My Top 10 Tips for Dapper Day


If you’ve ever paid a visit to my Instagram page, you know that I am kind of obsessed with Dapper Day. I love vintage fashion. I love Disney. Dapper Day merges those two things together in perfect harmony, and ever since the first time Matt and I visited, we’ve been all about it… I may or may not have 10k written so far in a short story about it that’s currently collecting dust on my computer. :X

With Dapper Day fast approaching in this month, I thought I’d share some advice I’ve gathered over the years for anyone who’s planning to join in on the fun.

Hit up your local vintage shops. If your looking for a unique piece, I recommend checking out some the vintage shops in your area. You never know what gems are hiding in the racks of dresses and dresses just waiting to be discovered. Some of my favorites are in the Orlando area are.

  1. Retromended
  2. The Lovely
  3. Dechoes
  4. Orlando Vintage

If it fits and you love it, grab that dress while you can! Nothing haunts you like vintage you’ve left behind. 😥13103397_10154140943469494_7586515446378350384_n

The sunlight is not your friend, and neither is the humidity. It takes a brave soul to wear their hair down in Florida. If you’re taking the risk, pack a scarf or a snood in your purse for the evening, just in case your hair goes flat. Also, prepare for the elements! My emergency kit includes

  1. a rain bonnet
  2. a parasol
  3. sunscreen (here’s my current favorite)
  4. bobby pins
  5. red lipstick (and any other touch up makeup you might need.)
  6. A fan.

Snacks and a water bottle is always a plus, especially if you’re going to be there all day.

Don’t be afraid to say hello! Like someone’s dress? Tell them! Normally, I’m really introverted/shy but this magical day is a happy exception. You can literally greet anyone with a smile and a “Happy Dapper Day” and usually they’ll respond back in kind. I’ve made many a friend by bonding over vintage hats, matching dresses, and sharing hair advice in line for a ride.

Explore off the beaten path. Spot a cute little walkway? An alcove in the mists of the craziness? Guess what friends? It’s photoshoot time! There are some great photo spots hidden in plain sight, or just around the corner. Epcot is especially great for this. (Just make sure you’re not walking past a “cast only” sign.


Make a dinner reservation. This is totally optional! But, If you frequent Disney, it’s nice to have an excuse to go to one of the onsite restaurants. A few years back we went to Primetime which was not only a blast but also has some great vintage vibes. If you’ve had a busy day it’s a great little chunk of time to unwind. The downside? It does make your schedule a little less flexible. But sometimes it’s nice to treat yourself to something fancy while looking fancy.

EDIT: (04/21/2017) Magic Kingdom is going to be offering boxed lunches for a “Picnic in the Park in Tomorrowland from 11-2:30 Definitely a lunch spot worth checking out. More details on

Color coordinate! There’s nothing like scrolling down Mainstreet matching with your honey. ❤

Escape to a quiet spot now and again. Going off of the last point, you’re going to get tired. Take some time to recharge your batteries…both metaphorically, and literally if your phone battery is looking a little low.  We like to grab a coffee and find a quiet corner to people watch, play on our phones, chit chat and just zone out for fifteen minutes. I recommend this to all of my dapper introverts out there.

Wearing heels? Pack a pair of flats. Note: If you ignore this advice, and are at Epcot, hobble over to the World Showcase. The shop in China has some really cute flats that saved my life last Dapper Day. (and I was not the only heel-clad lady buying a new pair of shoes that day.)


What kind of day do you want to have? Do you want to do a bunch of mini photo shoots around the park? Do you want to meet up with lots of friends? Do you want to spend most of the day with your sweetheart? Or meet every single character you possibly can?

We normally just stroll around and do whatever catches our fancy. But it’s always good to talk to your partner, or fellow party members before embarking on your adventure. There’s nothing wrong going to ride Soarin’ or the new Mine ride…however making sure your group is down to wait 90 minutes is a conversation worth having. If you’re in a large group there’s nothing wrong with breaking off and meeting back up later.

Don’t want the day to end? Consider a hotel stay. This can feel pretty decadent if you’re a local. But, if you’re looking for a weekend away and want to enjoy the pre-party and both days in the park it makes sense. Plus, there are often discounted rates In truth, we’ve only done this once for our anniversary. But omg… It was a really nice treat

xo Paige

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