Let's take a look at the first area most people think of when it comes to "what to wear at Disney." Shoes. I hate shoes. It's obvious if you look at how few shoes I own and especially obvious if you look at how few shoes I wear on a regular basis. When I'm in the park I don't wear tennis shoes. Most people do, I know. But, tennis shoes don't match my outfits. Instead, I have found a balance with Crocs. Crocs breathe. Crocs aren't uncomfortable if they get wet. But, let's face it. Some Crocs are ugly. I love the flats and the flip flops. I have my eye on a new sandal though, the Sexi Flip.
Some people have issues with Crocs rubbing but I never have. I make sure that they are slightly sloppy. That's what they suggest that you buy anyway. Back before I had Crocs I'd wear Old Navy's cheap flip-flops. My feet hurt a little but at least I was blister free. NOTHING is worse than feeling like you can't go on because of blisters forming.
As far as the rest of the outfit goes... I like to keep it fashionably casual. I wear a lot of sundresses, rompers, and shorts and tank top outfits. Sundresses are perfect because they keep all my lady parts light and airy. TMI? Sure, but I'm being honest. Rompers are nice because it's one piece and they are normally really lightweight. The only downside is having to pull them down all the way to go to the bathroom which results in you basically being naked while doing your business. As far as shorts and tank tops/t-shirts go I am not a huge fan of wearing denim shorts since they tend to make me really hot. I like lightweight shorts. Not gym shorts. Sort of a khaki material. If I do wear denim shorts then they can't be skin tight or I'll just feel sweaty and chubby the entire day. I just bought a new romper, maxi dress, and a sundress from Forever 21 a month ago in preparation for the trip.
In October the weather is still pretty hot during the day and the nights CAN be a bit chilly so I always come prepared with a sweater/cardigan of some sort to throw on over a dress or tank top. I also always bring a hoodie. Hoodies are lifesavers when it's windy too. Along with my dresses I make sure to have a pair of black leggings with me in case I get a little cold. It saves me from having to change the entire outfit.
Okay, Disney World is not a fashion show and you'll pretty much see everything walking around when you're there. I've seen women in 5 inch heels and guys in overalls. The sky is the limit but you should know that the sky sometimes tends to be disastrous. Still, I'm a gal that likes to look presentable in pictures and even a little cute. If you're a woman and your goal is to look "sexy" at any point during your trip... May I just smack you now? No one, not even Beyonce, looks like a cover girl taking a plunge into the briar patch on Splash Mountain. I have no one to really impress while I'm at Disney World so my level of caring is a lot lower than if I am going out to a nice dinner around town where I'll actually see people that I know.
A very famous quote from The Office sums it up nicely, "Keep It Simple Stupid."