Style Guide for 5 Days at Disney World

Disney World isn’t just for kids (and neither are the Mickey-shaped snacks)! My 26 year old daughter Emily LOVES Disney! When she booked a trip for herself, I nudged my way in and went with her! I wanted to spend time with her, and see what her love of all things Disney was all about. Our trip did not disappoint! We packed a lot of fun (and a lot of steps!) into our five days. And ~~most~~ all of the credit goes to Emily for planning our days, knowing her way around the parks, and figuring out how to work the Genie+ system for speedy ride access!

Before I begin, let me say…I highly recommend traveling with your adult children. There’s something special about experiencing destinations together, particularly when those places hold a special significance for them. Whether it’s a city they’ve always wanted to explore, a country they admire, or a magical theme park, sharing these experiences can strengthen your bond and create unforgettable memories. Plan a trip with your adult children to the places they love—you won’t regret it.

Whether it’s Disney or someplace else this summer, I hope this style/travel guide gives you some ideas for how to pack for your next warm summer adventure. When you’re over 50 and want both comfort AND style, these outfits will work for you!

Note: You loved this post so much, so it’s been updated for 2025 with some fresh links and new ideas! In some cases, links are not exact matches because items have sold out, but I’ve included similar styles from trusted brands.

Our Disney World Adventure

Before we get to the styles, here are a few details about out trip.

Getting to Disney World

We booked a 6:30 a.m. direct flight from the DC area to Orlando to maximize our time with a full day there on our travel day. Once there, we hopped on the Mears shuttle bus for transportation to our hotel. The shuttle bus is the most convenient way to get to and from the airport. Booking with them is very easy, and it’s much affordable than an Uber (only $16 each way).

In the past for family trips, we have stayed at the Contemporary Resort and the Boardwalk Inn Resort. The Contemporary is beautiful, with a monorail stop in the hotel lobby and convenient walking to the Magic Kingdom–but all that convenience has a hefty price! The Boardwalk Inn is also beautiful and it is walking distance to the entrance to Epcot.

Where We Stayed

For this trip, we stayed at Emily’s favorite hotel, the Pop Century Resort. Each section of the hotel is themed with decor from a different decade, and we stayed in the 1950’s section. This is one of Disney’s “value resorts,” but we found the room to be very comfortable and perfect for our five day stay. The Pop Century Resort is conveniently located by the sky-liner for easy park access to Hollywood Studios and Epcot. You can use a shuttle bus for a 20 minute ride to Magic Kingdom or Animal Kingdom.

Our hotel wasn’t ready when we arrived, so we checked our bags and headed over to Disney Springs for a relaxing, delicious lunch at The Boathouse (Emily’s first stop on every trip) and an afternoon of shopping. Disney Springs has all of your favorite Disney merch in one place. And it also has all of your favorite retailers, like lululemon, Zara, and Tommy Bahama, in case you forgot to pack something. Plus many of those retailers feature Disney exclusive collections.

For our return trip, we maximized that travel day as well, booking a 6:45pm flight, allowing for plenty of last-minute park time, one last Mickey-shaped snack and a little last-minute shopping. A quick change in the hotel restroom, and we were back on the Mears shuttle for the flight home. Five days was PLENTY of time at the four Disney Parks, and by maximizing those travel days, you could do the trip in four days.

My Disney World Mix-and-Match Outfits | Over 50 Style

The “what to pack” part of a Disney trip is almost as fun as the vacation itself!

Emily likes to create her outfits with subtle nods to her favorite characters, matching her themed Disney ears and adorable backpacks with some everyday athleisure dresses, shorts, tanks and tees. Her favorites for this trip were her tanks and skorts from CRZ Yoga on Amazon. You can see more of her outfit ideas on her Disney IG account.

I packed in a mix-and-match theme, with classic black, white and red for Minnie and Mickey Mouse–I also wanted pieces that I could wear beyond our Disney trip. This is an easy way to dress for Disney because so many sites have cute, inexpensive, Disney t-shirts. Check Etsy, Target, Amazon and Kohls for under $25 options. Plus, you probably already have a lot of the black and white basics. Once you find your shirts, add your favorite skorts/shorts, and voila! You’re ready for Disney! Or better yet, find an assortment of athleisure dresses you love–that will make your packing a breeze! Here’s a sampling of how I packed.

Once I planned my outfits for each day, I also packed some extra solid white t-shirts (my favorite from J.Jill was perfect for this) and Athleta tank tops in black and white–in case I needed to change mid-day.

Here is what I packed for five days:

3 skorts
3 t-shirts (plus a few extra t-shirts and tanks)
2 dresses (plus 2 extras that I didn’t end up wearing)
shape wear shorts for each dress (a must-have for your thighs!)
5 sneakers/sandals (more on that later!)
10 pair Bombas socks

Packing tip: If you are visiting Disney when it is warm, pack extra! Chances are you will get sweaty, and a mid-day break at the hotel with an outfit change will be a welcome refresher!

SHOP DISNEY STYLE

For our trip, the temps were already in the 90’s (with the “feels like” temps around 103), and the favorite thing I packed was a Zella athleisure dress from Nordstrom. If I had known how great it would be, I would have just packed five of them! For my next trip, dresses will definitely be my preferred option! I linked a few others above that I love for travel.

What not to wear for Disney? I’m not a fan of denim in the park, especially when it’s warm. The denim doesn’t breathe and it rides up as you’re walking. I prefer skorts or dresses with some very light/thin shapewear shorts underneath. And if you’re opting for athleisure shorts, just get them long enough to avoid any thigh rub–it happens to everyone in the heat!

Find the Perfect Park Bag (and What to Carry in It!)

Going to an amusement park without young kids is liberating because you can finally pack lighter! My bag contained the bare essentials and I added an Apple Air Tag in case my bag got left behind.

For this trip, I used this crossbody bag by shortyLOVE. It’s a great travel option. Emily prefers the cute backpacks by Loungefly, and they are definitely a popular choice throughout the parks (plus they hold a lot more than you think). If I went to Disney more, I would definitely get a Minnie backpack, but I wanted to buy something I could use again after Disney. I swapped my crossbody strap for this under $10 strap from Amazon giving my bag a Minnie vibe.

Don’t forget the little extras that make park life easier–some of our favs include the carabiner water bottle holder, Touchland hand sanitizer, a MagicBand holder, a phone charger, and a handheld fan.

Update for 2025: This slingbag would be my new preferred bag, or a loungefly Disney backpack. We also discovered these water bottle clip holders, below, to attach our bottles to our bags – super convenient!

SHOP DISNEY PARK BAGS AND ACCESSORIES

The Best Shoes for Disney When You’re Over 50

Yes, friends, that’s over 24,000 steps on my Apple Watch! That makes your shoes the most important thing you pack for Disney!

Like most of us “of a certain age,” I’m prone to plantar fasciitis, and I was worried about my feet holding up to a five day Disney trip. Averaging 20,000 steps a day, your shoes need to be ~~good~~ great! I brought these shoes with me (I was fully expecting my feet to be a problem!! thankfully, they were not!) and here are my reviews:

FitFlop Rally Knit Sneakers – This is my top pick! These were BY FAR my favorite sneakers for the trip. Fashionable AND comfortable. I definitely recommend them not only for your vacations, but for everyday wear. They’re so cute with dresses and skorts. They also come in a leather option.
B rooks Glycerin 20 Neutral Running Shoe – also a top pick! These were my backup pair that I switched into for the last day.
Adidas Supernova R unning Shoe – I wore these for traveling, and they were a backup pair in case one of the others didn’t workout. I’d say these are a good option for shorter walking days, but if you have a mega-day planned in the parks from open until close, these wouldn’t be my first choice.
Keen Elle Backstrap Casual Platform San dals – I bought these after seeing them recommended on a bunch of Disney blogs. They were a nice option for an evening at Hollywood Studios, but not what I would consider an all-day shoe, and I was kinda grossed out about having my feet exposed in an amusement park–how did I ever do Disney in flip flops once??? Stick with sneakers!
Oofos OO lala Sandals – I always bring flip flops on vacation. These Oofos are made for recovery, and were especially great to wear in the room after a day in the park or for a quick trip to the gift shop for a snack.

Pro tip: If it’s hot enough to change outfits mid-day, then chances are your feet are sweaty, too, so a mid-day sneaker change is a great idea to avoid blisters.

Don’t forget the socks!

Those are just as important as the shoes, and I definitely recommend these cushioned no-show socks from Bombas. They were perfect for the FitFlop sneakers, and did not slide down as I wore them. For a no-show option that stays put, Bombas for the win!

SHOP DISNEY SHOES

Capture the Memories with Your Adult Kids

Traveling with your adult kids is a fun and special time. So remember to get lots of pictures from your trip! At Disney, the best vacation investment you can make is the Memory Maker plan for unlimited park pictures. Everywhere you go, you’ll see photographers in all the iconic locations. Once they take your picture, they scan your MagicBand and the photos are added to your account (same for photos taken on the rides). It’s the best way to get pictures together without taking selfies or asking random people. Pro tip: If you do need to ask random people to take your picture, the easiest way is to offer to take a picture for them, too!

Check the Epcot calendar–they have so many festivals happening. The Flower & Garden show was in full swing when we were there in May; the art festival was happening on a January trip.

Favorite Hotel: The Contemporary is our favorite place to stay, but the location and convenience come with a hefty price. The Pop Century was a great affordable alternative, with convenient access to Epcot and Hollywood Studios via the sky-liner.

Best Place for Breakfast: Sleepy Hollow in Magic Kingdom has a delicious fresh fruit waffle sandwich (served with strawberries, banana, blueberries, and chocolate-hazelnut spread).

Best Lunch/Dinner: A trip over to The Boathouse in Disney Springs is worth it for a great meal! It’s how Emily starts every Disney vacay!

Best Ice Cream: After a long day in the park, the hot fudge sundaes at Storybook Treats really hit the spot! There are a lot of fancy ice cream treats at Disney, but this classic was perfect after a long day when we were exhausted!

Magic Kingdom Favorite Rides: Mine Train, Haunted Mansion

Epcot Favorite Ride: Ratatouille

Animal Kingdom Favorite Ride: Avatar Flight of Passage

Hollywood Studios Favorite Rides: Slinky Dog Dash rollercoaster, Mickey and Minnie’s Runaway Railway, and Star Wars: Rise of the Resistance

Favorite Time of Year to Go: According to Emily, if you’re not limited by school calendars anymore, the best time of year to go is early January–cooler temps and fewer crowds/lines.

Favorite Non-Ride Activity: Pin Trading! Start with a couple of mystery packs in a collection you like,. When you get dupes in your packs, trade those for new ones. It’s a great way to strike up a conversation with a cast member and learn something new about Disney. It’s also fun souvenir to collect pins for the parks you visit, the special events you attend and the hotels you stay in.

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Style Guide for 5 Days at Disney World