What I Wore On Vacation in Orlando

Paul and I spent a few days in Florida last week, and it was glorious! We were there primarily to see our daughter perform at Disney World with the high school marching band, but we also took advantage of the opportunity for a couples vacation.

You may remember that our 25th anniversary trip to Paris was canceled due to Covid back in April of 2020, and the year before that, we had to cancel a couples trip to Austin, Texas, due to my vertigo. All that to say, this vacation was long overdue!

I always get a lot of requests for vacation looks, so today I’m sharing what I wore while we were there, as well as my travel outfits to and from.

What I Wore On Vacation

SIZING NOTES: I’m 5’5″ and usually wear a small in tops, but I’m in between a 28 and 29 in jeans. My sizes are beneath the pictures, and gifted items are indicated by c/o; everything else I purchased myself.

This was my travel outfit for this trip. I decided to brave the cold weather here at home in favor of arriving in Florida wearing sandals. My feet get hot in sneakers, and I really don’t love traveling in them, even though it makes sense to save that space in my suitcase.

denim jacket (M) // ATM tee (M) // Mother denim (28) // Tory Burch sandals (8) // Evereve necklace // Yurman bracelet // Evereve belt (M) // Delsey luggage

I thought the pink jacket would come in handy in Florida, but I never wore it. I was too hot and humid to need a jacket, but I did get a compliment on it in the airport shuttle, which was fun!

It was a gorgeous day, so we went straight to the pool after we arrived at our hotel, and I didn’t even take time to photograph my pool outfit. I did, however, photograph my drink!

We stayed at the JW Marriott Orlando Bonnet Creek, and the service was top notch. They even set up your beach chairs for you with towels and a headrest. The wait staff was constantly coming by, checking to see if we wanted anything.

I also love that they have two pools — one for the kids and one for the adults, so it was very quiet and relaxing. Just what the doctor ordered!

After a quick nap, I threw on this outfit for dinner. We just went down to the hotel lobby and grabbed drinks and a charcuterie plate at the bar since we ate a big lunch by the pool.

LOFT top (S) // KUT from the Kloth jeans (6) // Vince Camuto wedges (8) // Evereve belt (M) // Loeffer Randall bag // Stella & Dot cuff  // Anthro earrings

I had a photo shoot with a local photographer scheduled for 7:30 the next morning, so I got up early and went down to the lobby for coffee and to send out my daily email before getting ready.

My body doesn’t know how to sleep in, so that is my habit when I’m on vacation. I almost always wear some variation of this outfit for those early morning lobby work sessions.

Athleta wrap (S) // ATM tee (M) // Vuori joggers (M) // TB Millers (8) // Goyard tote

I did a bit of work after my photo shoot before heading back to the pool. We didn’t have anywhere to be that day, so we just hung out at the resort. I intentionally chose a place we could enjoy without having to go anywhere.

pedicure: CND Studio White

Once we tired of the pool, we got dressed and headed over to Disney Springs, and I wore this casual outfit.

This smocked v-neck muscle tee is on sale for $18 at LOFT, and I highly recommend it. It’s true to size, and the 100% cotton fabric has a really nice feel to it.

It’s a fairly simple top, but the smocked detail on the shoulder and muscle tee styling make it a little extra special, so you can dress it up or down.

LOFT muscle tee (S) // Spanx shorts (M) // TB Millers (8) // Gucci crossbody (option) // Evereve necklace // Yurman bracelet // YSL sunnies (option)

We wandered around Disney Springs for a while and then stopped into Jock Lindsey’s Hangar Bar for a drink. That’s a really cool place, if you haven’t been. It was modeled after the airplane hangar dive bar in one of the Indiana Jones movies.

The decor is so cool, and Paul had never been, so I wanted to show him. They have indoor and outdoor dining by the lagoon. We sat outside, of course!

We had dinner reservations at The Edison, but I really wanted to go to Chef Art Smith’s Homecomin’ so we stopped and asked if they could seat us, and they could! I was so excited. Again, the decor and theming is so fun, and the food is all my Southern favorites.

I had the hardest time deciding between the fried chicken dinner and shrimp & grits, so I got one and Paul got the other, so we could try a little of each. We also got the deviled eggs and hushpuppies. So good!

After dinner, we just walked around and listened to live music and enjoyed being outside in the warm Florida weather.

It was quite the contrast from yesterday’s blustery 48 degrees. Now I know why people become “snowbirds” when they retire. I could totally get used to living in Florida for a few months every winter/spring.

The next morning, I did some work, and then Paul and I had breakfast at the hotel. I wore this outfit again (with different jewelry) because I needed him to photograph my bracelets for the Victoria Emerson sale.

I’m really loving these Spanx shorts, by the way. Someone mentioned them in my Facebook Group, so I ordered them to see what I think, and they’re surprisingly good! I like that they aren’t super wide through the thigh, and the pull-on styling is so comfortable.

LOFT muscle tee (S) // Spanx shorts (M) // Baublebar necklace // VE bracelet c/o

Our breakfast was delicious, way above and beyond your typical hotel fare. I was very pleased. I don’t normally eat breakfast, so it really has to be worth it!

After we wrapped up there, we got dressed for a long day at the parks. We bought a one-day park hopper pass for this trip, so we could go to both Magic Kingdom and Epcot.

I just wore a simple white tee and jean shorts. I had planned to wear this tank top, but I got a little sunburned on my one shoulder at the pool the day before, so I decided to wear sleeves to keep that area covered.

My Vejas are the only sneakers I brought with me, and they were fine, but I should have brought my On Cloud trainers. They would have looked just as good and given me more support.

And this bag is my go-to for amusement parks and casual sightseeing. I love all the compartments, plus it’s lightweight and durable. I linked a similar one below.

ATM tee (M) // 7FAM shorts c/o (28) // Veja Esplar (39) // similar HOBO crossbody // Evereve necklace // Yurman bracelet

We had hoped to see our daughter before she performed, but we didn’t make it in time, so we got some ice cream and walked around for a while.

I’m bummed that the professional picture we got in front of the castle didn’t make it to our Disney Photopass account. They scanned the barcode on my park ticket, rather than the QR code in the app, and I guess that didn’t work.

We got one at Epcot too, but those didn’t turn out very good, so I didn’t purchase any. All that to say, this selfie will have to suffice!

We had a while before the marching band performance, so we stopped in to see The Hall of Presidents while we waited. I always enjoy that attraction, and it’s a good way to get out of the sun and enjoy some air conditioning. It was such a hot, humid day.

I have lots of pictures of our daughter marching with the band, but they all include other kids, and the name of her school is emblazoned on the banner she is carrying, so that’s why I haven’t shared any. It was so cool, though.

When that was over, we did the Pirates of the Caribbean ride while we waited for the kids to change and load up the band truck. It was another excuse to get out of the sun and enjoy some air conditioning, and it’s one of the only rides I can tolerate, lol. I get dizzy and motion sick from roller coasters and spinning rides.

After that, we got to see our daughter and her friends for a few minutes before parting ways. Then it was time to hop the monorail over to Epcot.

ATM tee (M) // 7FAM shorts c/o (28) // Veja Esplar (39) // similar HOBO crossbody // Evereve necklace // Yurman bracelet

Man, I’m really looking rough! I didn’t realize my shirt had come untucked. Did I mention how hot and humid it was?

And we had run all over Magic Kingdom chasing the marching band so we could see them perform multiple times. Let’s just say, that was the last day I wore that t-shirt.

We even talked about skipping Epcot and going back to our hotel, but we decided to rally and at least grab dinner there. We wandered through the World Showcase and stopped at the Canada Pavilion to see the Canada: Far & Wide film in one of those circular theaters. We had never seen that before, and it was pretty cool.

I didn’t have dining reservations for that night, but it proved to be pretty easy to get a table for two almost anywhere. We ended up at Chefs de France, and the escargot and Boeuf Bourguignon were excellent. Highly recommend.

We grabbed dessert in Morocco and then took an Uber back to our hotel and turned in early. We’re old, what can I say?

The next day, I wasn’t feeling much like getting glammed up, so I threw my hair into a clip and put on minimal makeup to head over the Universal Studios for the jazz band performance. Thank goodness for big sunglasses to hide tired eyes!

LOFT muscle tee (S) // Wit & Wisdom shorts (6) // Marc Fisher sandals (8) // similar HOBO crossbody // Evereve necklace // Yurman bracelet // YSL sunnies (option)

I got soooo many comments about my choice of shoes. We took an Uber to Universal and just walked down to the Lagoon Stage at Citywalk, where we sat for 30 minutes to see the jazz band perform, and then back to the ride share area to get an Uber back to our hotel. I was fine in these shoes.

While we waited for our Uber, I asked the bellhop to take our picture.

Paul’s Outfit: Goodlife tee (size L) // similar Patagonia shorts // Beckett Simonon trainers

The jazz band performance was at 10:30 AM so we were done there by lunchtime. Citywalk (where the band performed) is free, so we didn’t bother getting tickets to the Universal parks.

Instead, we headed back to our hotel to spend the rest of the day by the pool, and I finally remembered to have Paul take a picture of my pool outfit. I also brought the blue Becca coverup, but I didn’t get a picture of that one.

Robin Piccone tunic coverup (XS/S; also at Zappos) // Prima Donna tankini top & bottoms // Hari Mari flip flops (8) // YSL sunnies (option)

We ordered lunch and enjoyed a few hours by the pool before it was closed due to an afternoon thunderstorm. I just showered off and amped up my makeup for dinner.

It was so hot and humid, and I noticed a few other women at dinner with their hair up in clips, so I was glad I didn’t bother with the whole hairstyling routine.

LOFT tee (S) // KUT from the Kloth jeans c/o (6) // Vince Camuto wedges (8) // earrings c/o // necklace one and two // bracelet c/o

We had reservations at Illume, a swanky sushi bar with a rooftop deck. Unfortunately, the deck was closed due to the earlier thunderstorm, but it was too hot and humid to sit out there anyway, and the indoor seating area was lovely.

Everything we ate there was absolutely delicious, and the presentation was gorgeous. Are you tired of food pictures yet? I hope not, because here are a few more.

This was seriously the most delicious sushi I’ve ever had in my life. Bar none. (And also the prettiest.)

If it sounds like all we did on this trip is eat and drink and sit by the pool, you would be right. That’s my idea of a good vacation!

And that was pretty much our last hurrah, because we were up bright and early the next day to catch a 10AM flight.

I wore the same travel outfit home, except I swapped out the white tee for this grey one. (The white tee was very much in need of a good cleaning, by that point.)

KUT from the Kloth denim jacket (M) // ATM tee (M) // Mother denim (28) // Tory Burch sandals (8) // Evereve necklace // Yurman bracelet // Evereve belt (M) // Away luggage

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70 Responses

  1. Love your”real-life” posts. Happy that you were able to get away, so important to do that – hope you are able to do that Paris trip. We were able to go for a few days in the fall and I had forgotten what a beautiful city Paris is! My husband and I are off on our couple trip this afternoon – a few days in Napa/Sonoma!

    1. I just wrapped up planning a Napa vacation last night! I’d love to know the wineries you’re visiting!

      1. How about we meet you there and do Napa together?! Such beauty and wonderful wines and is a true vacation.

  2. My kind of vacation too! You know I adore pool service and lingering….. that’s vacation!
    We are so alike in this aspect! I’m a minimal packer and I’m guessing by the looks and your luggage this is where we are beautifully different. Lol. Super glad you two got some time away❣️

    1. LOL, I love how positive you are. 🙂 I am not and never will be a minimalist packer. Even on this trip, I was wishing I had brought the white jeans I put back at the last minute. I like to have options! But I was also bringing extra stuff to photograph with Diana. Paul used one side of one suitcase, I and I used the other 3 sections! Worked great, haha!

  3. Looks like the perfect vacay! You and Paul look great! My husband and I are foodies. We always take pictures of our food, even yummy dishes we cook at home. We have actually been having a Spring. Here on the Gulf coast, so many times we go straight to summer. Fortunately we have had cool nights and highs in the 70s. Perfection!

    1. Well, that is nice, at least someone is getting a nice spring! I also don’t like it when we go straight from winter to summer, which happens here a lot — it will be cold until the friggin end of May and then suddenly hot and humid. I’m afraid that is going to happen this year. We might be looking at vacation properties very soon! I’ve been watching Beach Budget Reno (something like that) and they have featured some homes on the Gulf coast. I never considered that area, but it seems really nice.

  4. I love your tote for travel but wondering if you know of any dupes just due to price? All these outfits are perfect for travel. Thanks for sharing. You look like you had a wonderful time!

    1. I know, I hated to link it without any options. I actually looked, and I didn’t see what I wanted. Tory Burch used to make a nice coated canvas tote, and I tried to find it, but I guess they discontinued it. If anyone has any suggestions, please let us know!

        1. I love the goyard tote. Did you get yours on Rue LA LA? I have been thinking of one for a while. Where do they sell them?

          1. Goyard doesn’t sell their merchandise online. There are Goyard stores in large cities like NY, where I purchased mine. At the store they will customize the bag with your initial, hand- painted . I like having the personalization as it shows it’s an authentic bag.

  5. Disney can locate your photo for you. I’ve done this several times. Just give them the date, time, location and what you were wearing and they will find your missing photo. Disney Photopass help (407) 560-4300

  6. Great post – thanks for bringing us along on your vacation. Looks like a great time. The outfits are awesome – and the food looked spectacular!! Glad you had a good trip!! Oh & I have to say, I did giggle over the white T-shirt. Good to know we all really do have the same kind of problems from time to time!!

    Hope your weather at home warms up. I’ve recently moved from the Texas Panhandle to Little Rock, Ar. And it’s been a lot of rainy weather – and cold temps. I’m ready for the sun to shine & to complain about the heat & humidity!! ☺️☺️

  7. Great pics!

    I just bought 3 of the Loft muscle tees. Great basic piece.

    Is Uber the way to go when traveling around? I’m going to Orlando next week (for work). I think the last time I was there was before Uber 😀

    1. Yes, all the parks are set up now with pickup and drop off areas for Uber and Lyft. We use both – I have both apps on my phone, and sometimes I compare, but usually the prices and times are similar. And a lot of hotels have shuttles too. We took the free shuttle from our hotel to Disney Springs and to Magic Kingdom, but we used Uber/Lyft to get back b/c the times didn’t align with our schedule.

  8. What a nice get away for a few days. Do you happen to have a link for the necklace you wore to the sushi restaurant?

  9. With temps in the 40s in Minnesota, this looks like the ultimate vacation! This would be my ideal vacation–food, pool and time with my hubby. Thanks for sharing! I loved the food pics!

  10. Thanks for sharing your couples vacation with us! Your and Paul’s outfits look perfect and the food looks delicious. Since I have really long hair now, I would love to see how you have your hair clipped up in the back. I usually wear mine in a high ponytail since Larry loves it that way, and it does keep my hair off of my neck. But, having another way to clip it up would be nice. It was in the 30’s here this morning, but is warming up into the 70’s with 80’s on the way. Have a blessed day!

  11. This is possibly my favorite type of post. Chatty, newsy but fashion focused. Your blog is my favorite almost every day. I also like complete outfit details which you provide. Glad your trip was wonderful!

  12. This whole post was lovely and so cheerful! As another reader, Sherli, said, I feel like you took us along with you. (I’m in the southern Texas panhandle and the Disney gardens look so gorgeous). Your pictures are great, the travel tips are helpful, and the food photos are great ( I think food is hard to photograph!). I hope many more trips are in your near future!

  13. Great pics – just wondering if you have instructions on how to put hair up with the clip? Mine never looks as good as yours did in t hese pics.

  14. ALL our vacations seem like we plan the next meal at the current meal we are at so I can totally understand sitting by the pool and eating 🙂 – – we glamp so our trips consist of sightseeing and eating (we are normal food foodies – meaning we swear by yelp and are determined to try fun local places that ARE NOT chains). Loved those trainers you had on too.

  15. Jolynne, this was a great post! You look so cute in each outfit, and the food pictures made me hungry! LOL! I would love to know what type of clip you use to put your hair up. My hair is fine so I have a hard time finding clips that stay in and look good.

  16. Love your pics, looks like a lovely place! Also love the ?coral/pink jean jacket, such a pop of color. Looks like Zappos may be out of this color but found what looks similar on another site. Is it actually the coral color? Thanks in advance.

        1. Liverpool also has a gorgeous jean jacket in a mauve color at Northstroms of course. Would also love to have that one as well. Decisions, decisions.

  17. Hi JoLynne,
    A different topic sort of….I’m looking for a slim straight Agolde jean. I have the stratosphere and love those. Are your Dime wash Agolde’s more of a skinny or slim straight? And is the Dime wash the same as the stratosphere?
    Do you have any suggestions for a mid rise, ankle length Agolde jean?
    Thank you!!!

    1. The AGOLDE Toni is a slim straight ankle jean. I love them, but they don’t make the Precipice wash (the one I have) anymore. The Dime wash is similar, but it looks almost acid washed, and I didn’t love it. (I ordered to see how they compared, since I link them so much.) I wish they would do some other colors and washes, b/c they’re good jeans.

      1. Thank you! That helps. Do you know if the stratosphere wash is similar to the Precipice wash?
        And any recommendations/links for a different Agolde Toni to try?

  18. I love this post, including the food pictures 😍
    It’s always fun to see how other people vacation!! Thanks for sharing Jo-Lynne!

  19. Thank you for sharing your outfits and trip! One of my favorite places with so many fun fond memories! We would do a park day then a pool or beach day in between just to rest.. As the kids got older it was nice to go enjoy the parks and sit with a lemonade under a tree! It’s been four years since our last trip as a family and now our daughter is married and we have a granddaughter so going in the future will be like starting all over! And I can’t wait!!!
    Nice to see way you wore to the parks as that was always tricky! Maybe someday if you already haven’t ( other than Epcot )you’ll come to Canada and see some beautiful scenery especially here on the east coast where we are! Very much like parts of Maine! Lots of seafood and the lobster is a must ( even though I’m not a fan salmon is my dish 😉)

  20. Pool + dining out is my idea of the perfect vacay too! And I NEVER get tired of the food pics 😉 Looks like a great time!!!

  21. Jo-Lynne, thanks for taking us along on your trip. It’s always fun to see what outfits you wear, including your travel ones. My husband and I are moving into a new house sometime this spring so travel is off the table until next year.

  22. Loved your outfits and your vacation! Thank you for always being so detailed with the outfit details and giving options, and for being so down- to- earth! It’s refreshing to read a blog that is relatable (I consider myself a young at heart 51 year old).

  23. Would you consider posting Pauls’ dimensions and having him model some mens things? I would love to buy for my hubby and it could open up a whole new line for you? Just an idea…

  24. Love real life posts and these are great ideas for a warm weather vacation pack! I need to pick up/order some hair clips. What’s your favorite(s)?

  25. That’s me….good food, beautiful hotel, relaxing day by the pool and some shopping and I’m a happy girl on vacation; unfortunately I married Indiana Jones, his idea of fun is move, move and move some more….luckily my daughter is grown now so we go off together and hubby and son do their thing.

  26. What great pictures! It looks like you had a wonderful vacation. You always look great in all the outfits you try on. I actually live in Florida a few blocks from the beach and it really is beautiful here. I’m glad you had a good time. Your hotel In Orlando looked wonderful and I agree about all the food being so much a part of a vacation. 🙂
    I wanted to know about the picture of you and Paul posing where you’re both holding an ice cream cone and to ask if those are your real eyelashes?? They look so perfect!!! I’m having trouble with my eyelashes on my right eye.
    They will not curl with my eyelash curler and they just go straight out from my eye!! I have tried everything I can think of and it’s slightly embarrassing. Yours look so perfect and long so I just thought I would ask. Thanks.

  27. That was a great post. So fun to hear about your trip and see the pictures…. Even the food. Lol. I’m so ready for a vacation. It’s been too long. Always be thankful you can eat out and enjoy so many different foods. I struggle with multiple food allergies and it’s taken that away from me. I miss vacations of enjoying the different restaurants. You do a good job of packing. It’s hard. I want to take too many shoes etc. Thanks for sharing your trip.

  28. Your blog is my favorite! My husband and I also love to eat lol. I know what you mean about drastic weather changes. When we left home in South Louisiana this morning, it was 66°. When we arrived in Texas Hill Country this evening, it was 98°!!

  29. This post was so helpful! I’m heading to Orlando with my daughter this summer and since we live in NY we need to pick up a few more Fl friendly clothes and shoes. Would love to know if you have any recommendations for sandals to wear to the parks (since it would be too hot for sneakers). XO Nipa

  30. I was in Orlando April 18-21 with my grown daughter. We had so much fun together; I spent more time with her in 2 days than in the last year and we live only 20 minutes apart!! Stayed @ Disney All-Star Music which was very adequate but not the Marriott. We had 2 day Park Hopper passes and did all 4 parks in 2 days. Tired feet for sure; I was proud of myself for keeping up (I’m 65 and she is 30) and I think she was more sore than me at the end of our day! Ha! Love all of your outfits. Inspired for Tampa in August!

    1. That’s where my daughter stayed with her school! You just missed her, lol. She came back in the 17th. So glad you had fun. She loved the resort

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