Dapper Day

It’s Dapper Day weekend, and, unfortunately, this will be the first time my husband, Wes, and I will be unable to attend since 2016. So in lieu of attendance, I thought I’d celebrate here with memories and photos of Dapper Days past.

Wondering what Dapper Day is? Allow me to explain. Dapper Day is a bi-annual weekend-long celebration of “stepping out in style” at the Disney theme parks. If I understand the original intent correctly, it pays homage to years past when people dressed up to go to theme parks. Dapper Day attendees often wear styles inspired by by-gone eras, but they don’t have to. The general idea is to just get dressed up and treat the outing as a special occasion.

For Wes and I, it has become our version of cosplay. The event is an opportunity to get creative. We choose Disney characters—usually couples because we’re gross like that—and try to determine how their costumes would best translate to a fashion style or era. Let’s be honest, what actually happens is: I describe and draw something absolutely atrocious; Wes interprets it, adds his own touches, and sketches something brilliant; then, Wes makes it (and I help when I can) because he’s really the talent of this operation.

Let’s get to the looks, shall we?

*Affiliate disclosure: As an Amazon Associate, the author may earn commission from qualifying purchases from Amazon.com.*

ANNA & ELSA – Epcot – Fall, 2016

Inspired by their coronation-wear, chosen because we already had fabric that would work for the Anna ensemble.

CHIP & DALE RESCUE RANGERS – Magic Kingdom – Spring, 2017

Wes created the prints for my dress and his shirt using Spoonflower. Definitely one of my favorite looks. I felt like Lucille Ball.

STAR-LORD & ROCKET – Epcot/DHS – Spring, 2017

Day two, and the only time we managed to go both days of the event. These characters seemed the perfect fit for Epcot’s “futuristic” ‘80s vibe.

ROBIN HOOD & MAID MARIAN – Magic Kingdom – Fall, 2017

Another one of my favorites. I wanted a dress like Little Edie Beale’s (of Grey Gardens fame) when she was in Life Magazine. The faux wood purse was an Amazon find that we painted to create the tree carving like in the movie.

WINNIE THE POOH & PIGLET – Magic Kingdom – Spring, 2018

I still can’t get over how cute this turned out! I wanted it to look like we were a 1950’s high-school couple, complete with a “pin” as if we were going steady. Wes reworked a sweater from Amazon and added the “P” patch.

CINDERELLA DOLL – Magic Kingdom – Fall, 2018

This was based on the Cinderella fashion doll that year, and I felt like a real-life doll. I felt silly (and warm!) wearing a wig, but I am a disaster with hair and knew I’d never get the style right.

WOODY & BO PEEP – Epcot – Spring, 2019

We ordered the prints for Wes’s jacket and the jacket linings from Spoonflower. If you can’t tell, we use that website A LOT. Wes made the purse from scratch. Do you see it? Is it giving you sheep vibes? This was my favorite look, for sure.

ARIEL & ERIC – Disney’s Hollywood Studios – Fall, 2019

The Little Mermaid has a very special place in my heart. Also, it was the perfect look to wear to Hollywood Studios. Notice the picture of us in front of The Voyage of the Little Mermaid show? Best show on Disney property. The pillbox hat, pearl purse, and Wes’s suit were all purchased on Amazon.

And that completes this dapper stroll down memory lane. Hopefully, we’ll be able to attend in 2021 with new and exciting designs! I highly recommend attending Dapper Day sometime if you haven’t yet. It’s so lovely to be part of such a creative community of people, and it’s fun to see what everyone steps out in.

It has also been great for Wes as an artist. A good deal of his work for our Dapper Day outfits inspired him and helped him reach a career goal: designing for the Disney Dress Shop. I’ll probably brag about him and his achievements with that in another post.

If you’d like to participate in Dapper Day this weekend but can’t make it to the parks, “Dapper Day at Home” will be featured on social media. So, put on your fancy clothes and share some pictures! Also, visit DapperDay.com for info on upcoming events!

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