FashionEarsta’s Guide to Dressing for Dapper Day 2020

It’s almost here! That magical weekend where Walt Disney World is suddenly a swirl of petticoats, bow ties and parasols. That’s right: Dapper Day is imminent!

Dapper Day at the Parks, Spring 2015, Magic Kingdom, WDW Florida

If you haven’t heard of this event or, perhaps, have navigated through crowds of meticulously-dressed guests at Hollywood Studios and thought “are there open auditions for the Dapper Dans today?” allow me to explain. According to their website, this is an event first held at Disneyland resort in 2011. Dapper day outings to museums, events, and theme parks “celebrate the tradition of “stepping out in style” and are meant to showcase you looking your best while celebrating your own personal style.”

Dapper Day at EPCOT, Fall 2019

The Fall 2020 Dapper Day event at WDW will be held November 20-22!

After the cancellation of Spring 2020’s event due to the pandemic, and with Disneyland’s Fall Dapper Days very much up in the air, the fall outing to Disney World is sure to be the highlight of most vintage Disney fans’ social calendars!

And, yes, mid-November is a full three months away. Why are we talking about Dapper Day now?

Well, if you are a fan of vintage style, you understand how loooooooooong it takes to organize an outfit that makes you look like the cat’s pajamas. An extraordinary amount of work goes into crafting a dapper dress or other attire, so if you plan to attend or to celebrate Dapper Day at home, you’ll want to give yourself plenty of time!

One of Sarah Donawerth’s vintage dresses – she’s sourced some lovely accessories and that takes time!

Plus, with Disney World’s current advanced reservation system, you’ll need to book your park reservations now! (We’ll be at Hollywood Studios on Nov 21 and Magic Kingdom on the 22nd.)

The FashionEarsta staff is going all in for this fall’s event, so be sure to check back in November to see what we’re wearing! Plus I’ll be at the parks for the weekend to snap photos of my favorite outfits and creative, vintage takes on Minnie Ears!

But before we can get to that, I thought I’d share a little Earspiration for possible Dapper Day looks!

“Where Do I Even Start?”

There are so many possibilities for dapper outfits that it can be overwhelming to plan for these events! So here’s a few tips to get the ball rolling.

  1. This isn’t a Halloween Party, so no costumes allowed!
    • While this event is all about dressing up, we still have to abide by Disney’s “no costumes for adults” rule, so the fun challenge is to be inspired by some aspect of Disneyana without actually replicating character costumes.
  2. If you’re not sure, try Disneybounding.
    • Think about your favorite Disney character, film, or park attraction. Can you take a color scheme, pattern, or recognizable accessory from that inspiration and translate that into a vintage look?
  3. You don’t have to dress like a character, either!
    • Plenty of people take this opportunity to rock a vintage look that has nothing to do with Disney! It’s just fun to dress up, and there’s no pressure.
  4. Everyone is welcome, no matter their sewing skills, budget or level of commitment to wearing crinoline in 90 degree heat.

Earspiration: Dapper Cinderella(s)

Because “stepping out in style” isn’t constrained to a single time period, there are so many ways that you can rock a Dapper Day look. Disney World itself has a very 1950s aesthetic, so many participants choose a mid-century style. But get creative!

Here are a few vintage takes on my favorite Disney princess, Cinderella!

Art Dress Headpiece Wrap
Art Earrings Top Hair Flowers
Model Hat Lipstick Cape
Shoes Headband Necklace

My Etsy shopping cart is getting full of vintage accessories and clothing pieces, so I should stop myself here! Putting together a Dapper Day look is one of my favorite parts of the year, as you can see from some of my past choices.

So have fun! Play with items you already own (the middle look, inspired by Peggy Carter, was put together with items entirely from my mother’s closet!) and don’t be afraid to get fancy!

I hope this helps you get in the mood for this fashionable and fabulous fall outing! If you need any advice (or the name of a great seamstress) I’m just a comment away! Let me know in the comments below, or on our Facebook, Pinterest, or Instagram pages!

Pixie dust and glamour!

The Fancy Floridian


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