When planning a trip to the most magical place on earth, you will want to pack for comfort and the season. Depending on your style, some outfits may take some planning! You don’t need to wear anything particularly special, but Disney theming your outfits is kind of the culture.

SUPPORTIVE FOOTWEAR

Let’s start with the most essential. You MUST have some comfy walking shoes! DO NOT attempt a day in the Disney parks wearing some basic flip flops. Trust this advice! Your fitness app will know you’re at WDW based on the number of steps you do in a day. Our agents have created a list of our fav women’s walking shoes. Be sure to break them in a little bit before your trip.

PERSONALIZED SHIRTS

A lot of Walt Disney World guests like to have personalized shirts made with their family name or to show that they are celebrating a special occasion. Wearing the same colored shirts helps families and groups keep track of each other in a crowd too. There are lots of fun options available on Etsy.

CASUAL CLOTHES

Comfort is key! Be sure to check the forecast as you start packing. Orlando is very warm in the summer, and just about perfect in the winter with exception to a few weeks that can get pretty cold. I always dress in outfits that are good for lots of movement. Our agents prefer loose fitting dresses (with yoga shorts underneath), or a comfy tee/sweatshirt with leggings or shorts. Personally, I prefer leggings with side pockets for my phone. You can find some of our favorite pieces here, and some fun Disney shirts here!

HATS AND EARS

My kids and I now have a pretty nice accumulation of Mickey and Minnie Ears, and usually end up adding to the collection each trip! If you’d like to avoid the $30+ price tag of the ones sold in Disney gift shops, look for some here ahead of your trip. Hats are another essential for me, because that Florida sun can be brutal. Here is where you can find some fun Disney themed hats.

SWIMWEAR

Don’t forget to pack for the Disney World resort pools and water parks! We’ve compiled a list of fun Disney inspired swim gear!

RAIN GEAR

It is very common for showers to pop up in Orlando, so come prepared. Sometimes the rain can bring a much needed temperature drop, but it can also bring a torrential downpour that chases a lot of guests out of the park. Rainy days can be a really great way to enjoy shorter lines for many of the attractions, so bring the gear and keep enjoying the magic!

PRINCE AND PRINCESS DRESS UP

One way for your little prince or princess to get extra special attention from their favorite Disney character is to dress like them! The Bippity Boppity Boutique is a very popular salon for your babe to get a royal makeover by the Fairy Godmothers. You can purchase costumes at the boutique, or you can bring your own. Here are some great dress-up options!

DISNEYBOUNDING

This is a fun way of dressing like Disney characters using everyday clothes! It adds extra magic to your day, especially if you are attending a special ticket event like Mickey’s Not So Scary Halloween Party. For more information, read our blog post dedicated to DisneyBounding. You can also shop our outfit ideas here. Please read Disney’s guidelines for wearing costumes in the parks here.

STAR WARS: GALACTIC STARCRUISER

Star Wars fans from all over have been loving the Starcruiser experience! If you’re not familiar, the Galactic Starcruiser is a 2 night Star Wars adventure on the Halcyon. This is a FULLY immersive experience with characters that interact with guests and are part of the mission. Dressing the part is not required but encouraged. If you have a Starcruiser reservation, or just really love Star Wars, here are some fun ways to get into character!

Disney vacations require a lot of planning. Let Pineapple Escapes take care of the reservations, so you can focus on packing and getting excited!

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