What is Dapper Day at Disney and Should you Plan to Go?

Saturday was my first time attending Disney’s Dapper Day at Walt Disney World. I’ve been seeing pictures of this event for years and was so excited to finally see what it was all about. Dapper Day is one of several unofficial Disney events. Meaning Disney Parks has no involvement in the organizing of it, and it’s all handled from an outside group. As these things tend to do, Dapper Day has grown over the years since it’s start in 2011. They have an official website with all their events and FAQs. They organize fashionable outings to Disney Parks twice a year (spring and fall) in LA, Orlando, and Paris.

What is Dapper day?

According to their website, Dapper Day events “celebrate the tradition of “stepping out in style” and are meant to showcase you at your best. We do not aim to recreate a specific period. All sophisticated attire is encouraged from vintage-inspired classics to chic contemporary looks.”  Basically, retro and vintage clothing with a dressy look is encouraged but not to be confused with cosplay and costumes. This is actual clothing that you could wear anywhere. You do see a lot of Disneybounding, which is also real clothing but inspired by Disney characters. I chose to loosely Disneybound as Marie from the Aristocats since it worked with items I all ready owned.

The Spring event for Disney World was held at Magic Kingdom which I feel is the perfect backdrop for this style. The amount of photo opportunities is limitless! There were several group photo ops planned throughout the day as well. I was really surprised by the amount of people who attended. Main Street as well as the hub area was filled with Dapper dressed people.

Should you plan to attend Dapper Day?

For locals this event is a no-brainer. It’s ideal for us who go so often, and would enjoy new and different experiences in the parks. For out-of-town guests it’s not so sure. Due to being dressed up, you won’t be touring the parks like you usually do. Many rides will be difficult to go on, and your level of comfort with a large amount of walking will be tricky. I saw many, many people leaving with very sore feet. If you are here for one week and want to see and experience as much of Disney as possible, this day won’t be very productive. Increased crowds also mean the lines for things are longer and the hub area in particular stayed pretty crowded compared to normal.  For most people the day involved riding a few calmer rides, posing and taking pictures and chatting and visiting with other Dapper Day guests. Just the time is takes to be present for a large group shot can eat into a large portion of your day. So for infrequent guests to Disney World I would say to skip this event. For people who come often, and relish the idea of a unique Disney experience I think it’s fabulous! I would definitely recommend you attend at least once and absolutely dress up. If you are a big fan of this style it’s a must do. If you are a photographer or enjoy Disney photography as a hobby than this is a dream event. You will love the pictures you will get and the unique opportunities to connect with other Disney fans.

Overall I must say the thing I liked best about Dapper Day was seeing everyone else dressed up. No matter what size, age, color people were, everyone looked fabulous and they knew it. They strutted and primped and posed for pictures like celebrities. It was a wonderful thing to see and be a part of. Now that I’ve been I’ve learned a few things that I’d like to share with you if you plan on going to the next Dapper Day or anytime in the future.

Serena’s Dapper Day Tips

While style is everything, comfort must still be considered. Even if you aren’t running around the park riding everything like usual, there is a tremendous amount of standing and walking. There aren’t a ton of places to sit and rest. High heels may look the most glamorous, but they may not be worth it. I saw many people brought flats to wear and planned on changing into the heels for pictures, but honestly pictures are happening constantly and changing back and forth will get old. Not to mention that many people found flats or low heels that looked fabulous with their outfits.  Sore feet can be a deal breaker. Wearing clothes that are too tight or very warm are also not a good idea. If you are very uncomfortable, you will be grumpy. You will look grumpy in the pictures and won’t enjoy the day. So be comfortable and enjoy yourself.

If you are a little hesitant to go dressed up, try connecting with a group and going or meeting up with them. There are several Facebook groups that are great for this. In the one I like, Dapper Darlins many who were going by themselves arranged to meet up with others. It makes the experience more fun and makes posing and taking pictures easier too.

Bring things to touch up your makeup and hair during the day. Florida weather is unpredictable and heat, wind, and rain can do a number on your look. Also consider bringing a fan or umbrella for the heat. It actually wasn’t super warm this weekend which was nice, but it’s more usual that it will be hot. So things to keep cool are helpful, and fans and umbrellas can add an interesting detail to your look as well. On that note, don’t forget to stay hydrated. It’s easy to get busy and forget then find yourself feeling sick and head-achy in the afternoon.

Don’t be afraid to approach people and say hi, ask to take their picture, or just complement their look. People are super friendly and I never had anyone respond negatively. Also, this is a day that many Disney social media people are out and about. Some that you may recognize. If you see them don’t hesitate to approach them and say hello. Two of my good friends are recognized quite often when we go to events. Corinne, who works for Inside the Magic and also has a hugely popular Disney Instagram account called DisneyLifestylers, and John who has a big following on YouTube with the Big Fat Panda Show. In observing them as they walk around, I can see that there are some people who recognize them and aren’t sure whether to say anything. You definitely should! They love meeting people, and there’s nothing more flattering than having someone say they enjoy your work. So say hello, ask for a selfie, and have a great moment. I got a bit shy when I saw Leslie Kay, the creator of Disney Bounding- who I love and have followed for years. But Corinne dragged me over when I hesitated. So if all else fails, hang out with a friend who will do the same for you. I’m so glad she did and I would have been kicking myself if I hadn’t met her. 🙂

Feel free to ask any other Dapper Day questions in the comments below. Are you Instagram? Make sure you follow me to see the latest pictures from my days at Disney. They get posted there first. And click on any of these pictures to see them full size:

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