A Fashion Dilemma: What to Wear in Disney World


I know from talking to countless friends that fashion and Disney are two concepts that usually don’t go together. As we prepare for our upcoming trip, everyone has been stressing to me that the most important thing is to be comfortable (I can hear the collective groan now from Stacy and Clinton from “What Not to Wear.”). Okay, I get it. We’ll be doing a lot of walking in 75-80 degree weather. But it doesn’t mean I can’t be comfortable and relatively cute, right? Why does it have to be one or the other?

Plus, no matter what you say, I will never, ever wear something like this:

But planning for this trip is slightly more complicated because we’re doing more than just going to Disney. We also have a stop at Legoland on our agenda, then we’re spending a few days in Ft. Lauderdale — which  includes an swanky early birthday dinner down in Miami. So I need to pack things that are somewhat versatile and appropriate for the different situations we’ll likely be in.

Here’s what I ended up with:

disney fashion

Disney by Jessica

Basically, a bunch of cute cotton T-shirts and tanks and cotton shorts that can be mixed and matched. I wavered for a bit on getting jean shorts (or “jorts,” as my friend’s husband calls them), but in the end, I couldn’t help but feel like a 14-year-old girl in 1991 whenever I tried some on. So I went for the more grown-up alternative: dark denim shorts from LOFT that are versatile like “jorts” but don’t make me want to do my best Paula Abdul or Janet Jackson impersonation.

I also cannot imagine vacation without my trusty J.Crew denim jacket that I have literally had for 10 years. Love it. And I bought this simple, strapless Old Navy cotton dress last summer that should be easy to pack and I figure I could dress it up with jewelry for our Miami dinner.

Deciding on footwear was easy. I bought the Merrell sandals about three years ago and they rule, plain and simple. (They’ve been discontinued, but good news: this pair is almost identical!). I’ve worn them exploring the island of Hawaii, walking a mile to and from the beach during our Cape Cod vacations and on trips to Storyland in New Hampshire. Basically, they are my go-to whenever I have to do any amount of walking in the summer.

I’ve never once gotten a blister from them or complained after hoofing around in them all day. So that was a no-brainer. I also wanted to throw in a few shoes to wear for other occasions, including some “nicer” flip flops and a pair of black Seychelles sandals (similar to the ones above, or this pair is really cute, too).

But as far as accessories go, I admit I’m having a bit of a hard time. I heart long and chunky necklaces. They’re kind of my thing. But long necklaces + roller coasters = disaster. So I decided to treat myself to small, delicate initial pendant and I’ll pack some cute stud earrings.

Bags, on the other hand, are a little trickier – especially when you have a toddler still in diapers. I am planning to bring our LL Bean backpack with us in the park and pack it full of Mimi’s essentials, and will likely have Dr. G. pack his full of our snacks, sunscreen, etc. But I’m not sure my backpack will cut it on Miami’s South Beach. So I’m also planning to pack my Longchamps Le Pliage bag, which folds up into a totally transportable size and can double as a nicer diaper bag, and a straw Coach wristlet (similar) I bought for our Hawaii trip a few years ago.

Now comes the hard part: Condensing my toiletries for 10 days AND figuring out how I’m going to fit this into one suitcase!

Disney veterans: What’s in your suitcase?


Update: I packed pretty much everything on this list for our trip and I have absolutely no complaints! The sandals were perfect, as usual, and most importantly, I felt comfortable, cute and stylish – but not overdressed or inappropriate – while I was there. Everything was mix and match, too, which was a huge time saver in the mornings.

While most of these items are no longer on sale, I hope this provides a general road map about what to look for: lots of versatile items that combine neutrals and fun colors. And I totally recommend bringing nicer jewelry to dress things up with in the evenings! Hope you have a fantastic time!

Check out my Disney World vacation recaps here, here, and here.


  1. 1

    Iva says

    What great choices!! Just because you’re on vacation with the kids doesn’t mean we can’t look great and comfortable.

  2. 3

    Lollie ~ The Frtuitous Housewife says

    Looks like you’ve got a great plan for balancing Disney-comfort & style. Good for you!

    We’re heading down to W. Palm the beginning of May, with a trip over to the Bahamas w/ friends & all I’ve managed to do is mail in the passport applications for the boys and get them new Crocs. Will you come help me plan a W. Palm, cruise over to the Bahamas, comfy & Mommy-friendly wardrobe?

    Have a blast w/ Mickey & Minnie.