Feeling Fancy at Dapper Day at Disneyland

Many of us regular Disney visitors eventually come up with bucket lists for new things to try on future trips. Mine includes staying at every resort on WDW property, attending all the dessert parties (because yum), and eating at every restaurant in World Showcase at Epcot; from Canada to Mexico. Well, happily, one of our bucket list items got checked off last November when we traveled out west to Anaheim, California and attended Dapper Day at Disneyland. This has been a dream of mine since I learned about it and we finally got to attend!

Dapper Day is an unofficial event at Disneyland, Walt Disney World, and Disneyland Paris held in the spring and fall each year. The event centers around “fun, refined style from yesterday and today” according to the official website for the event. While many people choose to dress in vintage fashions, the organizers of Dapper Day state that “our DAPPER DAY events celebrate the tradition of ‘stepping out in style’ and are meant to showcase you at your best. We do not aim to recreate a specific period. All sophisticated attire is encouraged from vintage-inspired classics to chic, contemporary looks.” Therefore you’ll see looks from about the 20’s through today. Many attendees go one step further and “Disneybound” which is to take characteristics of a Disney character and represent that character through fashion, using colors and accessories, as opposed to a blatant costume or cosplay (which is not allowed for visitors over 14.)


We started planning our outfits as soon as we booked our hotel room (here’s a hint-if you plan on attending Dapper Day, you qualify for discounted hotel rates as well as discounted tickets!) I’m really not good at Disneybounding so I took that pressure off of myself right away. I purchased a Mary Blair-inspired dress from Pinup Girl Clothing, an online retailer specializing in retro looks, and started watching YouTube videos about pin curls, victory rolls and other period hair styles. After a trip to the thrift store, I had pearls and a vintage-style purse to accessorize my look . Amazon and Old Navy came in handy for the husband’s look, and the child who hates dresses agreed to wear one just for one day. With all our looks taken care of it was time to plan our trip. I got an insanely good deal on flights by checking the fares obsessively. I arranged transportation to and from John Wayne airport and booked our second hotel. We would stay at Disneyland Hotel for 3 glorious nights thanks to the Dapper Day discounted rates, and move to a Harbor Blvd hotel right across the street from the parks for the next 4 nights. We purchased 5 day parkhopper tickets so we could see and do everything without rushing, and I made reservations for a whale watching tour and rental car for our one non-Disney day.

There really isn’t anything specific planned at the parks for Dapper Day, but the Dapper Day expo takes place at the Disneyland Hotel and we were so excited to check out all the stuff! There were dozens of vintage clothing retailers, a barber, jewelry, pins, hair accessories, even a swing band and a dance floor for folks to show off their results from hours of swing dance lessons. The real fun starts once you enter the parks and get to see all the amazing looks that people have put together. The most fun was getting about a million photos taken by all the Photopass photographers in our dapper duds. We started the day at California Adventure for pictures, which was much more subdued than Disneyland that day. We then headed over to Disneyland for even more pics, people watching and parades.

Top Photo credit: Craig Berry via Flickr

Bottom Photo credit: Brandon Postal via Flickr

Dapper Day was such a fun way to kick off our first Disneyland trip and we made such great memories that day. We only hope we can attend more events like this in the future (in Paris, perhaps?) If you like to dress up in fancy clothes or Disneybound, we highly recommend you put Dapper Day on your bucket list!

What’s on your Disney bucket list? Have you ever been to Dapper Day? We’d love to hear about your experience in the comments!

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