Disneybound Breakdown: Dapper Dan

Hello Disney lovers,

I can’t help but write this post with a song stuck in my head. For the past few days, I’ve been hearing the words to “Mr. Sandman” over and over. Well, I already have the prince of my dreams, but I can’t help but think that Mr. Sandman also brought me a dream outfit for a day at Magic Kingdom: a Dapper Dan Disneybound!

In case you’re not familiar with the Dapper Dans, they’re the classic barbershop quartet that pop up a few times a day on Main Street to serenade Disney goers young and old. In addition to some killer harmonies, the Dans have iconic Disney style. So as I hum along to their songs, I’ll share how I put together my Dapper Dan-inspired outfit.


dapper dans 3
A ladylike Dapper Dan. Does that make me a Dapper Danielle?


The dress: This was the shining star of my Dapper Dan ensemble. The Dans’ most eye-catching fashion statement is their bright, colorful stripes, so I had to find a dress that fit the bill. Now, each member of the Dans rocks his own color of the rainbow, but because red is my favorite color, that’s what I chose. You can pick any color really, as long as the outfit has alternating colored and white vertical stripes. I found this dress on Amazon, and it was practically a steal at $23. In addition to the bold pattern I needed, it also has a full skirt that makes it feel delightfully vintage. If dresses aren’t your thing, you could find a button-down shirt with vertical stripes, and a coordinating skirt or pants (pick the same color for the bottom as the color of your stripes) and you’ll be singing your own Dapper Dan tune!

The hat: The Dapper Dans’ accessory of choice? A classic straw boater hat, of course. If anyone is going to bring these hats back to the mainstream, it’s the Dans. I got this precious mini boater hat from Hat and Mouse, a small shop I discovered on Etsy a year and a half ago. This lady-like version features a red ribbon and matching striped bow, a perfect complement to my dress. And not only is it adorable, but it’s comfortable and secure thanks to two alligator clips that keep it in place all day. Unfortunately, this hat is now a retired design from Hat and Mouse, but you could easily make some DIY magic with a regular boater hat (which you can find online) and colorful ribbon. And for your other Disney style needs, I still recommend checking out Hat and Mouse for more whimsical fascinators and ears!


dapper dans 4
With a song in my heart and Starbucks in my hand, I can do anything!



The shoes: The Dans traipse around Main Street in tap shoes and spats, but that’s not exactly practical for a regular park goer. I pulled off a similar look with a simple pair of black and white saddle shoes, bought from Amazon. They cost about $25, and were surprisingly comfy for an inexpensive pair of shoes. A word of warning though, they’ll give you the urge to do a quick shuffle step when the Dans start singing!


dapper dans 6
Saddle shoes: Perfect for twirling!


The bag: I wanted my purse to serve as another nod to the happy music of Disney, so what better to “carry a tune” in than a piano key wristlet! I found this one at Charming Charlie in my local mall for about $20 (I originally bought it for a Marie Disneybound). It’s big enough to hold all my essentials, plus a very small umbrella, which is a must on a summer day in Florida.


dapper dans 7
Dapper Dans: Can you carry a note? Me: I can carry plenty in my bag!


The belt: The dress came with a thin red belt, but I decided to replace it with a wide red belt I already had at home. The purpose of that was two-fold…First, the wide belt gave the dress a more cinched waistline, and second, the knot in the front was a subtle nod to the Dapper Dans’ bow ties. That way I was able to invoke that dapper feel, without the need for me to wear a real bow tie.


dapper dans 2
Ready for a job on Main Street!


Other accessories: I chose to keep the rest of my accessories relatively simple for this outfit, so as not to compete with the bold stripes of the dress. I grabbed some retro-looking gold sunnies from Charming Charlie, and some simple clear jewel earrings. I also wore a red Disneyland “D” brooch that I bought on Etsy, just to add another touch of sparkle.

As with many of my Disneybounds, this outfit really enhanced my experience in the park. As I was taking pictures in front of the barbershop first thing in the morning, the Dans saw me before they even made their grand entrance to the park for the day, and they walked out just to say hi and appreciate my outfit. Talk about a unique photo op! They loved my hat and told me I looked like I belonged on Main Street. Of course later in the day I had to stop by and watch them perform, and they made sure to sing a song directly to me in front of the crowd!


dapper dans
Day 1: They’ve already accepted me as one of their own…


So there you have it…the steps to creating an outfit that would make even the most Dapper of the Dans swoon. This ‘Bound is sure to help you hit a high note with your Disney style, and make you a mainstay on Main Street!

See you at the barbershop,

Jiminy Jenny


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