Disney Dapper Day Tips + Video of Dapper Outfit Ideas

Thank you for sharing!

Spring Dapper Day 2016 was my very first Dapper Day. Dapper Day is an amazing event that is held at Walt Disney World, Disneyland, and Disneyland Paris.  

It started as a way to pay homage to the way people used to dress when they came to Disney. They dressed in their best: pearls, heels, and bow ties! My first Dapper Day didn’t go exactly how I would have liked it to have gone, but I am sharing with you my Dapper Day tips so that you don’t make the same mistakes I did.

I am getting ready for Fall Dapper Day 2019 so I thought I would update this post to add even more Disney Dapper Day tips and share with you some Disney Dapper looks to get you inspired!

Disney Dapper Day Inspiration Video

Disney Dapper Day Tips

Unlike other Disney events, Dapper Day is not a ticketed event. This is because Dapper Day is not Disney ran but rather Disney approved.

Plan your Trip

The dates for Dapper Day are announced about 9 months ahead of time. That gives you plenty of time to plan your trip. If you are coming from more than 2 hours away, it is best to stay overnight before and after Dapper Day. The official Dapper Day Site offers a Discount on your stay, but that is subject to availability. Click here for more information.

If you are staying on property, make sure to get your Fastpasses at your 60-day mark. Passholders and those staying off property can book Fastpasses at the 30-day mark!

Though there are some scheduled photo opportunities, you are free to do whatever you want.

Get dining reservations 6 months out, especially if you are wanting character dining to go with your outfit.

Plan Out Your Outfit

What Do You Wear to Dapper Day?

You can wear whatever you want to Dapper Day. Dapper Day is not a particular fashion era, just a day of dressing your best. You will find that most people dress in outfits inspired by older generations. I usually wear circle skirts and outfits that remind me of the ’50s.

Men Get Dresses Up Too

Don’t forget to have your men and boys get all dressed up as well. Though I see lots of guys sport a 3 piece suit, I think it is usually a bit too warm for that even during the fall Dapper Day Weekend. A nice shirt with a tie or bowtie is the most common comfortable look I see.

Dapper Day Run Through

I had a rough idea of my outfit but didn’t try it on and put it all together until the day before. I wish I would have. I was running around the day before picking up certain items and then forgot to pack some of the items. It is a good idea to do a Dapper Day run through. Try on your outfit, shoes, accessories, practice your hairstyle, and even do your makeup. Lots of gals do retro hairdos and makeup. I do not.

Where to Buy Dapper Clothes

Petticoats – If you are looking for a nice, well-made plus-sized petticoat, Malco Modes make some great ones! They also sell regular women’s sizes. Malco Modes make the fullest and fluffiest petticoats.

Dresses – Popular sites to buy Dapper Day dresses include Amazon, PinUp Girl Clothing, Torrid, Cherry Tree Lane Dress Shop, and ModCloth. Thrift shops are great places for finding a dress since they have a lot of retro items.

Bow Ties – Etsy is a popular place for Bow Ties, especially ones that may be Disney themed.

Be Prepared For All Weather

It may rain, it may be blazing hot. Make sure you have accessories for each. Parasols and hats help with the sun. Umbrellas help with the rain. I have made the mistake of not putting on sunblock. It was cloudy for most of the day and then the sun came out. It was out long enough to burn me good.

Wear Comfortable Shoes

Many people wear heels to this event. Many props to those who do! This plus-sized princess couldn’t deal with that. I wore tennis shoes. If you want to wear heels or dress shoes, please make sure to have a backup pair of comfy shoes to switch into for later in the day.

My friend, Millie, has “photo shoes” that she wears for photos and then switches to more comfortable shoes while walking around. She is so smart!! You can also buy a pair of cheap canvas shoes from Walmart and paint them to look like saddle shoes– comfy and retro!

Meet New People at Meetups

The Dapper Day page lists a general timeline. I went to the People Mover and River Boat “meet up” in 2016 and it was pretty amazing to see so many Dapper people all doing the same thing. There are lots of Disney fans pages that host little meetups and I am a member of the D3 Darlin’s which had a few fun photo opps.

Make New Friends

During my first Dapper Day, I was so scared to meet new people. I spent most of the day alone, just watching everyone else having fun. I am so glad that changed when I started to hang out with the D3 Darlins. Some of my best friends are my Dapper friends. Say hi to people you don’t know. strike up a conversation with another Dapper dressed friend in a line, and most importantly smile.

Prepare for Wardrobe Malfunctions.

Wardrobe malfunctions can and will happen. Bring an emergency sewing kit and safety pins so you have what you need to fix a stuck zipper, lost buttons, or anything else that may come your way.

Have Fun!

This is what I did do right during my first Dapper Day. I had a blast! I enjoyed the compliments. I enjoyed people watching. So many people Disney Bounded, it was amazing!

When is the next Disney Dapper Day?  

Here are the dates for 2019 

• Sat, Sept 28 DAPPER DAY Fall Outing to Disneyland Paris
• Sun, Nov 3, DAPPER DAY Fall Outing to Disneyland CA
• Sat+Sun, Nov 2+3, DAPPER DAY EXPO at The Disneyland Hotel
• Sat+Sun, Nov 16-17, DAPPER DAY FL Fall Outing (Specific parks TBA)

Walt Disney World Special Offerings During Dapper Day

Special Merchandise – Disney usually has a special pin, though it does not say Dapper Day. It is usually a Disney couple all dressed up.

Special Photopass Opportunities – Disney embraces Dapper Day even though they don’t run it themselves. Each year tends to be something different. Spring Dapper Day 2018 they had the Main Street Vehicles out a bit more than usual and they had one specifically for a special Photopass picture.

PopUp Shops – Cherry Tree Lane Dress Shop and PinUp Girl usually have a Dapper Day area in the park.

Have you been to Dapper Day before? What Dapper Day Tips do you have to share, let me know in the comments!

This article was originally published on May 6, 2016.

Looking for more Disney Fashion?

• Buzz Lightyear Dapper Disneybound
• Beauty & The Beast Dapper Disneybounds
• Cherry Street Lane- Disney Dapper Dresses 

Thank you for sharing!