How to Dress in Disney World in May

Photographed by Michael of Countdown to Magic

May is a great time to go to Disney! The weather is very nice, and crowds are generally pretty good during this month. It can get pretty hot though, so staying cool, or at least trying to, is something to constantly keep in mind. You can spend some days at the parks, and others either lounging by the pool, or maybe perusing shops in Disney Springs.

But before you get too excited, let’s step back and think about everything you might need to bring with you. Here are some great Disney World tips and tricks for traveling to Orlando in May!

How to Dress in Disney World in May

Let’s begin by discussing the weather at Disney World, especially in the month of May.

What’s the Weather?

The average high temperature is around 88 degrees, with the average low at about 70 degrees. So pretty much always hot. While temperatures can get up into the nineties, the humidity is still lower than in the summer months, so at least there’s that.

With this being the general prediction for the month of May most years, I encourage you to plan for the heat, but at least bring one option of clothing if it’s cold, though we will get into more details on clothes later.

With such high temperatures and frequent sun exposure, you should bring a lot of sunscreen or buy when you get there. Also, I recommend wearing a hat and sunglasses throughout the week, to have an extra layer of protection.

Sometimes sunscreen isn’t enough, no matter how good it is. Florida also has a tendency to rain unexpectedly, so you might want to buy some cheap rain ponchos at the store to bring with you, just in case.

For the Trip There

I’m sure most of you have an outfit in your closet that is the one you always wear for travel. It includes the most comfortable pants in your wardrobe, a soft t-shirt or tank top, and a cozy sweater. Or at least that’s what mine looks like. Well, get that out, and start packing your carry-on for a good flight.

If you are driving, then this might not all apply to you, but I also always have a small bag ready with all your favorite items, as I get bored a lot when I’m traveling. In that carry-on are all the things I could possibly need on a trip. It has important things like travel documents, and other stuff like books and games. If you can fall asleep in a car or on a plane, then you might pack a travel pillow that might make your sleep a little more comfortable.

After one trip ended with my luggage arriving at the room six hours late, I always have an extra outfit in my carry-on. It should just be something simple that you can change into when you arrive. If your luggage gets lost, this might be all you have. Also, when you are coming to Disney in warmer months like May, you might want to have your swimsuit ready in this bag, so that you don’t have to wait for your luggage before you hop in the pool and have fun!

What Type of Bag to Bring to the Parks

Okay, this might seem like a simple question, but it all depends on how much you want to carry around with you. Of course, my first recommendation is a nice, sturdy backpack, something that’s not too heavy, but has enough room for everything you need. If you are traveling with the whole family, including a few kids, this might be a bigger list than for others.

If fitting it all in one bag makes it super heavy, try to split it between two, as long as you have someone else to carry the second one. You never want to wear a heavy backpack around Disney World, because at the end of your trip (or just the end of the day), you will have sore muscles all over your shoulders and back, and might even need a trip to the chiropractor.

This might be where you consider another type of bag entirely. Messenger bags can be a good option, but that presents another type of discomfort, with all the weight pushing on one shoulder rather than two. I personally prefer backpacks to messenger bags. People might be concerned about wearing all of their important items on their back, where someone can easily steal them.

But if you have a nice and secure backpack and are wearing it all day, the likelihood that someone will try to steal something is very slim. People in Disney World have other things to worry about. Also, comparing a backpack to other bags, it isn’t any less or more likely to have something stolen from it than something like a regular purse.

If you aren’t traveling with a huge party and don’t need too much, you can go with a much smaller bag. Or if you are lucky, no bag at all, but that can possibly get you into some trouble. A small crossbody bag is a great option here. It makes you limit what you bring, but provides enough space for the essentials: wallet, sunglasses, keys, and similar items.

There are also some medium sized crossbody options, which would be great in cases where it might rain, with room to fit an umbrella or poncho, and maybe a water bottle and some snacks!

Useful Things to Fill Your Backpack

Though this isn’t technically things you wear, my backpack is filled with stuff I use throughout the day. As I wear that backpack on my back, I thought it might be useful to you to know what I generally put in it. First, I pack a reusable water bottle, as it can save you a lot of money on your trip, both during travel and while you are at Disney.

You cannot have a filled water bottle when going through security at the airport, but you can bring an empty one and fill it up once inside. A lot of airports have a bottle refill stations at the drinking fountains, and Walt Disney World does as well.

We all know that at any resort or amusement park water is more expensive than it needs to be. If you and everyone else in your party bring a refillable water bottle then that’s a lot of money saved that you can spend on other things.

A few others things I might have with me are a portable battery to charge my phone or other devices on the go, a portable fan, and an extra bag to carry anything in and out of the park.

If you are bringing snacks like fruit, you can bring them into a reusable shopping back, and one everything is eaten, that is an easy to fold up bag that you can put in a purse or a backpack. At the same time, you can have a bag like that to use when you buy things, saving the shops one more Disney shopping bag.

Clothing for Women

With the higher opportunity for hot weather, this means you should pack a lot of lighter clothing. For women, that might mean shorts and tank tops, or a lot of flowing dresses, though don’t pack stuff you don’t need. If you are going to a nice dinner or show one night, you might want to plan a fancier outfit.

I suggest you only bring one fancy option though, because even if you are going to multiple nice experiences, you can re-wear your outfit. It might not seem right, but it’s very doubtful that you will run into the same people twice on your vacation, and if you do, they understand.

Also, don’t bring any of your expensive or meaningful jewelry, because there’s always a chance you can lose that, no matter how careful you are. If you really want to have accessories, bring a small set of jewelry that you would be okay losing. In the same regard, for your day to day activities, pack a comfortable pair of shoes that you are okay with getting dirty.

Better yet, bring a pair of sneakers that you’ve already worn for years. They should fit well (don’t want to get any painful blisters), and no dirt or scuff will ruin them. You might want to have a nicer pair of shoes for those fancier times I just mentioned. But this can easily be a simple pair of sandals, which don’t take up a lot of space in a suitcase and can be just as comfortable as sneakers.

While May is a warm month in Florida, it might get a little cold in the early morning or at night. I usually have at least one sweatshirt or sweater to wear in these situations. For the same reason, a comfortable pair of pants or leggings would be useful having.

In most cases when I travel, I bring one of my softest pair of leggings that works for my travel outfit, as well as in these sorts of situations. If it gets unpredictably cold throughout the day, having those two extra options is great, and you can always layer a few shirts for extra warmth.

Other essentials that it just doesn’t hurt to say are pajamas, underwear, and socks. You need them everyday of your life, but sometimes you can forget them!

Clothing for Men

For the month of May, men’s clothing is pretty much the same as for women. Have a few t-shirts and tank tops, a couple pairs of shorts, and a nice pair of pants if you are planning a fancy dining experience. Pack worn in sneakers, and possibly a nicer pair of shoes.

For nicer dinners, men just need to be wearing a collared shirt. Sport coats are optional, so you don’t need to wear one, but dressing up nicer is always encouraged.

What is not permitted at Fine/Signature dining restaurants:

Tank tops
Hats (for men)
Cut-off or torn clothing
Swimwear
Any offensive graphics

Along with all that, I suggest you have one warm top and bottom option for if it ever gets cold, and remember those everyday essentials. Also, men should consider wearing hats while they are at the parks, and a watch to keep track of time (though I know you’ll have your phone) might be helpful.

Clothing for Kids

When traveling with kids, you might have to put a little more thought into what they are going to wear. They should have undershirts, short sleeve shirts, long sleeve shirts, a warm jacket, pants, and of course, shoes. I’d also pack a hat to keep their heads warm if the temperature dips.

If you are packing clothes for your children, especially if they are younger than five, you should probably have a few back up outfits in all categories. I know that kids can be messy, especially when they are on vacation and too excited and happy to care.

Some of these things depend on your child’s age. Younger kids will need diapers rather than underwear, and if they are really little, you might dress them in onesies most of the time. I’m sure I missed important things, or that maybe some of these don’t apply to you, but there’s a good start for your Disney World packing list for kids. There are a lot of great sites that have their own more detailed lists, even going in particulars for each age.

Another thing to think about with younger kids, is that they are allowed to wear Disney costumes in the parks, as long as they are less than fourteen years old. This is a great way to encourage your children to get into the spirit and magic of Disney World, and honestly, it might make your packing a little easier.

Maybe that’s all they want to wear the whole vacation, which is fine as long as you can do laundry. Some people purchase costumes for their kids after they arrive, like in the Bibbidi Bobbidi Boutique, while others bring their own from home.

Teenagers can usually pack for themselves, and their selection of clothes should mostly match your own. But if you have older children you are traveling with, encourage them to limit their outfits. I remember myself at that age, and I thought I needed way too many clothes for one week away. It’s safe to say that I wore only half of what I brought. Remind them to only bring what they need, and that they should pack things they can layer.

Just Keep Swimming

When you come to Disney World in any month, there’s a high possibility that it will be warm enough to swim. But May is definitely one of the hotter months, so when you are packing, you should bring everything you might need for a day poolside. There are plenty of Disney pool travel tips out there, but right now we are just going to focus on what you need to bring with you from home in terms of clothing, and a few extra items.

For adults, you should bring one or two swimsuits, unless you don’t like swimming. Sunscreen is really essential, and possibly a hat and sunglasses. People tend to get very burnt when they spend a lot of time out in the sun while in the pool. For women, you might want to bring a cute coverup for pool time, as well as some flip flops or sandals for poolside lounging.

Considering the weather, you might be planning to spend a day or two at Disney World’s great water parks. Walt Disney World has two fantastic water parks: Blizzard Beach and Typhoon Lagoon. The parks will have varying hours, so it’s best to check all of that before you arrive to be sure you can go. For what to bring, many people suggest bringing your own towels. In some cases you may be able to simply borrow the ones at wherever you are staying.

When dressing your little ones for the water parks, there is one thing you cannot bring: floaties. The water parks do not allow you to use any outside floatation devices. But if you have small children, you are allowed to use these at the Disney resorts, so you still might consider bringing them.

I also recommend wearing some form of water shoes, especially for children. Whether it’s flip flops or another style, you just want something to protect your feet as you walk all around on the hot cement, as well as through dirty areas like bathrooms and locker rooms.

If you have any particular questions about anything, such as what you can bring into the water parks, I recommend looking at the Disney Parks Moms Panel, which is a part of the official Disney website. There’s a great search function to find answers about whatever you are wondering about, and it is very up to date.

Events at Disney in May

The biggest event throughout Disney World in the month of May is the Epcot International Flower and Garden Festival, which is the park’s Spring special event, usually going from the beginning of March into June.

The yearly festival first began in 1994, and it features beautiful character topiaries and flowers, along with great food, a staple of any Epcot festival. The park also offers guided tours of different exhibits during this period, and there are plenty of scheduled concerts and activities for both adults and kids.

This probably doesn’t alter any plans of what you want to wear, but it’s always a good thing to remember. Also, the parks sell special merchandise for any event, and maybe you want to buy a t-shirt or something to wear while you are there!

Other events that might be going on throughout the parks will be decided each year, so you just have to keep an eye on the announcements and any online event calendars close to when you are going.

Disney Purchases to Wear While You are There

I always save up some money for my trips to Disney World. With so many great stores and things to by all across the parks and Disney Springs, it’s hard to resist. One staple to any trip to Disney is wearing a pair of Mickey Ears. There are so many different styles to choose from. I know that a lot of guests like to buy a pair early on in their stay, then wear them around the parks. They are also great accessories for photos!

Other merchandise you can wear are the collectible pins! In the stores, you can buy one pin alone, sets of pins, mystery pins, or a starter set of usually four with a lanyard to pin them to. Some people might not be aware of the huge pin trading community that exists in Disney World.

It’s a very simple activity that anyone can participate in. If you have a lanyard full of pins, you can go up to any cast member and ask to trade with them. These pins add some nice flair to your outfits, and trading them becomes a special memory tied to this vacation.

Of course there’s also simply Disney-themed clothing, like t-shirts and sweatshirts. Walt Disney World is constantly updated their line of clothing with new colors and designs, depending on many things, like what special events are going on or current trends of styles.

Also, certain stores throughout the parks might have exclusive merchandise, so keep an eye out while you’re there. I love the feeling of coming back home after a vacation wearing a shirt that I know you can only get in the parks.

Packed and Ready!

With the excitement rising for your upcoming trip to Walt Disney World, there’s no need to stress over packing your bags and what to bring. Hopefully this article helps you out a bit, and you now have an image of what sort of outfits and things you will need day to day during your trip.

Even with this to guide you, I really recommend searching through many of the online Disney packing lists that people have put together, just in case we missed anything important. I hope that you have a wonderful time on your trip to Walt Disney World, and that the weather is great for you. I’m crossing my fingers that you don’t need to use that rain poncho!

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How to Dress in Disney World in May