What is Dapper Day at Disney? (11 Tips to Make the Most of Your Day)

Dapper Day at Disney is just around the corner, are you excited?

If you have never been to any of the Dapper Day events at Disney, then get ready to learn about this super fun event at the parks.

Twice a year, Walt Disney World and Disneyland in California both celebrate Dapper Day. On these days, you are free to live out your life in the “poshest” way imaginable.

You can be all dolled up, looking prim and proper like a Southern Belle. But in an atmosphere filled with colors, laughter, style, and socializing.

THIS POST MAY CONTAIN AFFILIATE LINKS. PLEASE READ MY DISCLOSURE FOR MORE INFO.

Dapper Day Disney World People in front of PhillarMagic

Today I’ll go through all you need to know about this elegant, mid-20th century inspired event come to life at Walt Disney World.

What is Dapper Day?

Okay, so this guy, Justin Jorgensen, thought of this very dope idea about people coming together to celebrate styles from the past.

Kind of like a fashion show, but with everyone coming in as their own model at the show.

The idea saw the light of day in February of 2011 and has since evolved to one of the most anticipated gatherings where people showcase their inner fun and fashionable side.

The event is hosted at different locations throughout the world from hotels, museums, expo centers, and various Disney parks across the globe.

For a no obligation, FREE Disney Vacation Quote you can fill out the form with Destinations in Florida by Clicking HERE!

What to Expect from Dapper at Walt Disney World

Dapper Day at Disney World invites you to get lost in the most magical way as the colors, vibrancy, and elegance of the atmosphere make everyone, well, Dapper.

Dapper Day Disney World People in Fantasyland

The reason for the event is for you to step out into styles that best represents you. You’ll get the opportunity to meet other people, celebrate fun and flirty vintage looks, whether classic chic or contemporary looks that showcases your style.

Where is Dapper Day?

As mentioned earlier, Dapper Day is not only held in the California parks, but if you live near Florida and can’t make the trip to the West Coast, you can enjoy this one-of-a-kind event in the Orlando parks in both the fall and spring.

Where are all disney parks located with castle, epcot ball, hollywood tower hotel, and tree of life at animal kingdom.

Dapper Day Locations

  • Disneyland in California
  • Los Angeles County Museum of Art
  • Walt Disney World in Florida
  • Disneyland Paris in France

So, get ready to dress in your best retro outfit when attending the event.

Dapper Day 2014: Main Street USA in classic fashion with NikkyJ of ThemeParkHipster
Dapper Day 2014: Main Street USA in classic fashion 🙂

You don’t have to come looking like you are a guest speaker at a church event, but you can infuse some classic looks from celebrities such as Billie Holiday, Marilyn Monroe or Frank Sinatra.

When is Dapper Day at the Disney Parks?

Although the Walt Disney World Resort is the place that we’re going to focus on for today, the dates listed below are for all the events and expos taking place around the world.

Dapper Day 2019 and 2020 Dates at Participating Disney Parks

Dapper Day Disney World Tom Sawyer Island Fort with People Playing Checkers

Fall 2019

Winter 2020

Spring 2020

Dapper Day Disney World 2019 Dates, Events and Times

How to do Disney Hollywood Studios Solo
Hollywood Studios

Disney Springs

  • On November 14th and 15th from 5 p.m. to 7 p.m., you’ll get to meet the founder, Justin, of Dapper Day at Marketplace Co.

Hollywood Studios

  • On Saturday November 16th, enjoy the fall outing with other Dapper Day friends at Disney’s Hollywood Studios. Be sure to take some of the best photos in your poshest outfits in the beautiful Hollywood-themed areas.

Epcot

  • On Sunday November 17th, don’t miss out on the fall outing that will be taking place at Epcot during the Food & Wine Festival. Not only will you get to dress up in your favorite fashion, you’ll be able to get some awesome photos of the best international architecture inside World Showcase.

Dapper Day Pop Up Shops

  • Thursday through Sunday (November 14th – 17th), you can visit the Dapper Day Pop Up Shop at the Co-Op Marketplace in Disney Springs.
  • Friday through Sunday (November 15th – 17th), you get to visit the other Pop Up Shop located at Legends of Hollywood inside Disney’s Hollywood Studios.

Dapper Day Disney World 2020 Dates, Events and Times

Epcot Flower and Garden Festival one-day itinerary with colorful topiary.
Epcot Flower and Garden Festival
  • Friday, May 1st: Dapper Day Weekend Kick-Off (Final details pending)
  • Saturday, May 2nd: Spring Outing at Disney’s Hollywood Studios
  • Sunday, May 3rd: Spring Outing at Epcot

11 Dapper Day Tips

Now that we’ve gone through the basic information for you to know about this event, let’s go through the best tips to help you a great day while creating incredible memories with friends or on your solo trip.

Boat Hats for Men at the Magic Kingdom Disney

1 -Have a Few Dapper Day Ideas for Your Outfit

Dapper Day is all about having fun with a classy twist. Whatever you choose to wear to Dapper Day at Disney is totally up to you, but I recommend putting an extra little touch to your theme park outfit for this special occasion.

When choosing your ensemble, you should have a few options and ideas in mind.

Outfits of choice can come from any era, whether it is from the 1940s, 1950s, 1960s, or even an outfit from a classic Milan fashion show. The criterion is that it has to be very dapper.

For most people, Dapper Day evokes old styles or vintage charm. Whatever direction you take, you can use a few tips and ideas for your outfit.

Dapper Day Disney World Tom Sawyer Island Fort with People Walking

Dapper Day Outfit Ideas and Tips

  • Three-piece suit for the men with dark classic shape sunglasses and females with turn of the century garb similar to ones like the characters in the movie, Mary Poppins.
  • Choose an outfit that matches the theme of the Disney park you’re visiting. So for the Florida parks, think classic Hollywood for Hollywood Studios and retro chic for Epcot. At the Magic Kingdom, colorful inspirations from the earlier days of the 20th-century will be perfect for this park.
  • If you choose to do vintage, shop at the best antique stores in your neighborhood. Better yet, ask one of the older women in your family to lend you one of their dresses for the event.

Even with all of these tips for your outfit, remember that Dapper Day is just pure, lighthearted fun.

No one will judge you based on what you are wearing, but looking dapper does take a little bit of effort.

My best advice is to keep it simple if you’re not into fashion.

2 – Know the Types of Dresses to Wear

If you haven’t been to any Dapper Day event, it looks like a 1940s and 50s elegant ballroom party in the middle of the Walt Disney World magic.

The Haunted Mansion Wallpaper Dress for Women Official shopDisney
Classic Haunted Mansion Dress

Thinking of dresses can be difficult, but here’s a tip to help you out.

Pick a fashion year that speaks directly to your personality. If you pick the 1960s, you can wear dresses with an A-line shape and lots of pleats.

You can also go with your girls and choose matching dresses that represent the princesses or characters from your favorite movie.

Plus, you can dapper it up a notch by adding a certain decade to your princess garb.

Dapper Day Dresses

You will see a lot of vintage looks at Dapper Day in Disney, but you can add a modern twist to your dress with accessories.

Floral, monochrome, pleats, embroidery, and lace prints are all good choices to pick from for your look.

You can buy your handmade Dapper Day inspired clothing here on Etsy!

3 – Know How to Choose Your Hairstyle

Your hairstyle should be something simple, yet classic that best fits you, but the classic pinup hairdo is a popular style for the event.

Dapper Day Hairstyles

Dapper Day Hairstyles Ideas

  • Bold curls flowing on your neckline with combs holding the side in place
  • A tight bun towards your neckline with a part in the middle and a fascinator
  • Soft high, messy bun with floral accessories
  • For guys, a nice clean cut with a handlebar mustache

Either way, a hairstyle for as far back as the 1920s or other years will do for Dapper Day at Disney.

4 – Choose a Hat to Compliment Your Outfit

Finding the perfect hat for your classic garb is one of the fun things to do when preparing for this event.

Disney World Tom Sawyer Island Fort with NikkyJ

You will be astonished by the number of hats you can find for the Dapper Day experience at Disney World.

Plus, you’ll be able to choose from little ones to really big, extravagant hats that include a variety of accessories.

Dapper Day Hats

Hats are a key part of what make your Dapper Day outfit complete. If you don’t like hats, have a simple hair accessory.

Dapper Day Hat Ideas

5 – Choose Comfortable Shoes

I always choose style over comfort, but for Dapper Day I try to combine the two as much as possible. For you, I recommend having a nice outfit with flat business casual dressier shoes that have cushion.

Disney World Shoes

But whatever makes you happy and dapper, do it.

Just remember that you’ll be doing a lot of walking around to get your epic photos and you may not have too much time to rest your feet.

However, if you feel comfortable rocking a six-inch heel, by all means, do you! 🙂

Remember that comfort is essential to bringing your style together. Flats, short heels, straps, or even sneakers are great choices.

Just be sure to match your shoes with your outfit and accessories to make them pop.

6 – Plan Out Your Day

Disney Springs Freebie
Disney Springs

Review the schedule for the weekend. This year’s Dapper Day in Disney World is a three-day event that kicks off in Disney Springs where you’ll get to meet with the founder of Dapper Day, Justin, and other participants of the weekend.

Remember to pack as you would on any vacation with all your necessary documents, clothing, self-care items before you head to Disney.

You’ll also want to go over the park maps to get you familiar with the layouts.

7 – Take Lots of Dapper Day Photos

The best thing, besides dressing up at Disney, is taking photos in your unique outfit at some of the best theme parks in the world.

Best tips for the Magic Kingdom
Magic Kingdom with Friends on Dapper Day

Whether you’re using the PhotoPass system with a Cast Member, or giving a stranger your smartphone, get as many photos as you want for the duration of the event.

Plus, it’s a great memory to have from your Disney trip.

8 – Plan to Arrive Early

This is a classic tip for any theme park trip. Especially if you want to see and do everything during your visit.

Tom Sawyer Island Dapper Day at the Magic Kingdom
Tom Sawyer Island

Coming early to Dapper Day will give you a chance to pace yourself by allowing you to enjoy all the activities special of this event.

If you have plans to be at Disney before it starts, you’ll want to book a room on property or close by to be able to get to all the activities quickly.

Learn how to find your perfect vacation home rental near Disney World by Clicking HERE!

9 – Check the Weather

Since Florida is filled with more hot, humid days than Disneyland in California, you’ll want to dress for the weather.

This may take away from your outfit, but if you come prepare, you’ll be fine. The fall Dapper Day outing is the best because the weather is usually perfect.

Waiting for pics at the carousel in Fantasyland
Dapper Day 2014: Waiting for pics at the carousel in Fantasyland

However, the Spring outing can be hit or miss as the heat begins to kick it up a notch in preparation of the tortuous summer season.

If you do decide to come in the Spring, then make sure that you take lots of breaks indoors to prevent any overheating.

You can read how to beat the heat at Disney here!

10 – Socialize with Other Dapper Day Participants

Dapper Day is a great way to meet new people and make connections. So, don’t just hang out with your own group, start a conversation with other participants who are just as dapper as you.

Disney World Tom Sawyer Island Fort with People Standing Around

If you’re a bit shy, a great conversation starter is to compliment someone on their outfit.

Since you know how challenging it is to prep your outfit, you should understand that letting another person know just how good theirs is can lift their spirit.

11 – Have Fun!

You’re going to have so much fun, so don’t stress on all the small stuff. Just show up ready to take lots of photos and ready to meet wonderful people!

A fun fact about Dapper Day is that it’s not associated with the Walt Disney Company. It’s purely a fan based event of vintage inspiration that was started in 2011. Dapper Day has grown to bring in over 10,000 participants across the Walt Disney World Parks in Anaheim, Orlando, and Paris in the spring and fall.

What to Know Before You Go

Now that we’ve went to all the tips for your special day. Let’s go over a few frequently asked questions.

Dapper Day Disney World Magic Kingdom with woman smelling white flowers

What Is Dapper Day All About?

As mentioned early, Dapper Day is all about people showcasing their retro fashion sense in a fun and unique way with others just as dolled up for a great time at Disney.

Do I Need to Register to Partake in The Event?

No, you don’t need any form of registration. The Florida location currently does not have an Expo attached to it like the one in California.

Disneyland California Where are Disney Parks Located

If you do visit the Florida event at any of the Disney Parks, then you will need a park admission ticket to participate.

Please note that Disney Springs does not require you to pay since it is an outdoor shopping and entertainment area.

Is There an Age Restriction for Dapper Day Events?

No, the event is for everyone – children and adults alike. If you want, you can even bring your grandmother along.

It is about style, personality, and fun.

Are Costumes Allowed Considering the Disney No Costumes Rules?

Costumes are NOT ALLOWED at Disney parks.

Dapper Day is a chance for you to enhance your normal theme park wear into something more stylish and classic.

Epcot Dress for Women Official shopDisney
Get your own Spaceship Earth Dress here on the Disney Store!

Can I Bring Food Into Disney?

Yes, you can.

I recommend that you bring yourself some light snacks and water to help your get through the daily activities.

Hollywood Studios Tower of Terror Ride at Disney's Hollywood Studios looking eerie
Hollywood Studios Tower of Terror Ride

Final Thoughts

Dapper Day is a fun-filled day for everyone to dress their best and enjoy the Disney enchantment. The event in Florida promises to be the best experience for everyone who loves fashion, good people, and Walt Disney World.

So, come show you Disney side in your best style, all the while dancing, socializing, and taking pictures on your magical day. After all, it is Disney where the true magic happens.

This is a ThemeParkHipster approved event!

What is Dapper Day at Disney World
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Have you ever been to Dapper Day? If so, let us know in the comments section below.


If you enjoyed this article, then you’ll love these:

Read the Disney Vacation Planning Guide for your next dream trip!

Until next time, Happy Park Hopping Hipsters!

NikkyJ

(Original Article Date March 11, 2014: Updated 10/31/2019)

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