekend at the parks, participating in Dapper Day is a fun way to meet new people, try a new outfit or hairstyle, and give respect and homage to Disney’s early years.

Group of Dapper Day goers

Dapper Day

For this article, we’re going to focus specifically on Walt Disney World, although it’s fairly similar at the other two parks. Dapper Day weekend is a three-day event, kicked off by a meet-up at Disney Springs on Friday night, usually held at the Paddlefish or Boathouse restaurants. It’s a fun way to spend an evening, getting an idea of everyone’s outfits and themes and taking pictures. The rest of the weekend, Saturday and Sunday, are spent in one of the parks. In previous years, Saturday was spent at Magic Kingdom and Sunday was at Epcot. In the past couple of years, however, the parks have changed to include Animal Kingdom and Hollywood Studios (which is the perfect backdrop for an event like this!). Don’t let that discourage you though—you can bring Dapper Day to any park, and most people split their day and park hop. There really aren’t any rules or specifics to enjoying the weekend, just do what you feel! Throughout the weekend, be sure to stop by the Dapper Day Expo at the Grand Floridian, or their Disney Springs pop-up shop, to see various merchandise and Dapper Day exclusives! To get more information on this fun event, you can follow @dapperday on Instagram, or go to dapperday.com.

Two very dapper gentlemen

What To Wear

Come dressed from any decade and showoff your best bell-bottoms, flapper dress, or three-piece suit. Many participants like to theme their outfits or the whole weekend—Disney-bounding as characters from a movie, sticking to a single decade, or even theming around something park-specific (once a group dressed like the Disneyland trash cans!). If you’re not sure what Disneybounding is, it’s essentially taking a character and making a representational outfit for them. Whether that’s through basic color blocking (like green and blue or pink and purple for Cinderella’s step-sisters) or putting a modern (or vintage) twist on a character (i.e. red pants, black shirt, yellow shoes, and a Mickey hat), Disneybounding is representing characters or rides without wearing a full-on costume.

Here are a few Disneybounding ideas to get you started:

  • One of the princesses and her prince (Ariel and Eric, Tiana and Naveen, Rapunzel and Flynn, etc)
  • Iconic Mickey’s (Steamboat Willie, Sorcerer Mickey, and Classic Mickey are just a few)
  • Popular attractions (Haunted Mansion, Tower of Terror, Spaceship Earth, etc)
  • Disney-owned franchise (Star Wars, Indiana Jones, Marvel, etc)


There are tons of vintage stores online, such as Unique Vintage, Pinup Girl, Retrostage Official, and even Amazon. However, if you’d rather shop locally, we have plenty of vintage stores in Orlando as well! These are just a few of the many shops you can find around the city:

Retromended Vintage
     930 N Mills Ave, Orlando, FL 32803

Orlando Vintage
    1500 Formosa Ave, Winter Park, FL 32789

The Owl’s Attic
    3106 Corrine Dr, Orlando, FL 32803

Stop by one of these local vintage stores, or check out the nearest Goodwill and see what they have to offer. It makes for a fun day just seeing what’s available and figuring out what you can piece together from your findings. These stores also offer an amazing selection of retro and retro-esque accessories like jewelry, shoes, bags, and hats in order to complete your outfit. 

A woman poses on the Disney grass during Dapper Day

Tips and Tricks

While Dapper Day is a fun weekend for those Disney fans that want to go a little over-the-top, it can be a little confusing at first, especially if you’re newer to the Disney bubble. Keep in mind that you absolutely do not have to dress up or participate in Dapper Day weekend if it falls on your vacation. However, if you think it would be fun and something you’d like to try, then go for it! There’s no right or wrong way to do it! Here are a few more tips for you to keep in mind when deciding if you want to participate.

  • Dapper Day does NOT require additional tickets or payments, but you DO need to have a ticket to get into the park.
  • Dapper Day is not affiliated with the Disney Parks or an official Disney event—it’s fan-created and fan-run. Please keep this in mind when asking questions, making reservations, or anything else that could be impacted by this event.
  • It is popular. This means that park attendance will be higher, hotel and meal reservations could be more difficult to make, and wait times will be longer.
  • If you want to skip the Photopass lines and watermarks on your pictures, find one of the photographers scattered around the parks that are there specifically for Dapper Day. They’re free, they’ll hype you up, and you’ll get some AMAZING pictures that you’ll be free to use!
  • It’s Florida, which means that 90% of the time it’s either hot or raining (or both!). Keep the weather in mind when planning your outfits and have a backup in case it doesn’t go according to plan.
  • Everyone is there to have fun and enjoy the weekend. Try not to get overwhelmed or too caught up in anything and just enjoy it!


The major point of the weekend is having fun, engaging and interacting with other Disney fans, and stepping back in time to see the splendor of Disney when it first opened to the public. It’s also tons of fun to answer the constant question of, “Why is everyone so dressed up?” Be sure to check out the Dapper Day website or Instagram for all the latest information, dates, and inspiration.


Photo Credits
Image by Domenik Jost / Flickr