I'm leaving for Disney World in exactly 9 days (eek!) and I think I've finally been there enough times to have some handle on what I should pack and what I definitely shouldn't. One of the things I love about Disney trips is that I feel like I can dress even more colorful and whimsical than usual. I know, I know... I don't exactly wear business suits in my daily life, but most of my Disney ensembles push the boundaries of what I'd normally wear at home.
For clothing, I like to opt for simple sleeveless dresses in really fun, colorful prints or comfortable high-waisted shorts with tights underneath. I go a little polka-dot crazy on Disney vacations (blame Minnie Mouse!) and tend to pair most of my brightly colored pieces with pops of black and white. No matter how something looks, though, the key is always comfort. You don't want to be hiking down shorts, pulling up pants or adjusting your neckline when you should be having fun! I usually plan each day's outfit before I go, take mirror selfies at home, and then reference them when I get dressed in the hotel. It makes getting ready in the morning go super fast!
During my last few trips, I opted to wear a backpack instead of a purse. It usually (depending on the size) can hold way more than a purse -- perfect for packing some backup deodorant (trust me, you want to bring it if you're visiting in the summer), some snacks and a sweater or wrap for chilly indoor attractions or cool Orlando nights. And if you're a pin trader like me, it holds way more pins than a pocketbook does ;)
Shoes! I can't stress this enough -- make your shoe choice based on comfort, not style. Style-wise, polka dotted sneakers wouldn't be my first pick for any outfit, basically ever. But I'd much rather spend my vacation enjoying myself rather than limping along in blister-covered feet. Ouch! Unfortunately, I speak from experience. In 2011 I brought along cute shoes that weren't broken in yet and I ended up buying an emergency pair of crocs so that my feet wouldn't be howling at me for the rest of the trip.
My tried and true favorites are the saddle shoes from Payless (#1 below.) They're SO comfortable, I can't even. Plus they look slightly more stylish than crocs ;) In general though, I think any shoes that you KNOW are comfy will work. I've worn my favorite asos t-strap flats with hardly any arch support and my feet were fine. As long as you know the shoes can withstand tons of walking, they should be okay.
In addition to the basics, there are some must-have accessories that I never leave out of my suitcase. If I'm going to be wearing any dresses or skirts, I always pack shorts to wear underneath. Depending on the dress, I'll wear bike shorts or slip shorts (btw, I wear slip shorts basically all the time, even when I'm not in Disney. They prevent wind-triggered flashing and help make unlined dresses look opaque. They're amazing!) This way you can enjoy all the freedom that comes with wearing pants, but you're wearing a dress. Wonderful!
Obviously you also need sunglasses. Extra points if they're pink and heart-shaped ;) But seriously, only bring ones that actually block out the sun. You want to be able to gaze up at Cinderella's Castle without having to squint.
I also always pack some kind of sweater or sweatshirt, even if I'm visiting in the hottest time of year. Some of the restaurants and rides can be really cold, plus after the sun goes down sometimes it can get pretty chilly.
If you have a cell phone, definitely bring a back-up battery. I take a ton of photos and use the Disney World app (it has maps, updated wait times, menus, etc.) so my battery is usually waning by the end of the day.
Last but certainly not least -- Ears!! Of course, you can buy ears at pretty much every store in Disney World, but if you plan ahead you can get some really cute ones from House of Mouse on etsy. They have themed ones for tons of rides and movies, plus these super pretty daisy ones that I have in my own ear collection. I can't wait to wear them with my pink hair next week :D
I also like to pack a lot of the things I'd normally keep in my purse anyway -- hand sanitizer, lip balm, extra bobby pins, etc. If you're going to be staying in a Disney hotel, try to think of every possible toiletry you might need and bring it. They have some necessities in their gift shops but they can be pretty expensive. No matter how hard I try, I always end up having to buy something on every trip -- a toothbrush, safety pins, nail clippers, etc.
And while the rides and attractions are all incredibly fantastic, I highly recommend packing a book or a sketchpad & pencils. On every trip I try to take a little time to sit down and read or draw, and it's always one of the highlights of my vacation. Last September I sat on a bench in a little secluded area with a perfect view of the castle and read for a couple hours while listening to the enchanting music that Disney pipes through the park. It's a really relaxing, peaceful way to enjoy the magic.
And if you do a horrible job of packing anyway, end up with achy feet, freezing limbs and your sunglasses are doing nothing to shield you from the blinding sun, don't fret, Disney has you covered. Your packing folly comes at a price (and usually a steep-ish one) but the stores are well-stocked with everything you might need if you're in a jam ;)