Know Before You Go: Fall Dapper Day 2020

Maybe your usual uniform for visiting Disney parks is a tank top and flip-flops… or maybe you love to look fancy and rock Disney Dress Shop styles. No matter your normal style or comfort level with vintage attire, we’re here to help you get prepared for Dapper Days at Disney!

The Fall 2020 Dapper Day event at WDW will be held November 21-22!

If you’ve never heard of Dapper Day before, that’s fine! We put together a whole post on it a few months ago back when we were ordering outfit pieces. I’d recommend checking that out for background information on these stylish events.

*a note: as the organizers are encouraging people not to travel out-of-state to this year’s event, we’ll be participating in #dapperdayfromhome as well! So stay tuned for another post with details about how to safely celebrate if you’re not a local!

But now that it’s November and Fall 2020’s Dapper Day event is only a few weeks away, we thought we’d share our practical prepping checklist for Dapper Day!

Take a look at the list here and then scroll down for more details about each point.

Dapper Day Prepping Checklist

  1. Do I have the right Park Pass Reservations booked?
  2. Are my outfits right for mid-November weather in Florida?
  3. Am I prepared for the consequences of my shoe choices?
  4. Do I have multiple face masks that match each look?

Do I have the right Park Pass Reservations Booked?

Fall 2020’s Dapper Days will be held inside two theme parks at Walt Disney World Resort, so you must have both a park ticket AND a park pass reservation on the correct days in order to celebrate at the parks.

  • Saturday, November 21 – Disney’s Hollywood Studios
  • Sunday, November 22 – Magic Kingdom

You can check park pass availability on Disney’s website and make reservations through My Disney Experience ASAP if you haven’t already done so!

Are my outfits right for mid-November weather in Florida?

Predictions for Orlando’s mid-November weather based on average temperatures

November is one of the most unpredictable months for weather here in Florida! It’s still hurricane season (believe it or not), so there’s always the chance that it will be hot, wet, and muggy. But sometimes it’s frigid cold!

The secret: layers.

I always design my base layers as if it’s going to be 90 degrees and sunny, even in November. It’s much easier (especially when we’re talking vintage clothing) to add layers than it is to subtract them!

SO… keep your base layers to cotton (or sweat-wicking fabrics, if you can get away with them) and then make sure to also pack:

  • pantyhose (if your outfit features bare legs)
  • a vintage coat, stole, or shrug
  • a hand fan
  • a pocket handkerchief
  • summer and/or winter gloves
A parasol can be a lifesaver on a 95 degree day like this one at the Magic Kingdom!

I’d also recommend preparing for sweat and rain! Many adorable parasols like this one from Unique Vintage come in retro/vintage styles but are actually waterproof – they double as sun-shades and rain-gear!

Are you a Sweaty Betty? One trick to avoid sweat stains on delicate vintage fabrics is to stick sanitary pads inside the armpits of your shirt or dress. They’re not visible from the outside and can be a lifesaver!

Am I prepared for the consequences of my shoe choices?

There’s no doubt that the perfect shoe can make or break your Dapper Day look. Just ask Cinderella’s footmen!

Felt a bit judged for my flats… but he wasn’t willing to trade me for Cinderella’s glass slipper!

But also beyond doubt is the fact that wearing a 1940s kitten heel or wingtip dress shoe all day can be… uncomfortable.

The key here is to make your plans wisely. Are you planning to take pictures first thing in the morning and then go wild? pack a pair of flats to change into! Not interested in changing out of your shoes? Don’t make plans to run around and try to ride all of the roller coasters in one afternoon.

A two-toned Oxford shoe is a perfect finishing touch for any dapper look

And, no matter what, BRING BAND-AIDS! Blisters will happen (fashion is pain) and it’s better to be prepared, or even preemptively slap on a band-aid where you know your shoes rub.

If you forget, each park does have a first aid station where they’re happy to hand out bandaids.

Do I have multiple face masks that match each look?

Face coverings are the ultimate accessory of 2020, and participating in Dapper Day means an opportunity to make or find some stylish new masks.

Every accessory is an opportunity to amp up your dapper look!

I definitely recommend bringing at least two matching masks per day right now, since they tend to get damp from condensation and sweat.

Remember: you can’t take off your mask for pictures in the parks or resorts right now. Cast members were doing a great job of enforcing this rule over Halloween, so make sure that you find a style that complements your look and is cute for posterity.

Well, that’s our checklist for this fall’s Dapper Days! The Fancy Floridian will be at the parks for that weekend, so stay tuned for a lot more Dapper Day content and photos!

And remember: we’ll be sharing all about celebrating Dapper Day from home too, so stay safe!

Be sure to follow us on our FacebookPinterest, or Instagram pages so that you’re always in the loop and can follow along with our adventures!

Pixie dust and glamour!

The Fancy Floridian


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