Groovy Dapper Day Planning

The Final Countdown

I can't believe Dapper Day is just around the corner.  Tracy and I take off on Thursday, November 16th, and that is only 19 days away!  That means it is time to buckle down and get organized, no matter how busy I am at work.  In this post, I'm going to talk about how I choose my outfits, and how I organize all the details.

Many of us love to plan our Disney trips, sometimes down to the minute, with Dining reservations, park shows, fast passes, and more.  Even if I have it all in My Disney Experience App, I still like to write it all down.  I personally always include a daily outfit planner to go along with my reservations and plans, that way I can wear the outfit most appropriate for that day.  This couldn't be more important for Dapper Day trips, you certainly don't want to forget to pack some of those special touches like brooches, hair accessories and jewelry.  It's all in the DETAILS!

Photo by Stephenie Lodermeier 

Photo by Stephenie Lodermeier 

Themed Fashion 

A lot of people ask how I choose my outfits and themes for Dapper Day.  There are so many incredible outfits at Dapper Day, sometimes it seems daunting to start from the beginning and pick something.  I choose to dress up my everyday Pinup/Rockabilly look every single time I step into the parks whether it's Dapper Day or not, so on the ACTUAL Dapper Day itself, I really love to challenge myself to take it to the next level.  But I encourage everyone to dress however they want to flaunt it!  Dapper Day is often mistaken as a DisneyBound or specifically 40's/50's event, it is officially NEITHER, but instead an event created to inspire guests to go all out in fashion trends of all eras.  

Since fashion is the true heart of the event itself, I save my Disney Bounds for the days surrounding Dapper Day, and instead choose more of a  theme, ride, 'land', or movie for my outfits on those days.  It allows me to be more creative instead of trying to make literal representations of characters.  My favorite way to Bound, is to put a fun twist on an existing character, perhaps from a particular era, a mash up, or fashion trend.  Last year, Tracy and I put a vintage twist on a bound as Peter Pan and Captain Hook on the day before Fall Dapper Day 2016.  Expect some fun character interpretations on this years Fall trip as well! Did someone say Tiki?

Peter Pan, Tink and Captain Hook, Fall 2016

Peter Pan, Tink and Captain Hook, Fall 2016


Making my list, checking it thrice...

I've got my days all mapped out, themes and bounds picked out, even some of my outfits, shoes and accessories, but what's my outline for making sure I'm not leaving some important items behind?

Here's the LIST I created to ensure I've got it all packed:

  • Date and Name of Park Visiting, i.e.: November 19, 2017 (Sunday) EPCOT 
  • Outfit/Theme 
  • Top Garment
  • Bottom Garment
  • Fascinator or Hair Accessories
  • Petticoat
  • Shoes
  • Purse
  • Accessories, Jewelry

So far, this checklist hasn't let me down!  What would you add to this list?  Do you still have a lot to purchase or finish making before Fall Dapper Day?  I have most of my outfits, but I still have lots of special touches to complete, plus a couple small garments.  

Fall Dapper Day 2016

Fall Dapper Day 2016

No matter what, make sure you have an AMAZING time at Dapper Day!  It doesn't matter if you don't wear something outrageous, what does matter, is that if you want to participate, come down to the parks, and join us for what I certainly believe are the most magical days at the parks, we're all happy to have you as company and share these special days!  

Hope to see you on Main Street!