How to Dress at Disney World

Shorts and tshirts.
and you will need to wear socks and tennis shoes. GOOD walking shoes.
It's A LOT of walking. I mean like 10 miles a day walking. You won't realize really how far you are walking.

In May it should be very warm, so you will want to be as comfortable as possible. Shorts and t-shirts. You need to wear tennis shoes and socks. I have been to Disney many times, and there is a lot of walking. The last thing you need is to get blisters from not wearing the right footwear.

Well, I will warn you that at the end of May Orlando is HOT. The sun will be blazing and the ground (asphalt) you walk on will be too. Sandals might look cute and be cooler (temp wise) but the amount of walking you will likely do will make you want something with support. So if you have some sport sandals that are REALLY comfy (no blisters after 8 hours of heavy use in them) then I'd go with that.

I am a Florida girl and have been to Disney many times. If you are comfy in a skirt and tank then by all means wear it. With the age of your L. ones you aren't going on Big Thunder Mountain or the other bigger rides (like you said) so you won't have to worry about it flying all over. If you aren't comfortable in shorts then you aren't going to be comfortable all day and that is miserable. You might consider something like bike shorts underneath just in case so you don't give a flash when climbing in and out of a ride. But you'll probably be ok without.

I am a flip flop girl. I have a pair of Reefs flip flops that I have worn to the parks all day and my legs/back didn't hurt a bit at the end of the day. The Reefs are very comfy. My legs and feet actually hurt more when I wear my tennis shoes. And they are good shoes! Must be my feet rebelling against being closed up lol!

Have a great time!

Comfortable shoes are a must. You will not care what you like if you are in pain because of a poor choice in foot wear. Have a great time:)

First & foremost, wear comfy shoes! (You will thank yourself after each long day spent walking & standing on lines.) Sorry, but a skirt is definitely not ever on my list of Disney park wear! (I've been to Disney World about 25-30 times, I think....I've lost count!) Although you don't plan on riding any 'crazy rides', even getting on & off kiddie rides like Dumbo is much easier done in shorts or capris. I would check the weather just before you are going to leave. It's usually warm in May, but the nights can still get a bit cooler than the days. Always bring sweatshirts/hoodies. Also, the restaurants and indoor attractions can get pretty cold because of cranked-up a/c. Don't worry....I think people have other things on their minds at Disney....Nobody's looking and judging other people's duds....No fashion police there, just people wanting to be comfy & enjoy their vacation. One more bit of advice....Your trip to Disney is not the time to break in a new pair of sneakers or shoes. Stick to the comfy, broken-in ones. Have a great time!

Disneyland or Disneyworld? I go to Disneyland about 2-3 times a month, we live about 45 mins from it. So If you're coming out here, skirts/tank tops and flip flops is perfect. I always bring a light sweater too and if you don't need it you can always rent a locker.

LOL I also hate to have my feet closed up all day in socks and shoes, they get so sweaty, yuk!
Do you have any cute, supportive and comfortable leather sandals? That's what I wear when I'm on my feet all day in the heat, whether it's in an amusement park or exploring the sights of a new city. The key is that they are comfortable and supportive enough to walk around in ALL day, and of course leather is softer and breathes better than vinyl or plastic.
And a skirt? Absolutely! Again, cooler and more comfortable than binding shorts (though if you are able to find some loose, gauzy, linen shorts those are super comfortable and cute too :)
Have fun and don't feel bad about not wanting to look dorky. So many people walk around Disneyland (and many other places) looking awful. I mean, I'm all about comfort, but come ON, this is your vacation! Do you really want to look back at your photos and see a woman in sensible shorts, a baggy top, big shoes and socks and a fanny pack? I think not!

If I were going to Disney I think I would wear some comfortable shoes that can support your feet for hours of standing and walking. Then I might wear a tank and a layered broomstick skirt. I would wear some bike shorts under it to keep my legs from rubbing though. They are made from Lycra and are pretty slick, like a slip but between the thighs....

I think the lighter material of the broomstick skirt would be flowy and allow for air to blow and circulate.

I'd go with Bermudas and t-shirts or tanks.

Skirt and tank top is great. You will be comfortable. I agree. I cannot ever
wear sneakers and socks. My feet scream. This past summer my husband and I took a five week trip across Canada. I had good sneakers.
One week and I went and bought a pair of TEVA sandals. Never took them
off the whole trip. Feet never hurt. We walked all over. Up hills, on dirt
roads, you name it. I absolutely loved those sandals. Used them for
Disney when we went in December. They again proved to be wonderful!
Have fun!

If you are not a fan of shorts, I would do some light-weight capris so you can still feel cool without a skirt - like someone else mentioned, climbing in and out of rides all day will be a pain with a skirt. I would also start shopping around for some sneakers and socks that you can live with - because you will need the support and something that will absorb sweat so you don't end up with some nasty painful blisters. Or some decent sport-type sandals (no flip-flops!) that you can walk around in on a hot day for 8 to 10 hours. There is a TON of walking involved as well as standing in lines and there's nothing like a blister the first day to ruin your trip. I love going around in a breezy summer skirt and sandals in the warm weather too, but I know it would never work at Disney! Sometimes being able to adapt to the environment and survive the experience has to take priority over how you look.

Well, I definately would NOT wear a skirt. You are climbing in and out of rides all day. Wear any pair of comfy shoes...I personally live in Crocs...or any pair of sandals. And any shorts and tee shirt is fine. Don't over think it and have fun!

get the bermuda shorts thats what i wear with a belt and they work great, this way you can ride rides and not have everything showing and still be cool and get good sandles with straps around the ankles atleast

The best investment you can make....is a good pair of support shoes...not flip flops or flat soled shoes...the thicker the sole....the better...as for the clothes...really doesn't matter. I bought clothes that were pink white and black. Some red and blacks...trying to keep up with Minnie and Mickey!!!

How about a skort? If you're going with sandals make sure to get quality ones, preferably with some arch support. It's not uncommon to spend more than an hour in line for rides. Also, bring fold up rain ponchos with you because surprise 5- 15 minute long rain storms pop up out of nowhere.

I live here and recommend dressing comfortable with a good pair of sandals or walking shoes/sneakers. It doesn't get cold at night except in the winter months, but bring a jacket and keep it in the car or hotel room just in case. I see lots of women wearing skirts and dresses to the parks also tank tops etc.

I have also seen plenty of women that think it is a fashion show and they are dressed to the nines with stilettos and all. They are the ones that look so unhappy and hot.

Remember to use sunscreen and drink lots of fluids. I saw a baby this past weekend that was so sunburned. I think the parents under estimated how strong the sun is down here.

I grew up in Florida and as a kid went to Disney every summer, in the last 25 + grown up years I've probably been 20 times. If you don't feel comfortable in shorts, but don't feel like a skirt is appropriate, how about some Capri length leggings or yoga pants and a longer shirt / tunic style? I have a bunch of denim capri pants, and when I am feeling a L. chunky I wear a long sleeve button down shirt out of linen, with the sleeves rolled up, and leave it untucked and hanging a L. long over the rear, sometimes with a fitted tank underneath and then I leave it mostly unbuttoned. The linen and cotton ones that I wear provide great sun protection and aren't really that warm. From experience....lots of it, here is a list of "must brings".
(1) A small bag or backpack filled with rain ponchos and sweatshirts for everyone. You can either stash it in a locker when you get there, or if you are bringing a stroller, stash it underneath way up in the front of the storage basket under the seat....just in case. Summer/spring weather in Central Fl can be rather unpredictable, if you get caught in a mid afternoon shower it is so much easier to have rainwear that you already own, or inexpensive ones from the dept store than to stand in line in one of the Disney stores paying $10 a piece for them! in the evening after being in the hot sun all day, you may feel chilled if you stay for fireworks and parade, or go in any place to eat so the light jackets / sweatshirts will come in handy. (2)Sunblock ...lots of it, and reapply! (3) small snacks like peanut butter crackers etc...keep in another bag at the back of the stroller so you can grab and bring it with you while standing in the long lines.....some times a few crackers are just what kiddos need to keep them happy in line.(4) baby wipes and hand sanitizer...so you can freshen up whenever needed (5) camera...take lots and lots of pictures. As for shoes.......I go either way.....sneakers and socks, or my teva sandals ...stay away from flip flops that may break and leave you stranded and offer virtually no support. I always shake my head in amazement at the women I see there teetering around in high heels and short shorts or dresses...I wonder if they actually knew where they were going when the walked out the door! Also, since it is a family park....I usually find it kind of offensive to be standing in line with someone with itsy bitsy Daisy Dukes on, no bra and a low cut tank with side boob showing or a small triangle bikini top...... I mean really...save it for the Miami beach, but Disney.....standing in line at Small World or to meet Cinderella? Does my husband have to see your boobs? Do I have to endure my 7 year old looking at that?
ETA: If you are staying in the area, or off sight, there are Walmarts and Targets near by that have sections dedicated to Disney themed things...hats, shirts, toys, backpacks etc....at a fraction of the on site prices for alot of stuff. It isn't usually exactly the same stuff.....but similar and some nice things none the less. Have fun!

What ever you are comfortable in is great. Don't overthink it . I actually wore flip flops last year. The first day I wore my "comfortable" sandals and they were not at all . I wore the flip flops the next day and they were great. So, whatever works for you.
My kids love those bottles with the fan an water sprayers. Yes, they are around $17 or $18 but they really help beat the heat. Have a Magical Time =0)