Dapper Day 2023: The Ridiculously Easy Beginners Guide to this Disney Celebration

On the bright Sunday morning of July 17th, 1955, Disneyland opened its gates to the public for the very first time. Over 20,000 eager guests walked beneath the castle gates, each dressed in their Sunday best and ready for a brand-new adventure. 

Today, for many Disney fans worldwide, there is magic in recreating that feeling of excitement that guests felt on opening day. For some Disney fans, capturing the style of the 1950s era is one way to recreate that magic. To do so, guests from all over come together to celebrate a bi-annual experience that is uniquely Disney: Dapper Day.

What is Dapper Day? 

Founded by longtime Disney fan Justin Jorgenson, Dapper Day is an organization that celebrates the style of yesteryear by organizing events that encourage “stepping out in style” while visiting the Disney Parks. Greatly inspired by the trends of the mid-twentieth century, it’s a celebration of fashion and fandom delightfully meshed into one day. The name of the event is also a shout-out to the Dapper Dans, a popular pinstripe-suited quartet of gentlemen who dazzle Disney guests with acapella renditions of Disney classics in the Magic Kingdom.

When the unofficial event initially launched in 2011, around 100 people came to the California parks for a dapper afternoon. By 2017, over 25,000 people reportedly participated in the event!

When & Where is Dapper Day? 

While “Dapper Day Disneyland” originated in the Anaheim parks, Disney Dapper Day is now held at Disney properties on both coasts, although the festivities differ slightly. For example, there is an entire Dapper Day Expo in California at the Disneyland Hotel, which requires an extra admission ticket! In Florida, the two-day event is only in the parks (typically at Magic Kingdom and EPCOT), with some participants congregating at Disney Springs. There is typically one event in the spring, and another held during the fall, giving those who would normally visit the park just once or twice a year more opportunities to attend.

Spring festivities for Dapper Day at Walt Disney World in 2023 have already taken place, but you have plenty of time to start planning a super spiffy ensemble for the fall outing! This year’s fall Dapper Day is actually happening on the cusp of winter, on Saturday, December 2nd, and Sunday, December 3rd.

One major draw of Dapper Day is that the event does not require an additional ticket to attend. It’s an unofficial event completely unaffiliated with the Walt Disney Company. It’s wholly created by fans, for fans! There are no costs to attend or participate, unlike events such as Mickey’s Not So Scary Halloween Party or the Magic Kingdom After Hours.

Dapper Day VS Disneybounding 

Since Dapper Day emphasizes fashion, it can often be mistaken as an extension of Disney Bounding (or vice versa.) However, this is not the case – the two have very different concepts. Disney Dapper Day is an opportunity for Disney fans to showcase their love of retro fashion, often emphasizing the style of the ’40s, ’50s, and ’60s with a modern flair. Bright colors, suit jackets, and full skirts are staples of the day and are generally done with a Disney theme.

It’s a chance to doll up in your most posh attire and visit The Happiest Place on Earth with hundreds (or thousands) of like-minded fans. Vintage-inspired looks are the most popular, but you don’t have to perfectly re-create the outfit of a specific era. Fans simply let their imaginations run wild!

On the other hand, Disney Bounding is essentially just dressing up with a look inspired by your favorite Disney character or film.

Indeed, Dapper Day participants do sometimes choose to incorporate aspects of Disney Bounding into their outfits! After all, who doesn’t love to see a dapper Donald Duck? Or a stylish take on Minnie Mouse? The two concepts often overlap at these events. Ultimately, though, Dapper Day places far more emphasis on fashion rather than incorporating cosplay elements.

Stylish Tips & Tricks 

As Dapper Day gains popularity on the East Coast, you’ll find that many parkgoers flock to Walt Disney World for the spring and fall events. If you’re planning to attend a Dapper Day outing, there are a few things you should know before you go:

• Plan Ahead – You’ll want to arrive early and be prepared to wait. While the park doesn’t necessarily sell out on event days, it’s always a good idea to get your tickets in advance (and those Genie+ Lightning Lane services!) if you aren’t an Annual Passholder. The park is likely to be extra busy on Dapper Day, so be prepared to wait for any attraction you want to visit.
• Consider The Weather – Let’s face it, Florida weather is temperamental even in the best of times. It’s warm, humid, and rains frequently. Your attire should match the forecast to the best of your abilities. Many Dapper Day Disney guests incorporate parasols for sunny days or light jackets or umbrellas in the rain.

• Think About Style – What era are you considering for your Dapper Day look? Most park-goers choose a style from an era they like best, usually the ‘50s or ’60s. Others take a more Rockabilly approach to retro fashion, incorporating past eras with a more modern touch. You could even go steampunk! We’ve seen everything from adorable a-lines to elegant ballgowns gracing the parks. If you want to be really dedicated to dapperness, you can match your make-up style, jewelry, and hair-do with your era, too!

• Don’t Forget Comfort – While style is the name of the game, you can’t forget that you’ll have your snazzy outfit on all day at a theme park. Heels might complete a cute look, but they’ll also kill your feet, so you might want to opt for flats instead! If you’re planning on riding the roller coasters, think about needing to stow a stylish hat every time you board a fast ride. You could also find that your fancy hair-do will quickly come undone. Considering your park plans when you’re deciding on your outfit will help optimize comfort. That makes any day truly dapper!
• Be Flexible – As we’ve pointed out, the weather may not always cooperate with your initial idea for an outfit. To be prepared, consider a backup in case you find rain in the forecast as the event draws near.  You can plan to wear layers for the weather or have a secondary outfit picked out just in case!

• Photos! Photos! Photos! One of the major draws for Dapper Day in the parks is the opportunity for perfect photos with spectacular backdrops! You’re in The Most Magical Place On Earth, after all. You’ll want to show off your outfit! Official Disney photographers will be on hand to make the magic happen, but it might be easier to get that perfect shot if you come with friends. Be prepared to wait for the best spots, as everyone else usually has the same idea!
• Make New Friends – People travel from all over the world for Dapper Day. You’ll meet amazing, fashionable people from all over (and possibly even close to home!) on your visit. Don’t be afraid to share how much you appreciate their style or share your love of retro fashion with those you see. Dapper Day is an excellent opportunity to meet up with like-minded Disney fans. Everyone is there for the same reason, after all. You never know, you might meet your new best friend!
• Have Fun – The most important thing to remember during all this is simply to have fun! Take things at your own pace and enjoy the experience of Dapper Day 2023!

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Featured photo: Kevin Gaudin via Flickr