Dapper Day. What is it? The first time we heard, or in our case saw, Dapper Day was at Disneyland Paris. When we were waiting in line to rope drop the park, we saw hundreds of guests dressed in 1950’s style clothing. We were very confused, and wrote it off as a European thing. About 6 months later, after joining the Disney community on Instagram, we found out what it really was.

Dapper Day is basically a day where parkgoers dress up in “vintage classics, to chic contemporary looks” in the parks. It was created in February of 2011 by LA Designer Justin J, to encourage stylish living from yesterday and today. Dapper Day is most well-known in the Disney parks. Guests from all over the world come to the parks on select weekends to dress up. Scroll down to the bottom of this article to see some of our favorite outfits!

When is it?

The next Dapper Day is on Saturday November 17th at Animal Kingdom (and later heading to Magic Kingdom), and on Sunday November 18th at Epcot. The best way to stay up to date with when Dapper Day is, is at the official website here!

There are special hotel rates at AK Resort, Pop Century, Port Orleans, Beach Club, Contemporary Resort, and Grand Floridian Resort. The rates are valid only for the Dapper Day outings, plus several nights before and after.

What to wear?

Dapper Day celebrates the tradition of “stepping out in style” and does not require you to dress in a specific time period! Any sophisticated style is encouraged.

Here’s a few of our favorite looks, worn by our friend Dawnmarie from the Enjoying the Days blog! From the pictures you’ll see that Dapper Day is meant for people of all ages! You’ll also notice that the same people are wearing multiple outfits. That’s because Dapper Day is a multi-day event, so there are outfit changes!

If you’re looking for more inspiration, scroll to the bottom of this article and check out our gallery.

Outfits for Women

Outfits for Men

Accessorizing

There’s more to an outfit than the dress or suit! You can see that Dawnmarie and her family accessorized perfectly. Dawnmarie carried vintage suitcases, wore big hats, gloves, and tights! Her shoes also completed the looks, but were still practical for the parks. (If you can wear heels all day in Disney, we applaud you. But if not, find a safe in between!)

Dawnmarie’s husband and her son each wore bow ties, an easy way to add a “dapper” look to an outfit! They also wore suspenders, colorful socks and suits, and hats.

Where to shop?

The best place to shop is thrift shops or a vintage specialty store. Our friend at the Disney Trivia Blog also wrote an amazing article about The Dress Shop, which has dresses inspired by The Tiki Room, Orange Bird, Mary Poppins, and more! Click here to read the article.

More Inspiration

We asked some of our friends to send us their Dapper Day outfits. Click on the pictures below to browse through the gallery! The outfits range from vintage inspired to Disney character bounding like Cruella, Carl from Up, and Scar!