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What is Dapper Day at Disney World?

What is Dapper Day at Disney World?

If you were enjoying the parks two weeks ago, did you ask yourself why are those people all dressed up? Or did you think to yourself, man I feel incredibly under dressed even though I’m just walking down Main Street or strolling around World Showcase. Well, you were smack dab in the middle of Dapper Day at Disney World!

What is Dapper Day at Disney World?

First, what does Dapper even mean? Dapper refers to dressing smart or neat. Dapper Day celebrations are still relatively new to the Disney parks whether here in Disney World, Disneyland, or in Disneyland Paris. Not just for adults, but families (mine included) really get into the fun. A man, by the name of Justin Jorgensen, came up with the idea in the winter of 2011 to make a fun group event where everyone could dress up and enjoy Disneyland in California. Even though it was put together pretty last-minute, the idea caught on fast, so he decided to make a fall Dapper Day event. That is where the twice a year celebration of stepping out in style truly began. Fun fact, despite being held at Disney parks, it has nothing to do with the Walt Disney Company.

Check out their website for the latest information. Make sure to add your email to the mailing list, so you can get the inside scoop like special non-park events (they have a lot in LA) or neat pins (you know I’m on that email list). You can also follow them on Instagram and Twitter. As far as the schedule goes, the next weekend at Disneyland CA will be Nov. 3-4 2018, and Walt Disney World will be Nov. 17-18 2018. It will be slightly different this fall in Disney World compared to recent years. They’re splitting up Saturday, November 17th. The morning to mid-afternoon (3 pm) will be at the Animal Kingdom, and then at 5 pm, the fun will start at the Magic Kingdom. I will say it has been nice with the one park per day, so we’ll see how this new change will go over. My hunch is, after this time, they will go back to the one park a day LOL!

Where to Start if you Want to Attend Dapper Day

So now you’re thinking, hmmm this seems like a lot of fun and want to get all gussied up, but don’t know where to start?! Don’t get stressed about thinking it only belongs to a particular era. Dapper Day embraces all vintage fashion from 20’s flapper to 70’s disco plus everywhere in between. I will say this spring (Disney World), I saw a lot more twenties inspired outfits compared to this past fall. The weekend was kicked off at the Edison at Disney Springs, so that may have set the tone for some outfits. At Epcot, one of my favorite flapper-inspired looks was a whole group who “assembled” as the Avengers. On the other hand, I embraced the 50’s Rockabilly style for the parks and 40’s for the kick-off event. As you can see from the pictures below, I like to go all out and have a lot of fun.

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At the kickoff event, I will admit my dress was SUPER last-minute (unlike months of thought behind my poodle skirts) because I was supposed to see the Avengers with my son, but my hubby came home early from a work trip. I did my hair and makeup too and felt pretty proud of myself.  Saturday, my husband and I had such a great time as 50’s sockhop Woody and Bo Peep from Toy Story. Talk about a fantastic date strolling through the Magic Kingdom as our favorite characters. A cast member thought our outfits were so cute that she gave us free snacks at her ice cream cart (of course I opted for a Mickey ice cream bar hehe)! I will say my husband wants to dress up even MORE for the fall (but doesn’t want to help in the planning LOL). On Sunday at Epcot, I met up with friends as Cruella de Vil. Boy oh boy, it was a blast being evil for the day. To me, it’s fun playing a character like that.  But you don’t have to create your look from a Disney character either. Most people we saw were just in beautiful retro ensembles.  A classic look is always in style!

Where to Buy a Dapper Day Outfit

Personally, I have great ideas but can’t execute AKA I can’t sew to save my life. If you are like me, a great resource (where I got my dress for the Edison) is Rent the Runway. RTR offers a lot of fabulous vintage-inspired dresses for all budgets, and the rental process is so simple. A very talented friend of mine created my poodle skirts. I bought the circle skirts off Amazon, and then my friend did the applique based on the designs in my head. The tops I found from Goodwill (another great place to find hidden gems)! Amazon is an excellent choice to find Dapperesque dresses and accessories ( crinoline, bow ties, and suspenders) for pretty cheap. If you are in search of a more custom look, check out Etsy. Then there’s always the Cherry Tree Lane Dress shop at Disney Springs for theme park and movie inspired dresses.

The pictures below are from the Fall 2017 Dapper Day events (orange bird dress from Cherry Tree Lane and purple & black flower dress from Amazon). I learned a lot from our “first time” last year. Don’t wear my hair down (your style will last longer up), and don’t wear an outfit that requires heels! I’ll be rocking the 50’s sockhop vibe for a while haha! Another great tip, to make sure your makeup lasts use a really good setting spray. I like Urban Decay All Nighter. Having a cute parasol and little fan also add to your ensemble and help keep you cool! But most importantly, we learned how much we LOVE this event! The wonderful thing about Dapper Day is you can dress up as much or as little as you want. Your ensemble can be a part of a group with friends or solo. Don’t forget you can always go to people watch. You know I am already planning our November looks!


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Are you planning on attending any Dapper Day events? Will I see you in November? Post in the comments below!