Dapper Day Do's and Don'ts

What is Dapper Day? UM, IT’S THE BEST. Do you like dressing up? Do you like Disney Parks? You are going to love it! It’s for Disney fans of all ages, it takes place twice a year at Walt Disney World, Disneyland, and Disney Paris, and it doesn’t cost anything (other than your standard park admission, or if you want to participate in the VIP events.) 

Let’s do a little recap of outfits and then we’ll go over some Dapper Do’s and Don’ts, shall we? Above is my first ever Dapper Day, with my handsome husband!  

Left is my Disneybound of the tightrope walker stretching portrait in the Haunted Mansion; right with my vintage Pan-Am bag for the first ever outing at Epcot.

Left, a tiki nod to my favorite resort: The Polynesian. Right, a Haunted Mansion look. (Are you sensing a theme? Or a disquieting metamorphosis?) 

So really, what do you DO at Dapper Day? 

DO: Dress to the nines! Take advantage of the opportunity and go all out. Some attendees are vintage mavens and pinup models everyday, some would normally be in jeans and a t-shirt. Whether you want to wear a historically accurate 1920’s flapper dress of your own creation or the same 3 piece suit Justin Timberlake wore to the Grammys is up to you.


DO: Make friends: I’ve been to Dapper Day with a group of people, and I’ve been by myself. I’ve met up with people I only knew from the internet, and I’ve hung out with friends that I made at previous Dapper Days. Making new friends is hard ay any age, but at Dapper Day you have a built-in ice breaker. “You look great!!” People come from all over to participate, plus most people love discussing their outfits and are happy to pose for photos. 

(Left photo by Sean Neumayer

DO: Prepare yourself: As you’ve probably guessed, it is hot and sweaty in central Florida at all times of the year. Combine that with a fancy outfit and dressy shoes…you’re bound to have some struggles. You can always bring a comfortable change of shoes (clock the flip flops above) a vintage fan or parasol, but my personal MO is to always plan on Dapper Day being laid back- it’s not really the time to check off every ride on your bucket list. It’s nice to just meander the parks at a reasonable pace, enjoying the scenery, atmosphere, and meeting other fabulously dressed folks. 

DON’T: Wear a costume! Not only is it against Disney park regulations, it’s not in the spirit of Dapper Day. Per the website "DAPPER DAY events celebrate sophisticated dressing and timeless style from yesterday and today. We want to see your personal style at our events. There’s many other opportunities to wear a costume or cosplay. DAPPER DAY events are meant to feature you being you!" If you really want to be a character, you can opt to Disneybound- choose your color scheme and accessories to reflect the character while still maintaining your own personal fabulousness.  


DON'T: Be a grump! Even though Dapper Day is growing bigger year after year, most guests at the park won’t know what’s going on and will be coming up to you periodically to ask. Share with them! In fact, share with everyone- there’s enough Dapper love to go around. And don’t forget to profusely thank and be kind to every cast member you see. It’s a really crowded weekend (akin to a Holiday) and they’re working hard to make your experience magical. 

…and that’s about it! It really is just that simple: Dress up, go to the parks, make friends, have fun! And yes, my bestie and I dressed as everyone's cult favorite Flower & Garden Festival beverage: Violet Lemonade. And yes I re-wear headpieces. (I made them!) Have you ever been to Dapper Day? Tell me in the comments! Or holler at me on Instagram, I'd love to take a photo with you. 

Note: Some of these photos were taken by the official Dapper Day photographer my lovely and talented friend Stephenie; who is California based but available worldwide.