Dapper Day…it’s one of my favorite things all year! Since learning about this lovely event series last summer, I’ve attended twice and it’s sparked some major paradigm shifts in my life–all for the better. This spring, I’ll be attending the full weekend at WDW; a stretch for me since I’ve only ever done a single day at the parks. I’ll be blogging about that experience soon, but in the meantime I wanted to share what Dapper Day means to me, how it’s benefitted my life, and tips I’ve learned to get the most out of the experience.*
I’ve studied and admired vintage/retro fashion for most of my life, but didn’t fully embrace the style as part of my daily life until rather recently. Though I loved all the lovely fashion from the 20s/30s/40s/50s, I tried for the longest time to discover a style sense that fit in with the trends but still felt like me (heaven knows, that’s pretty darn impossible!). Looking back, I see that retro clothing/hair/makeup/accessories has always held my heart. Roughly three years ago, I finally embraced my true, authentic (and retro!) self full time. Though it took time to build up to where I am now, I began to feel much more comfortable in my skin the more I embraced it.
The first time I heard about Dapper Day was on Instagram. I saw women my own age dressed up in the styles I adored, but it felt more real than the pinups I followed. Something about seeing people dressed in crinolines, bow ties, swing dresses, and carrying parasols in the Disney parks hit me in the gut. I thought, “Wait…I can be a part of this?! I can be around other people that love this as much as I do?”
Fast forward, and I am now an annual WDW passholder. I’ve spent an embarrassingly high amount of money to bling out a Mickey hat. I have also cut my hair into a true vintage middy style. Sure, these things sound trivial, but for me, these are meaningful outcomes of what Dapper Day did for me: In short, I have become more authentically myself because of these outings. Dapper Day is now just my daily style turned up to 11. Dapper Day is the chance to play with parts of my personality, create for the sake of creating, and have fun…because fun is essential to wellbeing.
There’s so much I enjoy about Dapper Day, and I hope you can glean something useful. Not all of these suggestions will work for everyone, and that’s okay! The one take away I can offer you is this: if you haven’t been before, I strongly recommend trying it out!
- Half the Magic is Who You’re With. Great friends made my first Dapper Day more magical than I could have ever dreamt. My first Dapper Day was with a great combo of friends that had the same mission: enjoy the day! And here’s what truly interesting: I also felt like I found my tribe there. When you “do” Dapper Day, the park staff say things like “Happy Dapper Day”, and “Looking dapper, ladies!”. Other Dapper Day participants compliment your style, and everyone is so much more friendly than a normal day at the park. It’s the most unironic, kind, and genuine reactions you can get while dressed head-to-toe in retro style.
- Dapper Day is What You Make It. For me and my lovely friends we have found (both for Dapper Day and a regular day at the parks) that not having an itinerary helps a lot. Sure, having annual passes and living within reasonable driving distance makes a HUGE difference in being able to just “go with the flow” of the day. But we have also found that the best parts of the experience have come during the times when we weren’t trying to make something happen. If you try to pack too much into your day, or force things to happen, you’re probably not going to have the best experience. Our group got fast passes both outings, but for everything in-between, we allowed ourselves to go with the flow. And guess what?! The moments of serendipity were our favorite parts!
- Wear. Comfy. Shoes. I honestly can’t stress this enough. It never ceases to amaze me the number of (mostly) girls that wear heels that look great but aren’t great for walking. I can totally understand wanting to look good for photos (that’s a big part of the day!), but don’t make yourself and everyone you’re with miserable because you get a blister an hour in to an 8 hour day. These events are at a theme park, and you’re going to walk miles. I recommend selecting shoes that go with your outfit color-wise, but are comfy enough to take you all over without compliant. Besides, we seldom see your shoes in the photos anyway!
- Mind the Weather. Okay, so this might just be a Florida thing, but Dapper Day is in late April and late November–two times of the year that are typically humid and hot. Seriously, we have two seasons: Summer, and “Was that a breeze?”. If you’re going to WDW for Dapper Day, be thoughtful about your attire and the material it’s made out of. And for the love of all things holy, WEAR SUNSCREEN! A parasol can be really helpful for keeping the sun off your face/shoulders, and is tres chic! I will also recommend you eat lunch a little early to beat the rush, and then find an indoor show to watch to help avoid the heat of the day. Heat-related illness is no joke. Especially if you are wearing crinolines.
- Sign Up for the Emails. I got the coolest photo with one of my pinup idols, Doris Mayday, all because I signed up for the official Dapper Day emails (and read them!). Seriously, good stuff in those.
- Wear What Feels Right. Some people wear clothes they bought online. Some people wear clothes inspired by Disney characters (or rides!). Some wear outfits they made themselves. All these things are acceptable. “Dapper” means whatever you want it to mean. Fall 2017, I wore a dress that was made out of a fabric that looked like my Mammaw’s kitchen curtains, and a small fascinator that looked like a cherry pie. My first Dapper Day, I accidentally twinned with someone, and it was awesome. My advice for picking what to wear is by asking yourself some important questions: 1) What makes me feel really good to wear? 2) What can I wear that will be comfortable to wear all day, on rides, and in the heat? 3) Is there anyone or anything I want to evoke?
- Focus On What Is Most Important. This kinda goes back to #2. If what you value most is photos of your group, let your group know that. If what you value is getting that amazing La Vie En Rose frozen cocktail in France, make sure you declare it before you leave the house. When everyone in the group knows what each other wants to do, it’s easier to be patient and be present throughout the day. My team already knows that my top priorities this Spring outing is a photo with a Dole whip outside the Enchanted Tiki Room, and to go to Trader Sam’s Grotto. I know that one person needs a photo in front of the monorail. Because we’ve outlined what’s important to each of us, our time together is going to be fun–instead of frustrating.
I would say that most of these tips are applicable to any trip to any theme park. Dapper Day is a particularly special occasion, and my hope is that anyone attending walks away with a full heart. Have Dapper Day recommendations? Let me know!
*This post is NOT sponsored, and all the above opinions are my own.
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