Disney Vacation: My Travel Outfit & What I Wore to Disney World

What To Wear To Disney World is one of my all-time most popular posts, so I figured y’all might want to see what I ACTUALLY wore to Disney World. Today I’m posting my travel outfit along with what I wore to Disney World AND what I packed. (I didn’t wear half of what I packed. #ChronicOverPacker)

Fashion Over 40: Cold Weather Travel Outfit

This is my go-to type of travel outfit. Even in the summertime, airplanes can be cold, so I usually wear jeans and a sweater or jacket with a short sleeved top underneath so I can remove my jacket when I get to my destination.

Fashion Over 40: Cold Weather Travel Outfit

I chose my layered utility jacket from American Eagle Outfitters because it’s a nice weight for colder weather without being too heavy for the airport. I wore it with a short sleeved t-shirt, cropped skinny jeans, and Pumas. On the way home, I wore the same jacket and jeans with a grey t-shirt and my Converse.

Fashion Over 40: Cold Weather Travel Outfit

I carried this lightweight snakeskin satchel, although I wouldn’t recommend it due to the lack of a zipper. I didn’t think about that until I got on the plane, but I prefer a bag with a zipper so I don’t have to worry about my junk falling out when it’s stowed under the seat in front of me. I also try to carry a bag that is made out of nylon or cotton or some type of durable cloth because it isn’t as heavy as leather and you don’t have to worry about it getting scratched going through security.

Fashion Over 40: Cold Weather Travel Outfit

I highly recommend one of the Stella & Dot Getaway Bags. I’ve carried mine in the past, and it is perfect for plane travel.

Fashion Over 40: Cold Weather Travel Outfit

For jeans, I wore cropped skinnies because I knew they’d be good for evenings or cooler days at the Disney parks in addition to my travel days. The Puma Suede Classic sneakers are the perfect marriage of comfort and style.

This turned out to be the PERFECT travel outfit for Disney in the wintertime. I felt put together and comfortable in the airport, and when we arrived in Florida, I just removed the jacket and I was ready to hit the parks!

Fashion Over 40: Cold Weather Travel Outfit

Outfit Details: Striped Vintage Tee, $24.99 + 40% off (I’m wearing a medium) | similar cropped jeans, $159 (mine are Hudson) | S&D Engravable Disc Necklace, $69 (earn Dot Dollars!!) | Puma classic suede sneakers, $59 | bag (old; I recommend a Stella & Dot Getaway Bag)

What I Packed

First, let me make this disclaimer. If you’re looking for minimalist travel advice, this is definitely not the blog for you. I have learned over the years that I am much happier when I over pack. Whenever I try to pack lightly, I regret it, so now I just pack everything I think I might need. I always check my bag(s) through to my final destination so I don’t have to fuss with them on the plane.

Pardon the poor photo quality, but I took this picture when I was packing to go home, and it’s the best I could do with the lighting in our room. It was a 5-day trip, and two of the days were mostly travel, so this is definitely overkill. I like to have choices, what can I say??

What I Packed for 5 Days at Disney World

Clothes: I packed 1 dress, 7 short sleeved/sleeveless tops, one pair of jean shorts, one pair of cotton twill shorts, and an extra pair of jeans. I also packed a lightweight cardigan and an extra sweatshirt plus my bathing suit and cover-up.

I thought the extra jeans were unnecessary, but I ended up wearing them twice and the jean shorts once, and then I had my cropped jeans for the 2 travel days, so it worked out. I never wore the twill shorts. I did wear the dress to dinner one night, though. It’s from Athleta, and it’s made of moisture-wicking material that is stretchy and comfortable but never loses its shape. It’s PERFECT for travel. I also spent a few hours by the pool one day, so I did get to use my swimsuit. I didn’t pack workout clothes because you walk so much at Disney World, I never feel the need for more exercise. As it is, I lost 2 pounds in 5 days. Crazy, right!?!

Shoes: In addition to the Pumas I was wearing, I packed my new Converse, my favorite ballet flats, and my Orthaheel sandals. I picked up the running shoes in the airport because I panicked and worried that I’d need them. See, even when I over pack, I still usually wish I’d brought one more thing!

Jewelry: I only brought a few pieces of jewelry — a pair of gold earrings, a pair of silver earrings, a silver bracelet, and my silver Alex and Ani pendant. I wore the gold disk necklace, gold Alex and Ani bangles, and diamond studs on the plane.

Bags: I packed a small crossbody bag to carry in the parks. Unfortunately the strap broke the first day, and I had to tie it up and carry it as a shoulder bag, but otherwise it was PERFECT for park days. I got mine at Ross, but this is similar. I highly recommend carrying something like this unless your kids are younger and you need something bigger. In that case, a lightweight backpack is a great solution.

And yes, I DO have pictures!! If you follow me on Instagram, you probably already saw most of these. My daughter took my outfit pictures with my iPhone, so the quality is so-so, but you can get the gist.

What I Wore

The night we arrived, we got settled into our suite, and then I changed into those running sneakers to go to the Magic Kingdom for Mickey’s Very Merry Christmas Party. They worked well with the navy and white striped top and my cropped skinny jeans. I rolled the jeans into a single cuff so more skin around the ankle area was exposed, hopefully creating a slimming effect! I don’t have a picture, though.

Day 1: Ramones tee (sold out), cuffed jean shorts (options here), Orthaheel sandals (similar), crossbody bag (c/o Ross; options here, here, and here)

We spent our first full day at Disney World in the Magic Kingdom. I wore this easy, casual outfit, and it was perfect. My feet did just fine in the sandals. I’ve done a lot of walking in them, and I knew they’d give me the support I need while still looking cute.

What I Wore to Disney World

That night, I changed into my Athleta dress for the Hoop Dee Doo Review. I didn’t get a picture, so I’ll borrow one from last summer. Like I said, the moisture-wicking material and stretchy fabric is perfect for travel. It looks nice without feeling fussy. This one is sold out, but Athleta is always a great place to look for this type of dress.

What I Wore to Disney World

Day 2: navy and white sleeveless top (old), Emma skinniesConverse, and a white cardigan (old)

I wasn’t sure how well I would do in the Converse all day, so I tested them out at breakfast. We went over to the Contemporary and ate at The Wave. They are fine except they don’t have much support, so before we went to the Animal Kingdom for the rest of the day, I switched to those running shoes I bought at the airport. I double cuffed the jeans for more ankle exposure, and I felt like it looked cute. Thanks to the “Athleisure” trend, it isn’t such a fashion faux pas to wear running shoes with casual outfits anymore. Now it’s all about making the proportions work for you.

What I Wore to Disney World

Day 3: magenta tulip top (from LeTote), Emma skinnies, Felicia Flats, crossbody bag (it broke, so I had to tie off the strap and carry it on my shoulder)

Once again, I didn’t wear the ballet flats all day. They are super soft and felt great on my tired feet, but I knew they didn’t have the support I’d need to get me through a long day at Epcot, so I switched to the Orthaheel sandals after breakfast. My podiatrist is always telling me to change my shoes 2 or 3 times a day, so that is what I did!

What I Wore to Disney World
To fly home the next day, I wore the cropped jeans again with my grey V-neck tee and my Converse, and I carried my jacket. I definitely was glad to have it on the plane. Brrrr.

That black bag you see falling over on the floor behind me is my laptop bag, so I actually had 2 carry-on bags with me in the airport. I could definitely have consolidated, and sometimes I do, but this time I just carried both.

What I Wore to Disney World

So there you have it! That’s what I wore to Disney World. I hope this was helpful.

This was a bit of a detour from my 25 Days of Winter Fashion, although this is pretty much what I would wear if I were traveling to Florida in the dead of winter. I might wear full-length jeans and a heavier sweater or sweatshirt, but this basic uniform seems to work for almost any time of year. If it’s really cold, I wear a coat and leave it in the car when I get to the airport.

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