Guest Post: Dressing for Dapper Day at the Disneyland Resort

It's my pleasure to welcome my *first* Guest Blogger here at Dressing For Disney. Kelsey and I met through Instagram and our mutual love of Disney history. She's being modest when she says *I* invited her to write a guest post, as it was *her* genius idea in the first place. I'm so glad she approached me about it. I really enjoy this girl- and may even crash on her couch for some of the D23 Expo in August (surprise, Kels! ;) Enjoy her look at Dapper Day in Disneyland!

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Hi ya'll, my name is Kelsey and I'm a Disneyland Annual Passholder. I'm excited that Ashley invited me to write a guest post on dressing for Dapper Day at the parks!

For the last three years, I’ve had the pleasure of going to Disneyland Resort’s Spring Dapper Day. I don’t even remember how I heard about it, but the minute I did, I was hooked. For those of you unfamiliar with Dapper Day, it was created to honor the spirit of stepping out in style to the Disney parks. Inspired by concept artwork for Disneyland in the 1950’s and 60’s, it harkens back to the day where everyone dressed, well, a bit more dapper. There are currently Dapper Day events at Disneyland Resort, Disney World Resort, and Disneyland Paris. For more info, check out the Dapper Day website.

There is no rule about a particular time period to dress to, and people show up in everything from flapper dresses to circle skirts, to more contemporary dress. Many people even Disneybound (dress in an outfit that is inspired by a specific character). As someone who loves the history behind Disneyland and the time period in which it flourished, I tend to choose more 50’s or 60’s styles for Dapper Day, although that is not always the case. My Dapper Day outfits have run the gambit from vintage, to vintage inspired, to contemporary. I’ve mixed and matched pieces that I already had with new finds, and reused tried and true accessories.

Spring 2013, my first Dapper Day. I went shopping last minute and picked up this dress and belt at H&M. The pearls were some I had, and the little gold owl pin with my great-grandmother’s (GG’s). I also had my GG’s vintage handbag and a pair of black gloves.

Spring 2014. This dress was the most amazing find at an antique store back home. It’s vintage, from the 1960’s, and came with a knee length jacket from the same fabric, with a single button at the top (Very Jackie O!). (Editors note: THIS DRESS IS FREAKING AMAZING!) It was entirely too hot that day to wear the jacket, so it is sadly sitting unused in my closet. Paired with the dress are costume jewelry pearls (my GG’s), her owl brooch again, and white flats from Payless. I also had a white leather clutch.

Fall 2014, the only fall Dapper Day Soiree that I’ve been to. Pink and black vintage-style dress from Nordstrom, same pearls and owl brooch with elbow length vintage gloves (again, GG’s. They still had the price tag on them from well over 40 years ago!). I got lucky and found the fascinator days before in a funky shop at the mall.  Paired with pointy patent flats (which gave me blisters, so ladies, take note to wear comfortable shoes that you can easily walk in!) and the same black handbag of GG’s.

I was torn on what to wear for Dapper Day this year. I had bought a circle skirt for an Oswald disneybound, but had been frantically trying to find a period-appropriate blouse to pair with it for warm weather (because Dapper Day was ALWAYS in the upper 70’s-mid 80’s). Then something amazing occurred 5 days before the event. Weather.gov stopped predicting 76 degrees and suddenly it was going to be in the mid 60’s!!! Sweater weather and I had the perfect black sweater for my ‘bound. For a few moments, I contemplated re-wearing my yellow dress with the jacket this time, but that got nixed when the forecast called for rain (seriously, in Southern California we get rain like 5 days a year and this had to be one of them?!?). Suddenly my mind went from “Oh yay, cool weather!” to “Oh crap, my hair is never going to hold a curl in that weather so how do I rainproof my outfit?” Luckily, the answer wasn’t too complicated. I managed to find a wooden handled umbrella, big enough to totally cover me. For my hair, I curled it, then brushed the curls together and pinned them down before hair-spraying the crap out of my head. Coincidentally, my new pea coat that I bought for our honeymoon was perfect with my outfit, so if it got really cold, I had a backup.

I was really happy with how my outfit for this Dapper Day turned out. I didn’t need my coat until the evening, and while it poured for a few hours in the morning, by 2:00pm it stopped and the rest of the day was cloudy but dry, perfect for photographs without pesky shadows. I didn’t start the day in my Oswald ears, but decided after awhile that I wanted people to actually be able to recognize my disneybound, so I put them on and left them the rest of the day. I got a lot of compliments on my ‘bound, and had a few people even want to take pictures with me! I spent most of my day with two friends, but had a few hours by myself to just wander around and people watch, one of my favorite Disneyland activities!

Of course I had to take a picture outside of "Oswalds"!

I was worried that I wasn't going to get to see Oswald because he wasn't going to come out if it was raining. Luckily, the rain let up and I got to see him!

I’ll leave you with a few tips for having a great Dapper Day:

• Pick something that you’re comfortable in! If that means a modern dress or slacks instead of a circle skirts, go with it! The last thing you want is to be uncomfortable and self-conscious the whole day.
  
  
• The above includes shoes. Ladies, if you’re not accustomed to wearing heels, I probably wouldn’t break them out for Dapper Day. Additionally, make sure whatever shoes you’re wearing are ones that you’ve broken in before. Blisters at Disney are no joke!
  
  
• Accessories make the outfit! Brooches are back in style and fairly easy to find in vintage stores or on Etsy. My Disneyland “D” on my black sweater is from Match Accessories on Etsy. They makes tons of fun Lucite accessories and they are sooo nice and accommodating!
  
  
• Be confident! You’re stylish, you’re participating, and you’re a part of an awesome group of people! There’s lots of camaraderie between dapper dressed people! You may get questions from non-participating people about why you’re so dressed up, but just explain and own it!
  
  
• Take lots of pictures! I always regret not having more.
  
  
• Talk to people! Compliment people when you like their outfit, it’ll make their day!

A big thanks to Ashley for letting me share my thoughts on Dapper Day! If you have any questions for me, you can find me on instagram @Knoxie13 or on tumblr here.