It’s the holiday season! And it has been since November 1st — at least at my house and at Disney World. People have teased me for years about how early I decorate for holidays (mid-august for Halloween and 11/1 for Christmas) and my response is “I set for Christmas when Disney does.”

With that bit of background info, it’s not surprising that I started looking for holiday-inspired clothing and accessories in late October. And I’m so happy I did! A tip? Small Shops — like the wonderful ones featured in this post — need time to create and ship your unique orders, so don’t procrastinate, or you’ll wind up on the naughty list! Just kidding, but you may end up rushing to wrap.

I made reservations to visit Magic Kingdom on November 6th — the first day of full-on Christmas magic. And magical it was. In 2020, everything is different, and at Disney World, that means no Mickey’s Very Merry Christmas Party — a separately ticketed event with special holiday performances, treats, and meet and greets. Instead, Disney has opted to spread a little holiday joy all day, every day through random cavalcades featuring characters in their holiday wear! Even Santa makes appearances throughout the day!

Hearing Christmas music on Main Street USA is perhaps the happiest thing. I’d argue that if you had a bit of pixie dust, and thought of that memory, you’d fly straight to Neverland. Add to that, holiday treats and an all-around atmosphere of festivity and you might forget it’s 2020 after all. Of course, masks and social distancing are required as always. (You’ll see my favorite Shop Disney masks in the photos below!) During my visit, I brought a few outfit changes, like I always do!

I get commission for purchases or clicks made through some links in this post.

First Outfit: Home for the Holidays

Fun fact, I’m from Michigan! So I can’t really say that Orlando is my “home.” Especially not my “home” for the holidays. My whole family is still in Michigan, and Theo’s (my husband) family is mainly in France. But the two of us met here at Disney (on my college program) so it felt like a home of sorts. We tried to live in Michigan for two years, and while I LOVE my beautiful home state (especially covered in snow) I missed the parks too much. So, I’m very grateful to spend the beginning of the holiday season here at this “home” and hopefully, the last week home with family in Michigan!

I started my day in this casual, festive look! When I’m outfit planning, I wear the outfit most likely to wrinkle first. That way, I don’t have to worry about throwing it in my bag after I wear it.

This top is a raglan from The Family Shop. I love their style and the bright colors perfectly suit me! I paired it with this denim tiered skirt from Aerie, faux leather ears from Park Hopper Design, and these adorable candy-cane Mickey pom earrings (gifted) from Luna and Co (use code: Mal15 for a discount).

My friend and I spent the morning taking some photos, saying hello to some friends we ran into, and taking in the Christmas decor. We also headed to It’s A Small World for the first ride of the day!

After that I was getting warm and was ready to change into outfit number two!

Shirt | Skirt | Mask | Ears — Sold Out | Earrings 

I get commission for purchases or clicks made through some links in this post.

Second Outfit: Jingle Cruise

For my next outfit, I kept the same skirt on! It’s an easy way to save space in your bag, and still switch it up! I swapped the longer sleeves for a cooler option. When I saw this tee on www.polkadotpixieshop.com, I HAD to have it. Adventureland is my favorite land — our first Orlando apartment was Adventureland themed — so I love the holiday overlay of the Jungle — I mean, Jingle — Cruise!

The details are so fun! I was also highly inspired and did this little Jingle Cruise illustration to share with the photo. Have you been on the Jingle Cruise? If not, you can look it up on Youtube and get a fun little POV ride-through!

By the time we made it over to Adventureland, the line was fairly long, winding around the land, and we were hungry! Unfortunately, we didn’t get to ride it that day, but I will 100% get on it at least once this season. I rode it several times last year!

We instead opted to head over to Sleepy Hollow in Liberty Square on the hunt for some Mickey Waffles. I thought that they might have gluten-free options (they did not) so I can’t make a recommendation, but the waffles looked very yummy!

I get commission for purchases or clicks made through some links in this post.

Third Outfit: Santa Baby

Another outfit-change tip: save your favorite outfit for last! That way, you can wear it the rest of the day! This romper — yes, you read that right, it’s a ROMPER — is my favorite piece of clothing right now. It’s beautiful, with little embroidered flowers all over it and a flattering cut. It’s also very comfy and functional, since it has shorts! I love wearing this to the parks because rides? No problem. Twirling to Christmas music on Main Street? No problem. You can find it here.

I paired it with a red beret (a gift from my mother-in-law in France), this bow belt from amazon, and a pair of red tights for a Santa-inspired look. I also switched to the gingerbread face mask from Shop Disney.

Whenever you’re headed to the parks, make sure to pack extra masks. It feels so good to put on a fresh new one after a few hours in the old one. Even this time of year, it can get hot and a sweaty face mask is no fun.

I bought two holiday ones from Shop Disney, the gingerbread one and the Minnie joy one, both a size large. Disney is making their masks with a new fabric that’s much more comfortable! I’ve also had less mask-ne from these new fabric masks than from the previous type!

Another great option for fun Disney-inspired masks is That’s Sew Cotton! Most of my masks are from them, made to size!

I hope your holiday season is off to a wonderful start! Let me know if you’re headed to Disney World this year or not! Follow along on my instagram @mallory.drew for theme park and Orlando magic and adventures!