Paula and Dawn pause in Tomorrowland

With all the fantastic, creative, and superbly dressed guests, you can’t help feel a little extra joy when it’s Dapper Day at the parks. The fan created event started as a day to visit Disneyland when people who enjoy dressing up for a day at the parks, could all be with others who share the same passion.

Dapper Day has since expanded to include other parks and resorts and even art museums. This weekend, it’s at Walt Disney World. If, like me, you love to see how creative people can be, Dapper Day is a great time to visit the park, even if you’re not inspired to dress up yourself.

Ciara & Nick had a really sharp 50s vintage vibe

Dapper Day’s creator was inspired by the early concept art by the likes of Imagineering greats Herb Ryman and John Hench for Disneyland and Walt Disney World, which always showed guests dressed in their finest when attending the parks.

Disney’s horticulture team had the park’s flower beds looking their best and the park also brought out a couple main street vehicles to act as backdrops. Of course, Disney’s Photopass cast members were extra popular today.

Although there are no rules for how to dress on Dapper Day other than ‘dress up’ (whatever that means to you). You have to follow the resort rules regarding costumes (and adults not wearing them). This means many adults tend to dress in what is called “Disney Bound,” where one’s outfit is inspired by a Disney character, attraction, or other iconic icon.

This year the trend was toward fasteners for women’s hair, handbags for both women and men, and some minor props to complete the Disney Bound effect.

I was also impressed with guests who came dressed to the nines whether it was Disney or not. Vintage looks from the 30s, 40s, and 50s are always ‘in’ in my book.

Thanks to everyone who agreed to take a photo for this article. I hope you may find some inspiration to dress up for a future Dapper Day event.

Dapper Day
Tara, Andria, Jennifer, Erin, Greg, Sara make up Pooh and his friends from the Hundred acre woods

Tomorrow Dapper Day participants will be visiting Epcot in their finest attire. If you’re a local, it’s not too late to start digging through your closet for an outfit.

If you missed the Spring event, another will follow in the fall (usually with cooler temperatures although today’s weren’t too bad as there was a light breeze).

You can learn about the next events, which are Fall 2019 at Disneyland and Walt Disney World on the Dapper Day homepage.