What to Wear to Disney Dapper Day; OOTD

Attending Dapper Day 2013 at Disneyland Resort was kind of a spur of the moment thing. I had wanted to go after learning about it a month ago, but without an annual pass it wasn’t really an option. Finding an outfit was difficult. I am not much of a themed dresser and dressing from the 1950s or 1920s was difficult without the proper wardrobe. I also don’t experiment with hair and makeup often so it required some research to figure out how to create a look from the 50s. I tried to keep my makeup simple, white eyeshadow and winged black liner. During this period, a lot of women wore red lipstick. I feel that bright red ages me, and I don’t own red lipstick. So I opted for Β a pink lip instead.

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My approach to my Dapper Day Β outfit uses separates to create a look that is modern without losing its dapper-esque feeling. By taking trendy separates I can deconstruct this outfit to wear with items I already have in my closet. This means I am saving money by not buying a “costume” and recycling it to wear with other pieces I already own.

This is my first time at Dapper Day. I think I mastered a solid attempt at my first try at it. I decided to take modern trendy pieces and put together an outfit of the day that can be split up and worn separately with jeans, boots, blazers and heels.

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Blue Skirt – Cotton On – $13

White Button Up – EXPRESS – $15

Mustard Buckle Flats – Thrifted – $2

Hand Bag – Singapore -30 SD

Skinny Teal Belt – Banana Republic – $15

Bracelet – Alex and Anni – $23

Scarf – Flea Market in Sicily – 1 Euro

Total: around $100

Dapper Day has a lot of women dressed in polkadot sweetheart neckline dresses, A-line silhouettes, and men in bow ties, vests and newsboy caps. Even though I wore flats my feet were killing me by the end of the day. At the beginning I saw women strutting around in their kitten heels like it was nothing. By the time dinner time hit I noticed a lot of hobbling, limping and strolls instead of struts. Dapper Day is not for the weak. It was amazing to see all of the different outfits and with the music playing in California Adventure I really did feel like I was in a different decade. There should be more theme days at Disney. I would dress for them all.

If you are planning on attending Dapper Day in the future I have provided a few photos of what other, more dedicated dapper people wear.


Christina and Friend

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Tools to the perfect Dapper Day classic 1950s look:

Dapper Day Makeup Tutorial

Dapper Day Hair Tutorial

How will you interpret Dapper Day 2014?

6 thoughts on “What to Wear to Disney Dapper Day; OOTD

  1. Pingback: Calling all Disney Fashionistas, It is almost Dapper Day at Disneyland | The In Between Girls

  2. Pingback: Comic-Con Civilian;OOTD | The In Between Girls

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