If you’re visiting Disneyland or Disney World in the Spring or Fall then there’s a good chance you might end up there during Dapper Day! Planning Dapper Day outfits is fun but can seem daunting without a little bit of direction. See how I pulled together vintage inspired outfits for our family for Disneyland’s Fall Dapper Day!
Ok, no this post has nothing to do with home decor. But it does have to do with something else I love – whimsy! 🙂 I never went to Disneyland as a kid, but my husband, Chris, did. He and his family made the trek to Disneyland several times throughout his childhood (his grandparents also lived in California) so I knew that Disneyland vacations would be on the docket for us once we had our own kids. I took my first trip to Disneyland with my in-laws when I was 22. I’m 36 now and have been on 6 Disney vacations since, 3 with kids and 3 without. To be honest, I was skeptical (enneagram 6 here) about Disneyland when I first went. It seemed a little….cheesy? But it didn’t take me long to see why people love it. From the moment you step in the park you feel like you have been transported to a really magical place where just about anything can happen (I basically should work for Disney with a description like that. Am I right?). What can I say? I like imagination! And if you have kids, take your kids to Disneyland (or Disney World, for the purpose of this blog I will say Disneyland but the idea is interchangeable). It’s SO fun!
During planning for one of our trips I was looking at Disneyland outfits and kept seeing all of these adorable outfits. When I showed them to Chris he off the cuff replied, “Oh that’s for Dapper Day”. I had no idea what that was until he explained what Dapper Day was. You can find all of the information and history about Dapper Day on their official website here but in a nutshell Dapper Day is an unofficial event, not sponsored by the parks, that “celebrates fun, refined style from yesterday and today”. There are lots of ways that people choose to dress up for the day. Some people go all out vintage. Some people wear their Sunday best, some will Disney Bound (where you coordinate street clothing to mimic a particular Disney character) and some park goers don’t participate at all! Needless to say from that moment on I knew that my family would have a Dapper Day in their future. That day came last fall when we were able to coordinate the trip to also fall over my youngest son’s birthday.
I really wanted to have fun and have us dress up to join in on the Dapper Day fun, but I was worried about making sure that my kids and husband were comfortable and that the clothing wouldn’t be prohibitive of any of the normal activities we would do at Disneyland. Luckily our outfits proved to check off both boxes! I did a lot of pinteresting, A LOT. There are SO many really cute ideas out there. A lot of them are more aspirational, and definitely more of a one time wear situation. In the end I decided that I wanted a vintage edge to our clothes, but things that looked more ‘real life’ than costume. I tried to choose pieces that had a chance of rewearability (is that a word?) and that coordinated with each other.
For the boys Dapper Day outfits I ordered summer suits that had a jacket and shorts. To keep it comfy for them I paired them with plain white t-shirts that I later added their first initial to in the Disney font with my cricut. To dress up the outfits a bit I added these little hats from Gap Kids. Because I wanted to do Dapper Day but didn’t want cranky kids (that whole path of least resistance thing, you know) I had the boys wear these matching black Toms shoes. They weren’t my 100% favorite choice for the outfit but it was the right choice for all of the walking we did.
(Because you have to have a churro.)
I bought all of the boys stuff last year but these are similar styles that you can find on Amazon:
I knew that in order for Chris to enjoy the day he would have to be involved in the planning. I asked him to look for outfits and he found an inspiration photo that we were able to pull his outfit from. I can’t find the photo now but here is what we came up with:
We were able to source most of his outfit from his closet and the thrift store, with the exception of the hat. I’ve rounded up similar items below in case you’re on the hunt for a men’s Dapper Day outfit like this:
Of course I felt like finding my outfit was the hardest. Very early on I picked up this skirt from a vintage store. I love the skirt but in the end I wish I would have went with a dress because it would have been much easier to finish the outfit. All year I was searching for something I could pair with the skirt! I ended up finding this vintage sweater, which worked fine. A lot of you may roll your eyes that I wore these shoes, but my feet have been dead for years LOL and oddly heels just don’t bother me. I did look for vintage heels but ran out of time. Oh well! In all honesty, if you are a heel wearer it’s not a big deal to wear them at Disneyland. I wore these wedges all day and was 100% fine that day and the following too. Next time (yes family, I plan on doing it again) I will probably wear heels again but will look for a dress, likely still with the a-line silhouette, just because it seems easier.
My sweater and skirt were vintage but here are similar pieces that would work from Amazon:
In the end we all had fun participating in Dapper Day and I loved how all of the Dapper Day outfits came together. Even my boys went with it with minimal complaining. Dapper Day was a fun twist on the usual Disneyland experience and I definitely see us repeating it!
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