What to Wear on Vacation

Who has vacation plans coming up? With Easter less than a month away and summer on the horizon, it seems like everyone is going somewhere fun, so I thought I’d do a roundup of outfits for warm weather vacations in case you need some packing inspiration.

And of course, any of these outfits can be worn at home as well… if it ever warms up, that is!

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

What to Wear on Vacation: Sightseeing

I wore this exact outfit sightseeing in St. Augustine last month. It felt a little fussy when I left my hotel room, but I felt cute and pulled together once we were there, and it was also perfect for going out to lunch at the Columbia Restaurant.

Unfortunately, the woven wrap I’m wearing sold out rather quickly, but here’s a link to more wraps and dusters by the same designer. Also, these shorts are spendy, but they are soooo comfortable. Soft and stretchy, and they have a really flattering fit and a 4″ inseam. They’re the only shorts I needed while I was there.

Harriet Isles wraps // Z Supply tank c/o (M) // 7FAM shorts c/o  (28) // Tory Burch sandals // YSL sunnies (budget option) // Evereve hoops  //Evereve bracelet // Evereve necklace

What to Wear on Vacation: Family Dinner

I love this simple outfit for dinner out with the family while on vacation, if it’s a mild night. This sweater would also pair well with white shorts for a more casual venue.

Also, these jeans are 25% off at Bloomies! I sized up to a 29, but last year I probably would have bought the 28, so they’re TTS or size up if in between.

LOFT sweater (size S; similar option) // Mother denim (size 29; similar for less) // Dolce Vita mules c/o (size 7.5; also at Bloomies) // hoops c/o Evereve // Kendra Scott necklace // old Stella & Dot bracelet // Coach handbag (also at Nordstrom) // rag & bone sunnies

What to Wear on Vacation: By the Pool

My idea of vacation is long lazy days by the pool, and this coverup is perfect for that. The casual style suits my aesthetic, and I appreciate the chest coverage.

In fact, I like it so much, I also got it in the Orchid, which is on sale at Nordstrom. (Both my Waterfall Blue and Orchid are on sale at Zappos.) I ordered the XS/S and the MD/LG to try because I was unsure of the fit, but the XS/S was plenty roomy.

coverup dress (XS/SM) // Havaianas flip flops (7/8)

Also, these DIFF sunnies are lightweight and comfortable with polarized lenses, and priced under $100.

R coverup dress (XS/SM) // Havaianas flip flops (7/8) // Brighton tote // Vera Bradley beach towel // DIFF sunnies // Prima Donna tankini & swim briefs

What to Wear on Vacation: Shopping

This classic look will take you so many places, but I immediately thought of an afternoon perusing some upscale shops. I love the Granite Blue of this top paired with white denim, but there are other colors available.

These jeans are currently on sale at Bloomies, and these wedge sandals are on sale at Macy’s. They’re comfortable enough for a few hours of walking. The jeans are TTS, or size up if in between, and definitely size up half in the wedges.

BR Factory top (S) // Mother denim (size 29; similar for less) // Vince Camuto wedges c/o Evereve (8) // Loeffler Randall bag // Stella & Ruby necklace // rattan earrings // Stella & Dot bracelet // rag & bone sunnies

What to Wear on Vacation: Lunch with Friends

The tencel material in this jumpsuit is super soft and lightweight, very comfortable. It also packs down to almost nothing in your suitcase.

I was worried about using the bathroom with the buttons and the tie waist, but it wasn’t a big deal. You could also cuff these and wear them with flat sandals for a more casual vibe.

Cloth & Stone jumpsuit c/o (size S) // Dolce Vita mules c/o (size 7.5; also at Bloomies) // Coach handbag (also at Nordstrom) // Baublebar earrings // Baublebar necklace one & two // bracelet c/o

What to Wear on Vacation: Casual Dinner

I wore this outfit touring St. Augustine with flat sandals, and I threw on the wedges for this picture to show another option. You could also swap the shorts for white jeans to level up the look a bit more and get more use out of the wrap.

This tank is an easy base layer for lots of outfits, but it runs very small; definitely size up, especially for larger chests.

Harriet Isles wraps // Z Supply tank c/o (M) // 7FAM shorts c/o  (28) // Vince Camuto wedges c/o Evereve (8) // YSL sunnies (budget option) // Evereve hoops  //Evereve bracelet // Evereve necklace

What to Wear on Vacation: Day at the Beach

This is the same swimsuit I was wearing above, just with a different coverup, and it looks like a whole new outfit!

This beach bag is larger than the Brighton one, and it holds a lot, making it perfect for a day at the beach when you won’t be close enough to run back and forth to your hotel room or beach house. It lays flat in your suitcase so it doesn’t take up any room to speak of, and it can double as a tote for a casual dinner in the evening or a day of sightseeing.

Robin Piccone tunic coverup (size 4-6; also at Nordstrom) // Tory Burch sandals (8) // Hat Attack tote // DIFF sunnies

This coverup is a little dressier than the R tank dress, and it also comes in black. Since I wear coverups so much in the summertime by our backyard pool, I bought both colors.

Robin Piccone tunic coverup (size 4-6; also at Nordstrom) // Tory Burch sandals (8) // Birdsong tankini top & bikini bottoms // DIFF sunnies // Amazon bracelets // Hat Attack tote // Madewell hat

What to Wear on Vacation: Fancy Dinner

I wore this comfy jumpsuit with the cognac wedges and more casual accessories to dinner with friends one night in Neptune Beach, but I dressed it up for this post, the way I’d wear it for a destination wedding or a fancy dinner with Paul.

Michael Stars jumpsuit (S) // Sam Edelman sandals (8) // Coach handbag (also at Nordstrom) // Stella & Ruby necklace (also at Verishop) // rattan earrings // Stella & Dot bracelet // YSL sunnies (similar for less)

Here’s the more casual version of the look.

Michael Stars jumpsuit c/o (S) // Vince Camuto wedges (8) // Loeffler Randall baguette bag (similar) // earrings // necklace // bracelet

What to Wear on Vacation: Date Night

Okay, I’m running out of things to do on vacation, but let’s face it, you have to eat dinner every night, so here is another dining option with white denim.

This is a different pair of white jeans than the ones shown above, but of course the same white jeans would work for all of these outfits. No need to pack more than one!

Also, this tank is currently on sale. It comes in a bunch of solid options that make nice layering pieces, but I love this print for a stand-alone top. It has a double v-neck, making it a little more flirty and fun than your typical tank, perfect for a date night at home or on vacay.

printed tank (S) // Frame denim (28) // denim jacket (S) // Sam Edelman heels (size 8) // Coach handbag (also at Nordstrom) // YSL sunnies (budget option) // old hoops // old bracelet // chain necklace // pearl necklace

What to Wear on Vacation: Evening on the Beach

Evenings on the beach can get a bit nippy, especially at the Jersey shore, so I like to have a long-sleeve sweater or cardigan to throw on with shorts. This look is so beachy-chic, I just love it!

This outfit will also come in handy in Maine this summer, and even for mild evenings here at home by the pool with friends.

525 Cotton Cable Vneck Pullover c/o (S) // 7 For All Mankind Midroll Short Destroy c/o (28) // similar sandals // Baublebar earrings // initial necklace c/o // stone bracelet c/o // Hat Attack tote // DIFF sunnies

What to Wear on Vacation: Destination Wedding

So many have asked about an outfit to wear for a beach wedding. I have not been to one, so it’s hard for me to gauge if this would work or not, but it would certainly work for an afternoon wedding in a resort location… or anywhere, really.

It’s not formal enough for cocktail attire or black tie, but it is perfect for any type of semi-formal or “dressy casual” wedding in the spring/summer months. I’m actually thinking of wearing it to church on Easter Sunday, if it’s warm enough here.

Maggy London dress (size 6) // Sam Edelman heels (size 8) // Coach handbag (also at Nordstrom) // similar Kendra Scott earrings // Kendra Scott necklace

What to Wear on Vacation: Travel To & From

Finally, if you’re going on vacation, you have to get there, and figuring out your travel outfit can be tricky. It’s nice to wear things you can actually use when you get to your destination, but it doesn’t always work out that way.

I did wear this exact outfit minus the utility jacket, and with sandals rather than sneakers, for an afternoon of shopping and walking on the beach at Sanibel Island last April. I didn’t get much use of it during my trip to Ponte Vedra last month, although I did wear it to lunch at our resort the day we arrived and the day we left because I had it on for traveling.

ATM t-shirt (M; option) // Mother denim (29) // P448 sneakers (39) // similar AllSaints belt (M) // Madewell earrings // YSL sunnies (budget option) // Evereve necklace // Goyard tote // Away luggage

Still, there’s not much else you can do when you’re traveling from a colder climate to a warmer one. You may have to wear a few things that won’t be necessary once you reach your destination.

Here’s the look from last year, in case you want to see that. It was only about 70 degrees that day, so I was perfectly comfortable in jeans.

ATM tee (M; option) // Mother denim (28) // similar sandals // similar Hobo crossbody // Kendra Scott hoops // Gucci sunnies (budget option) // Lagos bracelets

I often wear joggers with a t-shirt and jean jacket when I travel. This outfit works out well because I wear the joggers in the mornings before I shower and get dressed, and the denim jacket usually comes in handy with dresses and white denim outfits. This is what I wore last year to and from Florida with the family for Easter.

I also wore my running shoes, so they didn’t take up valuable packing room. This outfit is more practical, in that I wore everything I’m wearing here at other times during my trip, but I felt more pulled together and stylish at the airport when I was wearing the jeans and utility jacket outfit above.

denim jacket (S) // grey tee (M) // Vuori joggers (M)  // Brooks sneakers (9) // sunnies // Away luggage // LV Neverfull MM

I hope that’s helpful! I know I’ve shared all of these looks before, but I figured it’s nice to have them all in one place.

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17 thoughts on “What to Wear on Vacation

  1. Just a suggestion, but I would love to be able to “pin” some – ok lots – of your outfits for inspiration to my Pinterest board, so I can find them when I need an outfit idea. Thanks for all the inspiration you provide. Have a great week.

    1. Jenice, when I’m on my mobile, I can hold my finger on the photo, then a menu pops up. I can then pin the photo to Pinterest . Not sure how it works on a computer. Hope that helps!

  2. This all look great! Thanks for compiling this looks; will definitely Pin them on Pinterest for future reference. You look terrific in all the outfits. The dress is gorgeous; perfect for Easter. Florida looks so beautiful! Haven’t been in yrs; will have to return! What happened to your anniversary trip to Paris? The one that was canceled/ postponed due to COVD? Did you folks decide to do Florida instead? Have fun! Look forward to those posts.

    1. Well, we still have that credit on an apartment in Paris. It’s good through 2022, so we were thinking of planning it for fall, but with the state of the world right now, I don’t know if we want to pursue it. I hate to plan another whole trip, only to cancel once again if we end up in WWIII. And they’re talking about another Covid variant? Jesus, take the wheel! LOL

      1. Jo-Lynne…..I totally get your thoughts on your Paris trip. Maybe you could still plan it last minute. You are so good at planning, and I’m sure you have most of it figured out from the last planning. Just wait until closer to Fall and by then I’d think we’d know what is going on with the War etc. Yes, they keep talking about the new variant, but then in another breathe, the news says numbers are way down and still going down. I didn’t watch the Oscars last night, but while flipping through channels, I saw them and I told my husband that it sure didn’t look like covid was still going around. Sooooo many people gathered together. I guess if you have someone still affected by it, it would feel so, but I think in most places, people are moving on. I live in Oregon and I’ve heard we have comedians making fun of Oregon and Wa. that we are still playing covid, while the rest of the states have been done with it for over a year. Sometimes it would be nice to live in the midwest, as I live an hour from Portland Or. and they won’t take off their masks etc. The mandate has been lifted as of mid March. I live in a small town, so things are doing well here. I look forward to Summer to keep this normalcy going. I sure hope you get to go on your Anniversary trip, but I get it that you’d not want to worry about anything else getting there or planning just to cancel again. Enjoy your day.

        1. Yeah, I’m not worried about the new variant for safety’s sake, but I don’t want to be stuck in another country if they start instituting mandates or travel restrictions. I am already a nervous nellie about traveling overseas b/c I don’t have any experience with it, so it doesn’t hold much appeal to me at this point.

  3. You look great in all these photos. Makes me want to pack up and leave for a vacation. That is great you have another Florida trip to look forward to and how fun for Becca. I’ve been do Disneyworld once……1986, when my 1st baby was 6 months old. We stayed with friends who lived 2 hrs. away from Disneyworld. We had a great time. I live on the West coast, so we just haven’t gone back.

  4. I really do need to order the Away luggage that you recommend. What size do you have and has it held up well on air travel?

  5. I’m so excited for Becca and the marching band. What an awesome opportunity for them! Great outfit suggestions for us!

  6. Happy Monday JoLynne,

    Great post and I just wish Evereve would restore that wrap, it looks adorable! Would you mind telling what Goyard bag and size it is that you own?

  7. These outfits all look great. Since I have been to numerous beach weddings I do have one comment on that outfit – you will never be able to wear heels – albeit chunky ones – on the sand. Flat sandals are your only option. I think that dress would still work. I really can’t tell if that would make it too long, but the look would be great.

    Also, I love the 7FAM shorts. I am looking for a pair in white denim and might see if I can find that pair.

    Thanks for laying this all out for us.

    1. Yeah, I wondered about that. I wasn’t sure if all beach weddings were actually on sand or not, lol. But that’s good feedback, and I do think this dress would be cute with delicate gold or white flat sandals.

  8. I think my father in law is planning another family vacation to Florida this year and I am so excited for that! I ordered the blue top from Banana Republic, but I was down with a migraine when it came in and I haven’t really looked at it. I also jumped on the Vince Camuto wedges that I’ve been eyeing since I first saw you wear them. When I found them on sale, I knew it was meant to be! Lol! Your Becca (I go by Becca as well) is going to have a wonderful time on her band trip! My oldest just got home from a week at DisneyWorld with his high school band. They were invited to March in the Main Street Mardi Gras parade! Trip of a lifetime, for sure!

  9. Super cute! Love the blue and white dress. It would look cool with some of the chinoiserie jewelry I have been seeing around.

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