Dapper Day

*cue Rapunzel voice* I’ve been dreaming about this my whole life and I am going to see those vintage dresses!

…Or at least the past three years, since I’ve known what Dapper Day is.

For those who are still in the dark on Dapper Day, it’s a designated day in which fans of Disney and fans of vintage collide to create some awesome outfits and commemorate what it used to be like when the park first opened in 1955. Back then, it was a treat to go to Disney (as it still is today) and people would dress in their Sunday best for an outing in the park. There’s usually a fall and spring Dapper Day, both in Disney World and Disneyland to maximize the number of people who can join in the celebration. I’ve never been able to go because it’s normally right in the middle of a school semester, so when I was accepted into the DCP, one of the first things I did was look up when Dapper Day would fall so I could request it off as soon as I was given access to do so.

I learned about Dapper Day through DisneyBounding one night my freshman year of college when I was obsessively scrolling through Leslie Kay’s blog. My personal style is more t-shirts and running shorts just because I’m too poor for anything else, but if I had time and money, I would love to think my style would be inspired by the 1950’s. The rockabilly look is so classic and vintage makeup is something I aspire to be able to put on my face one day, so this seemed like the perfect way to test it out. A combination of Disney and vintage things? A true dream come true.


Unfortunately, my look wasn’t as great as I wanted it to be for two reasons, the first because I had been going on two weeks of bronchitis by the time Dapper Day came around in April. (It was a REALLY fun three and a half weeks in Disney…pro tip: don’t get sick during your DCP, you’ll never fully recover.) The second was because of the dress itself. I ordered it online from some random website I found through Google and I’m pretty sure it came from somewhere in Asia. I spent WEEKS searching for affordable vintage dresses in either light blue (for a Cinderella look) or light purple (Rapunzel) and I finally settled with this dress. The style was great, but the website’s sizing chart said the dress ran small so people should order 1-2 sizes up. I also hate shopping for clothes, but especially online because I can’t try it on and there’s no guarantee that it’ll fit. So I’m usually a small or medium and decided to order a large because if something comes in and it’s too small, there’s nothing you can really do about it, but if you get something larger, you can always pin it. And boy, did I pin this dress. After all was said and done, I probably had about 10-12 safety pins in this dress trying to shape it around me. If I get to participate in another Dapper Day, I’m absolutely finding something that I can try on before committing to it so I’ll be more comfortable throughout the day.

But aside from being sick and in a dress two sizes too big, I still had a great day.  There was a huge DisneyBound meet up so everyone who had a Disney-inspired vintage outfit on could get together and appreciate each other’s creativity.

I’m towards the left, about four rows of people back. You can see my head right behind the older lady in the red polka dot dress and head piece. Such a beautiful group of people to admire and it was so cool to be a part of!


Plus, it’s always good when your twin sees your look (yes, two different times) and loves it. Rapunzel was amazing that day (even though she probably saw 500 other Rapunzel look-alikes) and she loved my tsum tsum Pascal.

This sweet Rapunzel brought extra pins with her and when she saw me walking around with my Pascal, she offered to pin him to my shoulder! He sat there happily the rest of the day.


Not to mention, Cinderella fixed my hair when a flower fell out of it and I completely freaked out on the inside (and maybe a little on the outside).


Speaking of the hair, let me tell you those victory rolls were a bitch. I used probably half a can of hair spray and there were probably about 7-8 bobby pins in each roll. Oh well, I tried.

But the hair was worth it when Leslie Kay asked how I got my hair to stay so well in the rain/humidity and she said she would need tips for the Disneyland Dapper Day that was happening about a month later. Once again, I completely freaked out and fangirled over how nice she was. (Are you sensing a pattern here?)


Not only was it my first Dapper Day, but my first time eating at Be Our Guest! At lunch, it’s a quick service place and it’s definitely easier to get a reservation for breakfast and lunch than it is for dinner. Shelby and our grandma joined in Dapper Day too since the next day we were all running the Star Wars Half together.


I also think it’s worth mentioning that I twirled dresses with Rapunzel and it was everything I hoped it would be. The video I have of us twirling and talking is probably one of my favorite memories I have from my program.

I wish I could have stayed longer and taken some sunset pictures, but the next day was the Star Wars Half and I had a 3:00 alarm set for the following morning. I already knew I wasn’t going to sleep that much because of the aforementioned bronchitis, so I was trying to take it as easy as possible before going out and running 13 miles.

I would HIGHLY recommend participating in Dapper Day on your DCP! You’re already there and you don’t have to model your clothes after a Disney character—it’s just about dressing to the nines and having a fun day in the park with everyone else who’s in on the secret.


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