How to Pick and Plan the Perfect Dapper Day Outfit for Disney

It’s the best unofficial event at Disney parks. You dress up and get to see tons of other guests in their Sunday best.

If you’ve never visited Disney for a Dapper Day Outing you will absolutely want to read about the 7 Things You Need to Know Before Visiting Disney for Dapper Day. It’s a quick hitlist about crowd levels, expectations, and the entire experience.

Dapper Day is all about showing off your classiest style. The parks are suddenly filled to the brim with zoot-suites, pastel dresses, and more hats than opening day at the Kentucky Derby.

You’re gonna love it.

There’s a lot that goes into picking and planning an outfit for the occasion. My first choice would be a giant hoop skirt with bustle ala Scarlett O’Hara, because I’m still looking for an excuse to wear that, but I don’t think it would fit into the Space Mountain ride vehicles (or any others, really).

That’s why we’ve compiled our top 7 tips for How to Pick and Plan the Perfect Dapper Day Outfit!

Portray your favorite character(s) with color blocking and pattern matching

Or Disneybound, as the kids are calling it these days.

The concept is simple, create an outfit that mimics, mirrors, or is inspired by a Disney character. You can achieve this in a number of different ways, but color blocking and pattern matching are my favorites.

Color blocking just means that your outfit is made of the same colors a character wears. If you’re bounding as Ariel, for example, you’d wear green and purple since her tail is green and top is purple.

Pattern matching is a similar concept to color blocking but it goes a step further. The best example of this is Minnie Mouse, of course. Her white polka dots are iconic!! Don on just about any piece of red clothing with white polka dots and you’re golden.

Pinterest is a great source for outfit inspiration.

Consider a hat or parasol

First, because they’re fancy AF and that’s sort of the point. But these items serve a functional purpose as well.

It’s funny actually that for many of us a sun hat or parasol is a style item, usually for a beach vacation amirite. I can honestly admit that wearing a wide-brimmed hat for the purpose of blocking the sun or anything else has literally never crossed my mind.

And that’s the functional purpose, of course, to protect your eyes, head, and face from sun exposure. Both Florida and California are known as particularly sunny states, one is even known as the Sunshine State!

Spending all day in the heat is difficult enough on a regular day but ad crowds and dapper apparel, and that is a recipe for sweat, sunburns, and a lot of irritation.

So, when you are planning out your perfect Dapper Day outfit think about how you can incorporate one of these fantastic accessories to add a little extra flair (and protection).

High heels are a go-to, but consider flats – or at least sticking some in your purse

I was jaw-dropped speechless the first time that I attended the Dapper Day Outing. So many girls were wearing high-heels and all I could think about was their poor aching feet.

Spending a day at Disney, any day, is a lot of walking. There’s really no way to avoid it, you can minimize it, but you do have to navigate back and forth a lot.

Tennis shoes or gym shoes are always going to be your best choice. They’re comfortable and made for use. Problem is, they’re definitely going to clash with the gorgeous look you’re planning.

Check out our guide to the Best Shoes for Disney

The next best thing would be flats, ballet flats like Tieks are marvelous. They’re comfortable, stylish, and easy to pack in your park bag. Rocking these all day would be a breeze, but alas I too am called to the allure of those sultry 6-inch stilettos.

Fun fact about me; I own more shoes than silverware! Have I worn them all, lol nope. But they make excellent decorations for my closet and Marie Kondo isn’t coming anywhere near them!

If you absolutely must strap on the sky highs – go for it. BUT don’t be a hero. You don’t need to wear them all day. Limit your walking by using the Disney Railroad and taking frequent breaks.

Nobody wants to come home from a day at Disney with blisters and corns!

Make sure you can move!

The other shocker is the number of girls who attend Dapper Day in corsets. 😨

I love them, they’re fabulous and I’ll tie myself into one now and again when the Rocky Horror Picture Show comes to town. But I am 100% not going to Disney in one.

And I don’t think that you should either.

Yes, Dapper Day is the perfect occasion to go all out. Frills and lace and high heels and bow ties – perfect. But let’s not forget that it’s still a theme park. There are still lines, and rides, and shows, and parades. And if you can’t bend over or sit down it’s not going to be any fun. 

I honestly even question some of the suit jackets I’ve seen men wearing to the event, as they don’t look easy to move in to me. But they’re the absolute essence of dapper, I can’t imagine the day without them.

Save room for snacks

There’s so much good food at Disney it’s almost become an attraction of it’s own. From Lobster Nachos at Pixar Lounge to Hand Rolled Sushi in Epcot – it’s everywhere.

How can you possibly go to Disney and not get a Dole Whip, or a Mickey Premium Bar (which are sold in stores now BTW). It’s basically a crime. It’s all still fast food though, well mostly, and contains a ton of salt, carbs, and deliciousness (or fat if you insist we go by the Webster definition).

I’m sure you know what happens when you load up on all that deliciousness, ya? You get bloated, you feel lethargic, and things get tighter. There’s a reason everyone wears sweatpants to Thanksgiving – oh is that just my family? 🤷‍♀️

Do yourself a HUGE favor and leave some room for snacks. Don’t buy the pants if they’re just a 1/2 size too small or the dress that only zips when someone holds the top together. After a few hours of indulging you’ll be so uncomfortable or worse (and it’s happened to me) something will rip.

There’s no shaming here, snack it up to your hearts content! Just plan ahead for the…after effects.

Check the weather

Is it going to rain? Will it be 110 degrees? What if the wind is so strong it picks up your skirt in the middle of your castle backdrop photo on Main street?

All of these can happen, seriously. And they can dictate what you wear. If it’s going to rain you absolutely need to accessorize with a parasol or umbrella. When the humidity is off the charts, as it often is in Florida, you’re going to want to put your hair up.

The second you decide to go to Disney for a Dapper Day Outing, check the weather. Check it again when you have an idea for your outfit.

And again when you go to shop for your outfit. Check the weather often, forecasts can change fast.

Do a test run

This one’s a fun one.

Now that you’ve heard all the “be prepared” points there’s just one last thing to do. Make sure your perfectly planned Dapper Day outfit is just that.

Try it on! At least for a few hours if not a full day. The whole thing.

Do your hair, do your make-up, see how long your feet put up with those shoes. It’s much better to find out ahead of time something doesn’t work than get flustered and frustrated in the middle of a hot crowded theme park.

Plus, it’s a good excuse to dress up anyway. Ask your significant other out to dinner somewhere fancy and make full use of it.

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