Ultimate Guide For Dapper Day: 7 Simple Tips For Designing Your Most Outrageous Dapper Day Look

Planning your perfect Disney World vacation takes time and – quite frankly – a lot of effort to nail down each important detail. This goes double if you’re planning to attend one of Disney’s big events. Even the unofficial ones take some additional consideration if you are planning to attend. Disney’s unofficial celebration of vintage style, Dapper Day, happens twice a year in the parks and is host to thousands of parkgoers eager to show off their attire. 

While we’ve written about Dapper Day in the past, we’re going to dive deeper into the event and, specifically, how to dress for success. We’re here to help you create a look for the day that’s practically perfect in every way!

1 – Choosing an Era and a Look 

Before you get started, it’s important to understand what Dapper Day is and what it represents. Dapper Day is a time to explore the fashion of yesteryear in the Disney parks, mirroring the excitement and joy of  Disneyland’s opening day in 1955. While some participants select clothing from that era, popular Dapper Day attire ranges from the 40s to 70s. Although less common, you’ll even see styles from the 20s at times (especially around New Orleans Square in Disneyland). 

While pairing a skater skirt and Peter Pan collared shirt may look adorable, it may not quite match the authentic experience you’re striving to create. You can absolutely wear those things (because this is about having fun most of all!), but if you’d like to go the extra mile, you can focus on replicating a specific look from a specific decade. For example, here are some popular looks you’ll see in the parks: 

• 1920s Flapper 
• 1930s Old Hollywood 
• 1950s Rockabilly 
• 1960s Flower Power 
• 1940s WW II Chic 
• 1950’s Mod 
• 1960s Mad Men Elegant 
• 1940s PinUp 
• 1950s Greasers 
• 1940s Swing 
• 1950s Sock Hops … and so much more! 

By narrowing your look down within the decade, you’ll be better prepared to tackle the rest of the outfit. 

2 – Accessorize Accordingly

Once you have your basic outfit, it’s time to take it a step further. We all know how the little details can make or break your look. While this is true for every outfit, it’s especially important when you’re planning a retro look. Fashion accessories can immediately take any look to the next level.

Hats. You can never go wrong with a great hat. They are versatile, stylish, and a lot of fun to wear (and use as a photograph as a prop – say cheese!). The options for this are endless: pillbox hats, sun hats, fascinators, cloches, fedoras, straw hats, pageboy caps…. We can go on and on! You’re sure to find something that will compliment your look. 

Gloves. If you’re planning to wear a dress or swanky skirt, kid gloves are an absolute must to elevate your outfit to the next level. They add a pop of class to just about everything and help to better date your ensemble. 

Handbags. While you might be lucky enough to snag a garment with pockets, there’s no guarantee you’ll have a place to store your essentials (especially for the ladies). Pairing your attire with a matching (or complementary) period-appropriate pocketbook is practical and gives your outfit an extra wow factor! 

Jewelry. We cannot stress thinking about your accessories enough! When Dapper Day advertises itself as a day of elegance and the debonair, they mean it! With the right jewelry, you take a pantsuit from casual to fab. Large statement broaches were immensely popular in the 20s and 30s, but you can see them dressing up cardigans even today! For the gents, pick a pair of cufflinks and a tie pin that matches your look. Nothing says Disney and Dapper Day like a bit of sparkle!

Don’t forget belts, either! A wide, high-waisted belt dresses up any outfit, as does pairing a  skinny number with a pair of well-fitted slacks. 

3 – Think of Your Feet

This is one where you can sacrifice accuracy for comfort, especially for a long day. Expect long lines and lots of walking (The Magic Kingdom isn’t exactly a small park, after all!), so play accordingly. You’re going to be on your feet for hours. You may want to ditch the heels for the day and plan your outfit around a cute pair of flats. If you must have the height, pack a pair of comfortable shoes, just in case. Ballet flats have always been popular, and many eras prioritize kitten heels over pumps anyway! 

For the fellas, make sure you’ve broken in your loafers or dress shoes before you hit the pavement. Your heels with thank you before it’s over! 

4 – Hairspray!  

Vintage hairstyles can be complicated, especially as many are not often seen outside of special events. That doesn’t mean they are unachievable, however. In fact, they’ll really help you stand out in the crowd if you give them a go! We love seeing Victory Rolls, Finger Curls, Chignons, Beehives, and so many more out in the park! 

We also know they can be a handful to do on your own. Fortunately, there are plenty of fantastic stylists on the web who have created some easy tutorials anyone can tackle on their own! We recommend checking out YouTube channels like A Vintage Vanity, Rachel Maksy, How to be Fancy, and many, many more! 

If you’re considering wearing a wig, think about how long you can wear it comfortably. Then consider how long you’ll be at the theme park. Will it be worth the effort?

5 – What’s the Weather? 

While Florida is known for sunny days, that doesn’t mean you won’t experience some inclement weather on your afternoon stroll. It frequently rains in the afternoon, meaning you might want to plan for the worst on your big, dapper day! Oh, and speaking of sun, you may want to consider some protection in the form of a straw hat (popularized by Disney’s own Dapper Dans) or a pretty parasol to keep you from experiencing the worst those hot days have to offer!

In the spring and fall (typically when Dapper Day festivities are held), it can get a little chilly in the evenings,  especially close to the water features in the parks. If you’re worried about staying cozy after the sun goes down, think about how to pair a cardigan or a suit jacket that keeps you ‘in character’  but provides a little extra warmth. 

6 – Disneybounding? Go Subtle! 

While there is a marked difference between Dapper Day fashion and Disneybounding, the two are frequently combined for the event. Often, the Dapper Day aspects are primary, and bounding is relegated to color blocking or cute accessories to pull the look together. This doesn’t mean you shouldn’t create your own Maleficent-inspired Mad Men era look or a super cute flapper Ariel! Just focus on the spirit of the day, and you’ll be just fine! 

Remember that costumes are not permitted inside Disney Parks! You won’t be able to cosplay, even if your character’s apparel is Dapper, so plan accordingly. You don’t want to be turned away at the gate and forced to make a return trip to the hotel to change. 

7 – Know Where to Shop

Even after you know what kind of look you’d like to create, it can be daunting to find the right kind of clothing on your own. These are some brands we love that have some fantastic options to get you started! 

Cakeworthy. While many of their clothing styles are often more modern than you’re looking for,  they do have some classic pieces that will work in a pinch! However, it’s their other designs that you’ll want for this. They create some fantastic Disney-themed accessories for you to peruse, from hats to handbags. Keep an eye out for a new collection drop every few months. They sell out fast! 

Unique Vintage. If you’re looking for high-quality, gorgeous pieces from just about every era, this is the website for you! Dresses, skirts, pants, tops, and even shoes! It’s everything you need (and in a good variety of sizes!). They also have a “Happiest Collection on Earth” that might have exactly what you needed for your themed Dapper Day outfit. They have all their clothing separated by a decade, making it easier to shop if you know what you’re looking for! 

ModCloth. This amazing website also lets you shop by decade, specializing in the 50s, 60s, and 70s! They have tons of too-cute dresses, cardigans, and accessories! They even have a Hello Kitty fashion line. Meow! ModCloth’s clothes can be considered a tad pricey, but they are quality, and you’ll want to wear them again and again. Most outfits also come in plus sizes!

Beyond Retro. This website caters to menswear as well as women. You’ll find some newer vintage looks (from the 80s and 90s) as well as their earlier apparel. It may take some time to sift through their collections to find what you’re looking for here as it is fairly extensive.

Marketplace Co-Op. This physical shop located in Disney Springs specializes in a lot of higher-end items. If you’re local – or planning a shopping trip before your park visit – you’ll be able to check out their officially licensed apparel at The Dress Shop on Cherry Tree Lane within the building.  They specialize in vintage-inspired dressed themed around Disney’s biggest characters and most popular park attractions.

PinUpGirl Clothing. Another fantastic website filled with perfectly gorgeous options for vintage looks. If you’d like to experiment with bold prints and bright colors, they carry brands like Laura  Byrnes and Deadly Dames to give you clothes for just about every silhouette and size! 

Nello Vintage. This online shop specializes in gently loved vintage apparel. They curate a fantastic collection of items, and each featured piece is styled to give you an idea of how it would look off the rack. 

Dapper Day Shop. It shouldn’t surprise anyone that Dapper Day has branched into apparel and accessories of their own! The organization’s online shop caters to accessories like fans, parasols,  scarves, and enamel pins. 

Tatyana. Another brand specializing in retro clothing, Tatyana even has a dedicated Dapper line of clothes and accessories. If the clothes are a little outside your budget, check out their sales.  They run frequently, and you can snag some fantastic bargains from this brand! 

Etsy. You can find just about everything on Etsy! From handmade Monorail-inspired circle skirts to  Vintage 50s Wiggle Dresses. If you know what to search for, you can probably find it. It’s great for hard-to-find or customized pieces that you can find at just about every price point. 

Local Thrift Stores. Don’t forget to shop locally! You never know what you’ll come across at your neighborhood thrift store. You can always check estate sales for fashionable items or costume jewelry to complete your look. 

At the end of the day, you should be having fun putting together your Dapper Day look (and have even more fun at the park). Don’t worry too much if your entire outfit isn’t officially vintage or if you go for a  simpler hairstyle (after all, how long will those curls last after Space Mountain anyway?). Dapper Day has come to mean many things to many people, and part of the fun is coming up with your own interpretation of an Era,  Look, Character, or favorite part of the park! Let loose, have fun, and don’t forget to share your Dapper Day looks with us in the comments! 

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Cover image graciously provided by Lindsey Thorpe and Ellie. Please visit them on Instagram and show them some love.

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