Dapper Day: The Complete Beginner’s Guide To Vintage Outings

in Disneyland Paris, Disneyland Resort, Walt Disney World

two people dressed in vintage fashions at a disney park

Credit: Dapper Day

Ready to step out in style? We’ve got the complete handbook to a vintage sartorial day at the Disney Parks with the Dapper Day crew!

We’re here to walk you through everything you need to know to attend, enjoy and celebrate Dapper Day at Disney. Build yourself an outfit, plan your discounted room, and feel the vintage splendor of opening day at Disneyland Resort. Let’s go!

What is Dapper Day?

dapper day 2021
Credit: DapperDay.com

Dapper Day was first conceived by its founder, Justin Jorgensen, in 2011. Justin arrived in Los Angeles, CA, from Fargo, ND, as an artist and designer looking for fun and refined style. Justin says, “we’re best known for producing events that let you “step out in style” at museums, parks, and other destinations,” when asked what a Dapper Day weekend is.

“I wish I could dress up without everyone looking at me.” That was my motivation behind our first event, an outing to Disneyland. I liked visiting Disney’s parks, they’re rich with attention to detail, color, and exquisite gardens. I also liked clothes, often very colorful clothes, and suits (also usually colorful). And this interest of mine would often draw unwanted attention wherever I went (which was usually by myself). So I needed to find more places where I could blend in with other “dressed up” people–or create those places myself. 

After meeting up with friends who wore more casual clothing for a trip to the Parks, the group saw a beautifully dressed couple who expressed discomfort with how they “stuck out” from the crowd. Justin sought to change that, and

“decided Disneyland should be the site of our first outing, and it would have to be in the winter as it’s more friendly to multiple layers of clothing, (and generally, the more layers, the better the look). So I put out the call and encouraged anyone who wanted to “step out in style” to join me for a day at the park, Sunday, February 20, 2011. I specified “dress up a little–or a lot!” and embrace contemporary fashion as well as vintage styles. The point was for everyone to celebrate their own style. Likewise, by not dictating a strict dress code or period, I hoped guests unaware of the event would notice a difference in how the park looked that day but wouldn’t be able to see a clear separation between those participating and those who weren’t. They would just notice the park seemed a bit more special that day. I wanted the boundary to be blurred, I didn’t want to create a dynamic of some people feeling part of a group and others being on the outside.”

Now, Dapper Day gives artistic and retro stylings a front and center seat for those looking to enjoy a day at the Disney Parks. Anyone can join in the fun!

Lindsey Dapper Day
Credit: ITM Reporter Lindsey Goodson Paris

Related: Fan-Favorite Spring Event Snubs Magic Kingdom for the First Time in Years

How Do I Attend Dapper Day?

Where do you want to vacation when “dapper-ing?” Dapper Day is held at Walt Disney World Resort, Disneyland, and Disneyland Paris, about twice a year. This means you can have more than six Dapper Day event choices to attend. Once you choose your destination, check the Dapper Day website, which will share updated lists of dates at each Resort, which Parks are to be visited on select days, and how to book your discounted room and tickets (if available). Oftentimes, the founders of the non-official Disney theme park event are able to block a selection of rooms at one or two Disney Resorts for a fabulous discounted rate. Be sure to book early – these events are popular!

Destinations like Disneyland Park often have a Dapper Day Expo to go along with them, and tickets may be required. Dapper Day participants can find more information about these specific outings on the Dapper Day website.

There is no age requirement to attend, meaning you can come solo, or bring the whole family for retro theme park fun. You will have to have a Park Pass Reservation and a ticket for destinations like Walt Disney World, so make sure to check purchase and attendance requirements at your Park. Children 2 and under do not require a ticket or a Park Pass Reservation.

What to Wear to Dapper Day

dapper day trio of minnie and mickey outfits
Credit: OhMyDisney

Oftentimes, coming up with specific inspiration can feel like a chore. Disneybounding combined with vintage or retro looks can be a bit challenging for beginners, considering there are so many elements to a proper Dapper Day outfit. First, we advise choosing a decade. While Dapper Day as a theme mostly refers to the 1950s, when Disneyland originally opened (specifically 1955), participants have been stretching the eras from the 1920s to the 1970s and making it their own.

Plenty of ideas for what to wear to Dapper Day are online, you just need to know where to look! This site offers looks from the 1920s all the way through the 1990s, though that’s a bit modern for a true Dapper Day outing. You can also search “Dapper Day outfits” and find plenty of past participants sharing their style. When composing an outfit, it’s important to consider period-style makeup and hair, which add emphasis to your look!

sunshine tree terrace with orange bird dapper day dress
Credit: redheadbabymama.com

Next, consider if you want to tie in Disneybounding with your look. Pulling colors from a Disney character (such as red, black, and yellow from Minnie or Mickey) can be helpful in designing an outfit. Disney Dress Shop dresses often already incorporate an attraction or character into the designs, doing a lot of work for you! While you won’t be able to wear a complete Halloween costume, Dapper Day allows you to be fanciful and bring a bit more character into your outfit!


Dapper Day is mostly about stepping out in style, taking photographs, and enjoying the Disney Parks. That means a lot of walking. Sensible shoes don’t typically match vintage looks, so you have to get creative. Proper insoles, socks/stockings, or extra flats are helpful. Some participants will carry a pair of dressy shoes for photos while wearing tennis shoes, flats, or other options during the bulk of the day. This writer recommends choosing something that covers both worlds, like Walking Company Saddle Oxfords, padded, colorful Keds, or simple flats with insoles that keep with your look.

Lastly, hair and makeup. Florida Parks can be very hot, while California Parks can be windy at times. Pack your bobby pins and hairspray, but also practice your updo, Barbie ponytail, or hairpiece at home before going on vacation. Bring spray fixative for your makeup, so you are photo-ready whenever you want to be!

What Do You Do At Dapper Day?

All dressed up and ready to go to the Dapper Day Events? The biggest tip we have for you is to ready your camera and your smile! People-watching and outfit-glimpsing are some of the best things about Dapper Day. The limitless creativity of designers, vintage rockabillies, and new dapper-ers is on full display. Visit the Disney PhotoPass Photographers for special magic shots, collect your own poses by Instagram walls, and document feeling fabulous for a day!

If you love attractions and rides, be sure to take in original opening day attractions for a special take on Dapper Day. Mad Tea Party teacups, carousel rides, and classic dark boat rides are perfect ways to spend the morning. Just be sure to bring a scarf for your hair when tumbling around Big Thunder Mountain Railroad!

If you ever need help planning a day of style at the Disney Parks, call on the professionals at Academy Travel. They have the knowledge to help you plan a vintage Disney vacation that you’ll never forget! Call them at 609-978-0740 today.

What do you love most about Dapper Day at Disney? Leave us a comment below!

View Comments (2)