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Steppin’ Into Style for Dapper Day | Walt Disney World

It’s no secret, I love Dapper Day a lot. A lot, I mean, I could have a problem. But since Dapper Day doesn’t come around again for another 6 months, I’m going to cure my Dapper Day blues by telling you all about why this is an incredible event that is only getting better.

Dapper Day, Dapper Day at Disney World, Dapper Day Weekend, Dapper Day Dresses, What is Dapper Day

Dapper Day is for EVERYONE, not just Disney Bounders, not just vintage lovers, you don’t have to be super knowledgeable of any particular fashion trends, it is just an opportunity to experience the beautiful parks we know and love in a new way! I have been lucky enough to attend the last 3 Dapper Day weekends at Walt Disney World, and each one has been better than the last.

Recap the Unique Experiences at Spring Dapper Day

Friday Night – Cocktail Reception at BOATHOUSE Orlando at Disney Springs

Dapper Day’s official welcome party is always an excellent opportunity to meet new friends and catch up with others from Dapper Day’s past. The Dock is always a beautiful space to socialize and snap some pictures.

Dapper Day, Dapper Day at Disney World, What is Dapper Day, Dapper Day Dresses

Disney really showed their love for Dapper Day by offering special Dapper Day discounts at the DS Starbucks, and free mini makeovers at MAC and Sephora. They even had special PhotoPass opportunities in the Marketplace, so of course, we had to take advantage!

Dapper Day, Dapper Day at Disney World, What is Dapper Day, Dapper Day Dresses

Saturday – Dapper Day at Magic Kingdom

Once again, Disney showed their support for the weekend by having Disney florists selling corsages, flower crowns and more near the entrance to Main Street, and hosting a ‘The Dress Shop at Cherry Tree Lane’ Pop Up event with Dapper Day’s founder, Justin. But it didn’t stop there, they were offering a Picnic Lunchbox to eat on the Hub Grass with some tasty fried chicken and some adorable Dapper Cupcakes! Once again, they added some unique PhotoPass opportunites including having the Main Street Transportation vehicles out and about on Main Street and in the Hub.

Dapper Day, Dapper Day at Disney World, What is Dapper Day, Dapper Day Weekend

Sunday – Dapper Day at EPCOT

After having a Dapper Day event at EPCOT in the Fall of 2016, I think everyone knew it was going to have to continue to occur. EPCOT is just such an outstanding backdrop for photo opportunities, food, socializing, just about everything in my opinion.   I was happy to see another event at EPCOT and look forward to continuing to have them there in future. The private event at The Living Seas Lounge is really lovely for those of us who really love the vintage garb and socializing in amazing air conditioning. I’m a big lover of Pinup Girl Clothing, and having a few minutes to chat with Pinup royalty like Doris Mayday certainly makes it even better.

Dapper Day, Dapper Day at Disney World, What is Dapper Day, Dapper Day Weekend, Dapper Day Dresses

Dapper Day, What is Dapper Day, Dapper Day at Disney World, Dapper Day Dresses, Dapper Day Weekend

The Pinup/Rockabilly Style is something that I do everyday whether at Disney or not, but that doesn’t mean you have to be like me to participate or ‘do it right’. We all have a fashion palette that is constantly changing and at Dapper Day, just BE YOU! That’s the best part.. and of course, take lots of pictures!

Dapper Day, Dapper Day at Disney World, What is Dapper Day, Dapper Day Dresses

This post was written by Guest Blogger, Jeni, is a fellow Disney blogger, Chicago restaurant owner and Disney fanatic.
Find Jeni on Social Media:

Instagram | Blog | Dia De Los Tamales


Monday 15th of May 2017

I've never heard of dapper day but you look amazing! I would love to take part one day.


Monday 15th of May 2017

So I never heard of dapper days!!! I lived in Fl for a million years too. I love anything themed so I'm sad I never experienced this!!!!

Elizabeth O.

Saturday 13th of May 2017

I am not aware of Dapper day! I think it's a lot of fun to be able to dress up and just have a good time. It's really nice! It's definitely something to look forward to.


Saturday 13th of May 2017

Dapper day looks so awesome! I've always loved that Rockabilly style but I never know if I can pull it off or not. Y'all look good!


Saturday 13th of May 2017

This looks like so much fun. definitely something I will want to participating with my girlfriends !

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