A Beginner’s Guide to Dapper Day

Next to Christmas – and maybe my birthday – Dapper Day is my favorite day of the year! What is Dapper Day? Dapper Day is an event that celebrates “stepping out in style” in the Disney Theme Parks. There are events held in the spring and autumn at Disneyland, Walt Disney World, and even Disneyland Paris! Everyone is encouraged to wear their Sunday best, just like guests did when visiting Disneyland in the 1950’s. Sounds fun, right?! Last April I had the opportunity to get “dolled up” and experience Dapper Day in Walt Disney World’s Magic Kingdom!

Here are my top tips for attending Dapper Day:

Don’t be afraid to go all out! Don’t be scared to look “silly.” You will see people dressed in true vintage style. I’m talking vintage clothes, vintage shoes, and even vintage hair and make-up. If you want to go all out, go for it! I applaud you! If that’s not your thing don’t worry, there will be plenty of ladies wearing simple sundresses.

Shop for your outfit at local vintage stores, thrift stores, or flea markets! Not only does this promote local businesses, but you can find some great one of a kind pieces that no one else will be wearing. It’s every ladies’ nightmare to show up to an event and see someone else wearing the exact same thing as you!

Choose outfit that will compliment what you want to do! Make sure what your wearing is practical and comfortable enough to do everything you plan on doing in the park. Let’s be honest, petticoats and Space Mountain don’t go together very well. Riding the carousel, I had a difficult time getting up on my horse in my little wiggle dress. So if you plan on riding lots of roller coasters, please make sure to hold your skirt down!

Wear comfortable shoes! No matter how cute those pumps are, after several hours in the heat and humidity you will have some blisters. If you do insist on wearing heels, bring a pair of flats with you to change into. The ladies I went with wore adorable white tennis shoes!

Take lots of pictures! There are TONS of photo opportunities in Magic Kingdom some of which include: Main Street USA, Main Street Rail Road Station, Prince Charming Regal Carousel, Cinderella Wishing Well, the “purple wall,” and countless Disney characters and princesses . . . am I forgetting any where? OH Cinderella’s Castle!

Be appreciative and humble of the attention! I arrived late to Dapper Day. When I was riding the monorail to Magic Kingdom, I received A LOT of curious glances. Many people don’t know what Dapper Day is and will ask you why you’re dressed up. Some older ladies complemented me for dressing up but many people just blatantly stared at me. Always say “thank you” to everyone that compliments you! I saw a group of gals roll their eyes at a young boy who said they looked pretty. So please, always be humble when someone has the courage to come up and compliment you.

Want to experience Dapper Day for yourself? Contact Hallie, your Dapper Travel Advisor, for more information!

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