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 a pink lip instead.
My approach to my Dapper Day 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.
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.
Tools to the perfect Dapper Day classic 1950s look:
Dapper Day Makeup Tutorial
Dapper Day Hair Tutorial














VERY cute! love all the outfits especially your blue skirt and all the polka dots!
It was a blast. I literally felt like I was in a different decade.
WHAT A GREAT AND WONDERFUL EVENT – LOOKING FORWARD TO THE NEXT ONE !!!
It was a lot of fun. The workers said the first year there were only like 100 people who dressed for it. The second here nearly everyone was dressed for it. It has really caught on.
Pingback: Calling all Disney Fashionistas, It is almost Dapper Day at Disneyland | The In Between Girls