I became a Cast Member in 2013, but I don’t remember anything about Dapper Day before the spring of 2014. That’s okay, I also didn’t know what Disneybounding was until right before I moved. Don’t worry, I’m going to explain Disneybounding later in this article if you don’t know what it is. My first experience with Dapper Day involved a fourteen-hour shift at the World Famous Jungle Cruise, and one of my favorite memories as a Cast Member. (That is a story I’m saving for the newsletter early next year, so subscribe now if you haven’t already!)
Dapper Day is a semi-annual event held at both Disneyland and Walt Disney World, and once a year at Disneyland Paris. The event began in 2011 in California and rapidly grew in popularity. The idea is that you come to the parks in your “Sunday Best”, essentially how it was originally envisioned the guests would dress coming to Disneyland in the 1950s and 1960s. Your dress doesn’t necessarily need to be vintage, just stylish. The events are not actually put on by Disney themselves, though they have gotten more involved as the event has grown. In Spring 2016, the last Dapper Day I attended, Disney didn’t officially have anything special for event. Spring 2017, they had special cupcakes, corsages and all sorts of things. Fall 2017 was a little different, as something else was overshadowing Dapper Day.
Last year, they started making Walt Disney World’s Dapper Day a two-day event, but I only planned on doing the Magic Kingdom day.
Somewhere along the line as I was planning out my year, I realized Day One of this year’s Dapper Day would fall on Mickey Mouse’s birthday. I immediately knew I wanted to theme my Dapper Day outfit around my favorite incarnation of the Mouse, the Sorcerer’s Apprentice.
Enter Disneybounding. Disneybounding is the idea of theming your outfit around a certain character. Created by Leslie Kay, Disneybounding has quite the following on Tumblr. Since anyone over the age of twelve isn’t allowed to wear a costume to the Disney Parks, this is how many people find ways to still be their favorite character. I wish I Disneybounded more often, but it typically calls for a lot of solid colors and most my clothes already have Disney characters printed on them. However, for Dapper Day this year, I knew I would be Disneybounding Sorcerer Mickey.
I hunted around online for a 1950s style red dress that I liked, not fully sure how I was going to make this work until I stumbled across one particular design. I literally recolored it in Paint since the computer I was on at the time didn’t have Photoshop and sent it to my friend Polly. She’s an awesome costumer and has been helping me with projects (and occasionally keeping me sane) since 2010. You can check out her blog, $20 Lolita, where she talks about making Budget, Offbrand and DIY Lolita clothing. I know we talked about her putting the dress on it at some point, but as of publishing I haven’t seen it on there yet.
My outfit was settled, Duffy would wear his sailor outfit, and now it was time to figure out Jay’s. I originally wanted him to go as Steamboat Willie, but he thought it would be a little boring, but also look strikingly like his Gangster outfit from Mickey’s Not So Scary Halloween Party. I agreed on at least the second point, and we spent the day before the event hunting for an outfit for him. At JC Penny inspiration struck, and Jay would soon be the Yensid to my apprentice.
The morning of Dapper Day, my alarm went off at 3:50 a.m. If you’ve ever paid attention to my photos, you might have noticed I have all of three hair styles, and on the rare occasion I wear make-up, it always looks the same. Our friend Victoria was kind enough to agree to do my hair and make-up for Dapper Day, but she had to work at 7:30 a.m. This meant I had to be at her house at 5 a.m. Well, I overshot by half an hour and she did an amazing job anyway.
The Disney Parks Blog had been advertising a special moment in the Welcome Show for Mickey’s Birthday, and we made it just in time. However, I should have known not to get my hopes up. The “special moment” was literally the Squire saying, “Happy Birthday, Mickey!”
Now that the park was officially open, we popped over to ride the Haunted Mansion. Then it was time to hit as many characters as possible: Alice, Merida, Ariel, and Snow White all before 10 a.m. I carried my heels between characters and switched into a flimsy pair of flats that folded up to fit in my bag.
We tried to go to Storybook Circus, but apparently, they don’t open until 10 a.m. these days. After Snow White, we waited in the twenty-minute-or-s0 line for Starbucks because we were both badly in need of caffeine, and more importantly, I had a gift card. I saw the special Steamboat Willie Cheesecake on display, but decided that much sugar so early in the morning would likely spell disaster and we grabbed pretzels at the Hub instead. While we were in line for the pretzels, a girl who was not Dapper, but covered in Duffy from head to foot caught my eye and I probably stared longer than was polite.
At the entrance to Liberty Square there are benches on either side. We grabbed one and sat down to eat our pretzels. We wound up sitting there people watching for about half an hour, checking out all the Dapper Day outfits as they went by. Other dressed up guests would smile and nod or wave, and some even called, “Happy Dapper Day!” Shortly after we sat down, “Mickey’s Friendship Faire” started and we could see about half the stage. I’ve seen the show countless times, but I love the music so we stayed until the end.
We went to see the pop-up shop at Box Office Gifts for the official Dapper Day merchandise. The creator of Dapper Day was there, Justin Jorgensen, and I wanted to get a picture with him but it was busy and hectic, and I wound up deciding not to bother him. It was really cool to see the clothing in person, even if it was out of my price range.
Nine times out of ten, if I’m walking up or down Main Street, I cut through the Emporium. It’s air-conditioned, there’s no sun, and you never know what you might find. In this case, someone found me. The girl with the Duffy stuff spotted me again, and came up to introduce herself. Turns out she’s a blogger too! We traded business cards and she gave me a little folded up piece of paper of Duffy! As small and simple as it was, it was probably my favorite part of the day.
One of the many great photo spots we found.
When I originally planned our Fastpasses thirty days in advance it never occurred to me we would be there for park open, so none of our Fastpasses were until the afternoon. At least this left us with a nice, slow morning to take our time doing what we wanted. We wandered around the park a bit looking for fun photo spots, and had to abort one location just as we arrived because Joey Quintin had posted where he was doing his first button giveaway on Instagram, and I didn’t know how quickly he’d run out. Joey is an amazing artist I encountered at MegaCon, and he was doing button giveaways for Dapper Day. The line was super long when we got there, and I didn’t expect to have so much pressure as I picked our buttons. I froze, and later thought of four other designs I would have rather picked. Oh well. They’re still wonderful!
We went back to Storybook Circus to find Minnie and Daisy’s line at forty minutes and Donald and Goofy’s at twenty-five. We picked the boys since meeting Daisy is always awkward for me anyway. (She took Duffy’s spot at Epcot, I’m still bitter.)
After the Circus, we went to ride the Carousel. Well, I rode the Prince Charming Regal Carousel. Jay stood on the outside and took pictures. Riding sidesaddle is strange, and I’m a little surprised the Cast Members allowed it.
Finally, it was time for our first Fastpass and we made the extremely short, about twelve foot, trip to Princess Fairy Tale Hall. We jumped in the line for Rapnuzel and Tiana, and everything was going great until we were done. I went to switch back out of my heels to the flats when I felt something come undone in the dress.
The zipper had gotten stuck that morning, and we’d used a couple of safety pins to close it under the belt. Jay went to check, and sure enough the safety pins were now all bent and useless.
“I don’t know how to fix this,” Jay said.
“I think I do.”
I headed over to Bippity Boppity Boutique. Who better to fix a wardrobe malfunction than a Fairy God-Mother in Training? I explained the situation to Corley and she immediately went running off. She came back with a handful of safety pins and a few rubber bands. Jay and I popped over into a gift shop so he could repin the dress, and everything was good as new in no time!
We headed over to get in line for Winnie the Pooh, and there was no one there. He’d be back in half an hour, so we sat down on the wall to wait.
I don’t think I’ve ever had a Photopass Photographer take so many photos. There were twenty-four of them when we were done! Pooh took Duffy from me, and wanted to keep him, but I said no. Then Tigger was mad he wasn’t getting any attention and pulled me to dance while Jay and Pooh conspired to hide my Duffy Bear. Needless to say, I got him back before we left and some amazing photos.
It was finally time for our Mickey Mouse Fastpass, and we were both exhausted. Jay was breaking in a new pair of shoes, and my flats were so thin I might as well have been barefoot. We decided to skip our last Fastpass after 5 p.m. for Cinderella and Elena, and make seeing the Birthday Boy our last stop. We swung over to Pecos Bill to get the Steamboat Willie Cheesecake with my annual pass discount, only to find them sold out. I got them to check the other venues in the park offering it, everywhere was sold out. I was more disappointed than I probably should have been. I love both cookies and cream, and cheesecake! Jay was right, we should have just gotten it at Starbucks that morning.
When we got into the room to see Mickey, he wasn’t there yet and the character attendant got everyone to sing him “Happy Birthday” as he came in. It was adorable! The line was moving super quick and it was our turn in no time. There will never be a day I’m not excited to see Mickey Mouse, and I’m so glad I got to tell him “Happy Birthday!” in person.
We headed for the monorail and made our way out of the Ticket and Transportation Center, eager to get home and dump the photos from my camera.
Dapper Day is an awesome time, and one of the few special events at Walt Disney World that doesn’t require a separate admission ticket. This was the second year I’ve gotten to do it, and I hope to be doing it again in the future. Sadly, both the Spring and Fall events fall in the same month as RunDisney races, and there’s only so many weekends I can take off at a time. I think I like the Spring event better just because the Christmas music was majorly throwing me off and the decorations on Main Street made photos a little more challenging.
I do already have plans for another outing with my dress, but it will be sometime next year at the earliest.
Cost: Park admission.
Value: I have a harder time scoring the value on this one because it’s not something you pay for, but I definitely think it’s something every Disney fan should do at least once!
Duration: All day.
Add Ons: You could do both days, or they had an event at Paddlefish on Friday this time at Disney Springs. According to the Dapper Day website, they have more expansions planned for Walt Disney World!
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