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I love packing for trips, but I'll admit, when I set out to packing for our first trip to Orlando, I was stumped - what are the "must haves" for a trip to the parks? What should I be sure to bring to look nice and feel comfortable for all of that walking?
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*post updated, July, 2019
One of the best parts of any Disney World vacation is that it's so much "more" than just a theme park. With restaurants, shopping, and of course swimming, many days I wear multiple outfits. Naturally, that can make packing all the more difficult. Though you'll certainly spend your days putting 20,000 steps onto your FitBit (which you won't want to forget - it'll make you feel justified in all of the snacking!), you'll likely spend your evening sampling Disney's luxurious dining options and relaxing by the pool or at your hotel.
How do you make sure you've brought all the right clothes for every eventuality? Check out these tips and tricks, and you'll be perfectly dressed, no matter the season! 
The best shoes for Disney World
Beyond a doubt, bringing the right shoes to Disney World should be - by far - the most important item on your list. Shoes are certainly where you should spend the most time and money, as a mistake on the shoe front will come back to haunt you for your entire vacation.
Before we get into the specifics, a couple over-arching tips. First, you must break in your shoes long before your trip. A few wears is just not enough. These need to be shoes that you have worn for full days and been completely comfortable. Preferably, they should be shoes you have worn on another vacation. And second, bring more shoes than you think you'll need so you can rotate. Even the most comfortable shoes will start to hurt after several days in a row. Ok, now down to some specifics:
Dressing in layers for Disney World
Depending on the time of year, don't forget your layers. (Naturally, ignore this section if you're visiting June-August when it'll be hotter than anything).
Something that endlessly surprises visitors is learning that it is not boiling hot in Orlando all year 'round. Our last two visits have been in January/February, and on both visits, we definitely needed light jackets occasionally. On one trip, I actually wore my Barbour coat. The "locals" will always says it's "abnormally chilly," but it's really not - that's just their way of apologizing for the fact you can't go to the pool each and every day. The weather fluctuates - depending on what time you hit the parks, if it's winter, it could be in the 40's/50's and you might want a small jacket...with the knowledge that it may be in the 70's when you return. I'd recommend either a light cardigan that you can easily jam in your purse, or a windbreaker, depending on the time of year. 
Rain gear for Disney World
The unfortunate reality of any trip is that it might rain, even in the happiest place on earth. And you are definitely not going to spend your entire day in the hotel just because of a bit of rain. While you can certainly rock the indelible...Disney poncho, why not just bring an umbrella and some rain-proof shoes (such as the aforementioned topsiders and windbreaker)?
I would highly recommend not wearing pool flip flops to the parks in the rain, as your feet will be covered in whatever sort of germs are on the ground in Disney World, and I think we'd all rather not think about that. Additionally, walking a long distance in wet shoes will definitely cause serious rubbing. Ouch! What to wear for dinner in Disney World
Dinner at Disney is one of the gems of the experience - don't forget to bring clothes for it!!! So many people think only of the parks and forget to pack for the other events on the Disney docket. That said, many of your dinners won't be terribly formal - you'll want more relaxed, Florida attire.
Most restaurants around Disney don't have strict dress codes, particularly the locations in the parks, as many guests just go straight to dinner from a solid day on the rides. But, be sure to check, especially if you're hitting a fancier location, such as the higher end restaurants in the resorts. For me, I don't think you can go wrong with a good Lilly Pulitzer dress, during the warmer months! Classic Florida attire if there ever was some! The best purses for Disney World
Naturally, you are allowed to bring a purse into the parks, as long as they meet the size requirements - I had been curious about this recently, given the restrictions at sports stadiums. But, with so many people having kids in tow, it just wouldn't be reasonable not to.
That said, if you can avoid bringing a purse, I would definitely leave it in the hotel room. Though Disney is purse-friendly, it's always more of a hassle to have one than not. And if you're going to be using Magic Bands, you won't be needing your credit cards/cash anyway! See, Disney has this all figured out! However, for various reasons there are times we all need purses! On the slower rides, such as Peter Pan, Small World, Haunted Mansion, Pooh Bear, etc., you are allowed to bring your purse on with you and just hold onto it. Not sure why, but that always surprises me. As far as actual specifics go, I'd recommend a Longchamp, given it can handle the potential for water OK (as on some rides, such as Pirates, water may invade, just a bit!). Also, you can easily keep it squeezed under your am and you won't be worried about it. If you're feeling more luxurious, perhaps opt for a smaller cross body that can fit more comfortably in your lap/across your body while walking. 
Don't forget the sunscreen and bathing suit, regardless of season
Generally, hitting the pool is going to be on your agenda for a trip to Florida!! Even if it's February and seems like it can't possibly be warm enough, go ahead and bring your swim gear - you'll definitely regret it if you don't, and it's super small, so it'll fit in your suitcase! If you're staying in a higher-end hotel, make sure you know what the dress code is in the lobby (many hotel won't let you run through the lobby in your bathing suit) - thus you may want to bring a more solid cover-up.
No matter the season, and regardless of my previous strictures on rain, don't forget to bring your sunscreen and hat. You'll see many a tourist with a *surprise* sunburn in January - the sun is hotter than you'd expect in Florida, and you'll be outside wandering around lots and lots, even if you aren't sitting out by the pool. I also try to avoid v-cut tops, as they inevitably lead to a weird chest sunburn. 
Picking shorts for Disney World
I'm more of a long pants girl myself, year 'round (yes, even in summer), but there are times when even I must wear shorts. That said, hopping on and off rides, I'd recommend longer shorts, to avoid sitting too directly on any of the rid seats (which, aside from being highly used, also can be hot/cold/wet, etc.) I always bring this pair from J. McLaughlin, which I find to be the perfect length - not too short, but also short enough to keep me cool on those 90+ days for 12 hours out in the parks!
Don't forget the packing cubes
I'd be remiss if I didn't mention my favorite item in the world (found by the Husband, so all props to him!), packing cubes. They keep my suitcase neat and organized and make packing and unpacking easy as can be. Additionally, for the germaphobes among us, you can leave your clothes in the cubes in the hotel drawers/your suitcase, if you prefer. Personally, with as much room as you generally have in a Disney World hotel, I like to spread out, but to each her own!
Thanks so much for stopping by and I hope you have the most magical trip!! Share your packing tips for Disney World below in the comment section! xx
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