There’s nothing more exciting than putting on your Sunday clothes and heading to Dapper Days. Although this year’s celebration looked a little different than last year’s, we’re celebrating the essence of the experience by sharing how we planned last year’s trip. Hey, it’s never too early to start planning for next year, right?

Where to Stay

There are so many choices and things to consider when planning out which Disney resort you want to lay your head down in after a long day in the parks. However when it came to our Dapper Day trip we knew we wanted to do something special. We also wanted to take advantage of the convention rates offered through Dapper Day (I’ve linked the Fall options here; note that they also do a convention rate on tickets). We also knew that we would be spending at least one full day at the Magic Kingdom only and would be ending our second day at EPCOT. All of this lead us to choose Disney’s Polynesian Village Resort. An added bonus of the Polynesian is that none of us had ever stayed there before, helping us to achieve our goal of staying at every Disney resort property. While we chose to stay at the club level for this trip (you can read about our experience in this post) the Polynesian has several other less expensive offerings. We loved how we were able to wake up and take the boat over to the Magic Kingdom first thing in the morning which allowed us to avoid long security lines and get our magic on at a record pace.

What To Wear

Shirt: Hot Topic, Skirt: Banana Republic

Choosing what to wear was probably the most difficult part of planning our trip. We had four friends in our group and knew we wanted to participate in both Dapper Day outings. We knew we wanted to do two different looks, which meant we had to get creative. While some people attend Dapper Day in elegant outfits that truly are their Sunday Best clothes, we wanted to put a Disney Bound twist on our outfits. We thought long and hard about Disney groupings of four before realizing that we were going about planning this all wrong! We decided our outfits would instead be an ode to our favorite place on earth: The Magic Kingdom. Each one of us dressed as one of the four main lands: Amy was Adventureland, Andrea was Frontierland, Megan was Fantasyland, and Allison was Tomorrowland. It took a lot of creativity and online shopping to pull together all of these outfits (huge shoutout to Amazon for providing each of us with at least one part of our outfits) but we were so pleased with our final products. We also felt it was important to be somewhat comfortable in our clothing, as we planning on opening and closing the park that day. We honestly don’t know how some of the people we saw did it in heels all day!

For our second day we decided to throw it back and dress like the original Mouseketeers. Part of the fun of Dapper Day is dressing how you would have visited the parks when the first opened. Keeping that idea in mind we decided this idea would be cute, fun, and easy to put together. We found our red skirts at Kohls, we all already owned white sneakers (and ears), and a friend screen printed our shirts for us. We of course had to go visit the boss man himself in our outfits, and although he didn’t say it, I think he was pretty impressed.

Final Thoughts

Thinking about attending Dapper Day? Here’s some other miscellaneous thoughts

Start planning your outfits early and try everything on once you get them! Megan’s skirt ripped right before we left for Florida and we had to do some emergency prime shipping to Andrea who was leaving on a later flight than the rest of us. It’s always a good idea to pack a back up!
Theming is fun! We got so many compliments on our “Four Lands One Park” Looks. While we did see other Mouseketeers, we didn’t see anyone else with our Day One outfits. They also garnered compliments from cast members which made us happy!
The comfortable shoes were worth it! While we have nothing but respect for those who wear heels in the parks on Dapper Day, that wasn’t for us. Our bodies aren’t what they used to be and so that means a comfortable sneaker is a must for our park enjoyment
Don’t be intimidated! There are so many incredible outfits online for Dapper Day, but it truly is an incredible experience. Visiting the parks on these two days remains one of my favorite memories due to the sense of community and togetherness that emerged seeing so many people from so many different walks of like all together celebrating this fun and positive event.

Have you been to Dapper Day? Sound off in the comments and let us know!