We skipped our annual holiday family trip to Walt Disney World in 2020, so it was an absolute dream to be back this year. Better yet: even more family came than usual. At one point, we had a party of 15! After being away from my family for an entire year, togetherness has been more important than ever. We had such an amazing time!

3 Holiday Disney Outfits

That being said, we were hit with a cold front as soon as we went on our trip and the weather couldn’t have been nicer. It was in the 60s, so did I need a tiny Mickey scarf? Obviously not. But it was part of the outfit. Leave me be!

Outfit details: Thrifted (and shortened) jumper dress, vintage Mickey scarf, Bobby’s Mickey Santa hat. My grandma bought me this shirt — she has the same one! She got it at Kohls.

We stayed at the Art of Animation hotel, which is our favorite place to stay when we are in a large group. It’s perfect for families with multiple kids. And honestly, even as adults, we LOVE it. We stayed in the Nemo rooms, but the Cars area’s theming is my favorite!

Outfit Details: Matching Mickey and Minnie sweaters from Shop Disney, handmade Minnie Mouse ears (check out my DIY Minnie Mouse wreath ears tutorial), vintage shorts, tights, old flats.

I bought this dress from the Shopbop sale right before our trip and it was perfect. So comfy, lightweight enough for the warmer day, easily layered when it got chilly. I got so many compliments. It’s a Minnie chic piece!

Dress by Caroline Constas

vintage scarf

Bobby’s jacket (but Mother makes a great one for women!)

Calzedonia tights (they’re amazingly durable!)

handmade beret

old ballet flats

Oh My Disney bag

I’m not sure which is prettier: Cinderella’s castle during the day, or all lit up at night! I did miss the spectacle of twinkle lights, but she looks pretty fancy nonetheless. Sorry for the very grainy photos, I had to take these with a super high ISO!

Adjusting to living in Florida — after living in New York for as long as we did — has taken some time. But I’m very, very glad to be near family. And closer to Disney? An added bonus. We got Florida resident annual passes, so luckily there will be lots more Disney for us in the future. If we are going to miss out on seasons, we will take Disney magic as a very nice consolation prize.