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If you happen to be in Walt Disney World over the weekend of April 27-29, don’t be surprised or feel underdressed if you see crowds of folks dressed up in stylish clothing swarming the streets of the Magic Kingdom on Saturday and Epcot on Sunday. That’s because the Spring Dapper Day event is being held that weekend, and thousands of guests will participate. We first attended a Dapper Day event last November and got hooked. Here’s what you need to know about Dapper Day, and why you might want to plan your next visit to a Disney park to coincide with it.Dapper Day at Walt Disney World, DisneyBound, cosplay

What is Dapper Day?

Dapper Day is a non-Disney organization that was started in California in the spring of 2011 by Los Angeles Designer Justin Jorgensen. Essentially, it is a gathering of people dressed in vintage clothing that harkens back to the era fifty or more years ago when folks used to don their Sunday best to visit Disneyland and other attractions. That first event only had a few hundred people attend; now, while I have seen no official numbers, it’s estimated that 20,000-30,000 guests participate.

Tip: Sign up for the Dapper Day newsletter. The organization sends out all kinds of updates and gives you notice of exclusive merchandise, signings, and meet and greets.

There are events in Disneyland, Walt Disney World, and, more recently, Disneyland Paris. The organization also takes outings to various places in the Los Angeles area.

How do I participate in Dapper Day?

I had read about Dapper Day years ago, and was interested in going, but it wasn’t until last November that the stars aligned for us to attend the fall event in the Magic Kingdom. Dates are released quite a few months in advance, allowing you to get hotel reservations, airline tickets, and FastPasses in good time.

There is no cost to participate in Dapper Day because it is not an official Disney event. Your r

Regular park admission ticket will give you the opportunity to attend. There are a few ticketed expos and restaurant meetups that will occur, but there is no expectation that you *must* attend these.

Really, in order to participate, you just show up dressed in your Dapper best!

Dapper Day at Disney World, DisneyBound, cosplay

A Dapper guest poses at Disney Springs in her vintage finery

Tip: If you keep up with Dapper Day news (see tip above!), you can often snag a convention rate room at one of the Disney hotels. These rates are great, they even beat the military discount that Disney offers. But please, if you are going to use the rate, do try and participate in the event, too.

What do people wear on Dapper Day?

You will see all kinds of outfits. Some people are simply attired in dressy contemporary outfits. But many guests will be wearing vintage or vintage-inspired clothing. While there is no one single time period that Dapper Day embraces, most people are inspired by the fashions of the forties through the sixties. The important thing to know is that people do *not* wear costumes like they do for Mickey’s Not So Scary Halloween Party.

For our first foray into the Dapper world, I had in my mind a vision of what I wanted to wear, but I’m not the best seamstress, so my mom had to help me sew outfits for my daughters and myself. With some help from my mom, Amazon, and some vintage clothing shops, I was able to assemble outfits for our family.

Magic Kingdom, Main Street Emporium, Dapper Day merchandise

Special merchandise was available for purchase on Dapper Day.

Getting on the bus at Pop Century that first day was a bit nerve-wracking. There we were, dressed in our Dapper outfits and we didn’t see anyone else dressed up! Did we get the date wrong? Were we the only ones participating? But we need not have worried, as the day progressed we saw hundreds and hundreds of others dressed in their vintage finery. A purely unscientific study by my husband and myself led us to conclude that about one quarter of the people in the Magic Kingdom that day were trying their best to be Dapper.

Tip: Bring a change of clothing and store it in a locker in case you get uncomfortable in your Dapper attire (or if you want to ride Splash Mountain!). The lockers on Main Street can be opened and relocked throughout the day, allowing different members of your party to change/store clothing items as the day (and the heat!) progresses.

Some people are not only Dapper, they are DisneyBound. I have actually heard the term “DapperBound” used to describe this look.

One thing I learned that November day was that it’s hard to strike a balance between comfort and style. Luckily, my footwear was pretty comfortable, but the wig I had ordered from Amazon was not and kept slipping back off my head. I won’t be wearing a wig next time!

What do people do on Dapper Day?

Mostly, you peopDapper Day Magic Kingdom Main Street Emporium, DisneyBound, cosplayle watch as you go about your normal theme park activities. This can be *very* entertaining, as you would not believe the lengths that some people go to in creating their looks.

There are often expos (sometimes free, sometimes ticketed) held at one of the resorts showcasing Dapper merchandise and memorabilia. The Expo in Disneyland includes bands and dancing. Sometimes Disney itself gets in on the act – when we were at the fall Dapper Day event last year, there was a bunch of the retro merchandise usually sold at the Dress Shop at Cherry Tree Lane in the Emporium on Main Street, and Ashley Eckstein, the creator of Her Universe, was there for a signing.

With the opening of the always dapper Edison in Disney Springs, there is now an appropriate venue for a meet up, and there will be one happening on Friday the 27th of April.

Dapper Day is a fun event to attend, and even more fun when you participate. It’s very light-hearted and nostalgic. We’ll be attending both the Spring and Fall events this year, and I hope to attend next year as well.  Have you ever participated in a Dapper Day event?

If you want to attend one of these events at Walt Disney World, why not contact Patricia Payne and use the FREE services of All for Dreams Travel?