“Are you gonna do those matching shirts?” Hands down this is the most common question I was asked anytime I got into a conversation about planning our family trip to Walt Disney World. Part of me wanted to embrace the stereotype and be that family. The other part, knew my family wouldn’t be into it, but I still debated doing it ironically. Clearly there was something to this that I needed to explore.

One of my absolute favorite things about any trip is figuring out what I’m going to wear. It’s the one moment I actually put effort into fashion, even though I’m the last person to ask about fashion. The trouble is, I didn’t actually own any Disney clothes and I hadn’t really thought about what might not be horribly uncomfortable trudging around the parks in the August heat.

I decided to start small and focus on Miss O. Since we were surprising her with the trip on the morning of our departure, I needed to get her bag packed without her input. It’s usually easier that way anyway, but she’s got so many opinions lately, I knew I would be taking a risk even considering choosing clothes for her. Fortunately, I pay attention and I know what she likes.

She already has a couple of favorites, like the Pirates of the Caribbean shirt I got for $3 in the clearance section at the Disney Store. She had just professed her love for Captain jack Sparrow and I figured for $3 I can get on board with that. She wears it once a week and I honestly panicked that she might outgrow it or tire of it before the trip. Fortunately, it’s still in the weekly rotation. Unfortunately, that means I probably have to wash it the night before we leave.

I took stock of her wardrobe and matched shirts she already owned with the parks we would visit and any character meet and greets I knew we had in our park plan. I bought a couple of new shirts for her, too, because why not?! Miss O was obsessed with Lion Guard and adores cheetahs, so I found an embroidered Fuli shirt from LittleGiggleShop on Etsy for our Animal Kingdom day.  I couldn’t ignore a sparkly R2D2 t-shirt from the Disney store summer sale for our day at Hollywood Studios. I ordered it months before I ended up making a storm trooper shirt for her Star Wars birthday. Oh, well. That’ll go in the bag, too. It’s good to have options.

I’m a member of lurker in a couple of social media groups for fans of DisneyBounding, where you use your personal style to emulate Disney characters, but I wasn’t ready for that level of fandom. They are pretty great for inspiration, though, and I ravaged my closet to see what I already owned that I could turn into a subtle nod, known as a baby/casual/closet-bound, and have a little fun of my own. It turns out my wardrobe is pretty boring and after curating Miss O’s trip wardrobe, I had to admit I was starting to feel the lure of those shirts.

I already had the framework from what I pulled together for Miss O, so that became the starting point for building my own outfits. I also embraced the mom in me and invested in some golf skorts for the park. Let’s face it, the weather is going to be hot, humid and flat out gross. My usual skinny denim Bermuda shorts were going to feel like plastic sausage casing around my legs and leave no room for the Mickey Bars we all know I’m going to eat. My new mom skorts are lightweight, moisture wicking, and hella comfy. Bonus: they’re actually pretty cute and I’ve been road testing them all summer. All I needed to do was find some shirts that I could pair with pink, green and grey, then add in my extensive selection of Converse all-stars (yes, I have insoles in them), et voila!

About a month before our scheduled departure, I get a text from my sister-in-law, Auntie L, asking about getting group shirts for the first day. Turns out the magic got to her, too. It’s these moments when being a planner can seriously bite you. I’d had Miss O’s and my wardrobe plan set for at least three months by then. I hadn’t fully considered our first day though, which was technically a travel day. I had a Minnie Mouse shirt I bought at Target for Miss O as part of our trip reveal plan, but I hadn’t thought to do anything fun for me.

I mentioned it to Hubs, who’s one concession to joining me in “fun shirts” was a shirt I found with one of his favorite things about Disney World, the monorail announcement. He fiddled around on Google for a bit one night, flashed me a picture, then asked me if I could make him a Star Wars inspired shirt like Miss O’s. Um, hells yes, I can make you a shirt! I have this amazing Cricut Maker sitting downstairs just waiting for another project.

Now that he’d given in, I had to find a shirt for me. I could not plan every inch of this trip and be the only one on that plane without a themed shirt. I figured I’d find a classic Mickey ringer t-shirt, like I had when I was a kid. Easy-peasy, right?

Not so. While I found lots of versions of the shirt I wanted, every shirt I found was either junior-sized, which I am definitely not, not what I really wanted, or not long enough. I’m pretty tall, so finding a shirt that’s long enough to not make me look like bad-day-Brittany can be pretty challenging. I usually shop the tall section of Old Navy and Gap.

Honestly, sometimes I cannot see the forest through the trees. I got a tall-sized t-shirt off Old Navy for $5 during their end of summer/back-to-school/when-are-we-not-having-a-sale sale and finally put my Cricut to work for me for once.

This trip is starting to turn away from stressful logistics and get really real. It helps to embrace the magic and let yourself have some fun, which we really need since our beloved kitty passed away two weeks before our trip. Full-on matching family shirts or not, I know we’re going to have a great time, no matter what we’re wearing.