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Unless otherwise specified, all sizes in this post are listed in women's.
1. A tie-bodice strappy midi dress, because you deserve to kick off your vacation planning with the wardrobe equivalent of those fancy welcome drinks you get when you check into a resort. With a cute lil’ keyhole in front and some fun flounces at the hem, this dress is as refreshing to look at as it is easy to wear.
2. A lightweight camp shirt that’s as effortlessly cool as a poolside breeze. It’s light. It’s drapey. It goes with everything. And, most important of all, it’s perfectly packable. Yes, vacation styling can be that easy!
Promising review: “These camp shirts are becoming a spring/summer staple for me. I love the soft fabric and the fact that they are cool, but opaque enough that they don't show your bra underneath (even white). The gathered yoke and shoulder make them drape beautifully, and they skim over my mom's belly without clinging or gaping at the buttons. The length is perfect to leave untucked. They do need to be line-dried and ironed to avoid ruining the viscose fabric, but it's a worthwhile trade-off to me for such a versatile shirt. I've worn them with both pants/shorts and long skirts for church.” —indigosand
Price: $19.98 (available in sizes XS–XXXL and six colors)
3. Some cropped barrel-leg carpenter jeans, if you’re looking for a fun way to vacation-ify your usual denim. With a comfy, relaxed fit and an effortlessly cool white colorway, they’re so much more vacay-ready than a regular ol’ pair of jeans. What better time to elevate your casual wardrobe staples than while you’re out of the office?
4. Or, some cotton canvas-linen blend cargo pants, if your dream vacation warrants ditching the denim altogether (I love jeans as much as the next person, but sometimes they are just TOO DANG HOT). These trousers are super easy to wear, thanks to the relaxed fit — and, I mean, don’t knock cargos. Cargos are great. Yes, I will die on this hill.
Promising review: “Good fit, really nice fabric. Looks expensive! These are really nice pants. I wear an 18, and they fit true to size. Spot on. These are a nice length and look good with a sandal or a shoe. The fabric is a linen cotton and feels really nice. This looks like a much more expensive pant. I bought the matching jacket as well.” —Lil
Price: $28 (available in sizes 0–26 Plus and three colors)
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5. A sporty yet sweet belt bag you just KNOW will take you and all your essentials anywhere you want to go. Whether you wear it as intended or sling it crossbody, this handy pastel pick packs tons of space for your on-the-go vacay must-haves.
6. A smocked cotton tank with an eye-catching peplum hemline you’ll see yourself wearing everywhere from the beach to the bar (or even to the beach bar!). Ugh. Perfect. Just go ahead and pin it, already.
7. Some drawstring utility shorts, if the kind of vacation you’re envisioning relies heavily on transforming yourself into Indiana Jones or Lara Croft. Ideal for adventuring, these paper bag–style shorts are also super cute, thanks to their adorable patch pockets.
Promising review: “Summer staple! These are so cute. They have a paperbag elastic waist with a drawstring. I wear a size 14, but I didn't want them to fit tight, so I got an XL. They are very roomy. I'm going to go and try a large one, and I'll let you know... but these are keepers either way. Good length. Cute design.” —lisa
Price: $16 (originally $22.98; available in sizes XS–XXXL and four colors)
8. A pair of fun beaded slide sandals, because, I mean, why the heck not? If ever there was a time for whimsical footwear, vacation is IT. Your I’m-outta-here mood board won’t know what hit it.
Promising review: “GET THEM! These slides are ADORABLE and super comfortable. The footbed is padded, which makes them comfy to walk in all day. The beaded sardines on top are very well made! I love these sandals, and I get compliments on them every time I wear them. They are TTS. I'm usually an 8.5, but I had to get the 9, and they fit fine. There's a little bit of space in the back of the foot, but not too much.” —Finnfor3
Price: $24.98 (available in sizes 6–11 and four designs)
9. A split-neck cotton midi dress that’s as easy and breezy as a tropical getaway. With a smocked waist, tiered skirt, and tons of fun patterns and colorways to choose from, this Nanette Lepore pick will have you dreaming up so many ways to style it. Perfect travel dress? Perfect travel dress.
Promising review: “Great quality, fun summer dress! This dress is of such high quality and a great, comfortable fit. The patterns were so cute that I ordered three different ones! If by chance you are really debating between sizes, size down.” —Alison
Price: $12.96 (originally $28+; available in sizes XS–XXXL and eight patterns)
10. A floppy, wide-brimmed hat, so you can stay cool in more ways than one. Is your trip-planning collage full of photos that evoke Sailing The Seven Seas In Style or Motoring Around The English Countryside In Fabulous Fashion? This is the way to do that. Even better, it's adjustable, so it’ll adapt to fit most noggins.
Promising review: “Perfect floppy hat for travel or the pool! Large floppy hat, perfect for the beach, and keeps the sun out of your eyes. I bought the hat to decorate and wear to my company's Kentucky Derby office party. Folds easily for packing, but I think it could be reshaped. Good value.” —Stacy
Price: $9.97 (available in two colors)
11. A flippy ruffled mini skort, because, I mean, it’s vacation time. That means it’s also time to let your gams live a little — and this flirty (and, uh, secure, because that's the beauty of a skort) little number is perfect for that. Just don’t forget the sunblock!
Promising review: “This skort is adorable! It comes a little wrinkled, so you have to wash it like hanging it before you wear it, but it has built-in shorts and fits true to size! I'm 5 feet one and 145 pounds, and a medium fits great! This is going to be great for summer, I got the white and the pink, and they're both so cute.” —Megan
Price: $5.29+ (originally $14.98; available in sizes XXS–XXL and two colors)
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12. A cheerful beach tote that’s cute enough to use as, y’know, a regular day tote, too. Waterproof and sand-proof, it’s roomy enough to pack your day-at-the-beach essentials without being overwhelming. Also, it comes in SO. MANY. COLORS. So many! No matter what color palette fuels your travel inspiration mood board, there’s definitely one here that’ll complement perfectly.
Promising review: “Perfect purchase! Exactly what I needed!! Such a super cute, perfect find! This bag is exactly what I needed! I really wanted a pretty large-sized bag, easy to clean and locate items within it, durable, cute, and fairly priced! This bag checked off all the boxes on my checklist and then some! I always seem to be on the go and really like to be prepared, making sure I have everything I need or may need (and also what my son and husband may need). As a nurse and a mom, I am always thinking about the 'what-ifs' and 'just-in-case' scenarios, and this extra-large, lightweight bag offers me a little extra peace of mind since I can fit so many items in it! This bag is especially great for day trips, boat or beach trips, shopping, and so much more! I love how this bag is different from any and all of my other bags and am super elated that I purchased it!” —KaraM
Price: $19.88 (available in six colors)
13. An eyelet midi skirt you’ll daydream about wearing while wandering around secret gardens or elegant castles. Pull-on styling means it ticks all the practical boxes for a vacation wardrobe piece — but with that tiered eyelet hem? So dreamy! So romantic! So wonderfully Instagrammable!
14. A flounce-sleeve tee for those days when you want the ease of a T-shirt with a little extra impact. Sensible enough for any wild adventures you might get up to while you’re away, but with enough oomph from its floaty, lace-inset sleeves to bring some Capital-F Fashion to your ensemble, it might just be the ideal vacation tee.
Promising review: “Lovely top! This top is so cute. As another reviewer said, it looks much more expensive than it is. I purchased the top in both red and navy and love both. The top is very comfortable and fits true to size. Great purchase!!” —Pamela
Price: $14.98 (available in sizes XS–XXXL and three colors)
15. And a bouncy swing dress that wears like a tee, but looks so much more put-together — and let’s face it: Part of the joy of figuring out a vacation wardrobe is balancing the scale between the easy-to-wear and fun-to-wear sides. Can’t you just see yourself pairing this pick with some white sneakers for a day exploring cobbled alleyways or bustling street markets? Or adding some pretty sandals to it and dining by the ocean? Or…well, you get the idea.
Promising review: “Beautiful dress. The pink color is the perfect shade. The fabric is soft and, because it is cotton, comfortable in warm weather. Hem length on me is below the knee. The perfect spring and summer dress. Also love the neck. I can wear different necklaces to keep it casual or dress it up. Perfect.” —Karen
Price: $12 (originally $16.98; available in sizes XS–4X and four colors)
16. Some mirrored pink aviators to protect your peepers and add a dose of playfulness to any vacation-friendly 'fit. No uncomfortable squinting for you as you soak in the sun!
Promising review: “The perfect mirrored pink sunglasses! I'm really happy with this purchase from Foster Grant. Reviews complained that these sunglasses felt huge. However, these aviators fit my face like a PERFECT FIT! These are actually my first mirrored lenses, and I'm in love with these pink shades!” —RetailLover
Price: $14.97
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17. A smocked cotton mini dress, in the event that your idea of a perfect vacation involves embracing your best cottagecore life. The puffed sleeves and smocked bodice of this piece will be right at home in that darling countryside rental cottage you’ve been eyeing (and all the idealized versions of it you’ve been busily pinning to your planning board).
18. A clean white slip-on sneaker, because they’re the ultimate goes-with-everything vacation wardrobe staple. These canvas slip-ons might be simple, but they’re anything but basic — and with memory foam insoles, you can also be sure they’ll keep your feet nice and cushy on any and all vacation escapades you might have in mind.
Promising review: “I love everything about these shoes. Unexpected quality for the price point. They are the perfect summer slip-on shoe that goes with just about everything. I would recommend spraying with a protectant. They are comfortable, and one pair easily lasts the season. There's a nice cushioned insole that makes these comfortable to wear all day on the go. I've worn them on vacation, and because they're so versatile, I find I don't need as many shoes. By far my favorite summer shoe.” —Sara
Price: $19.98 (available in sizes 6–11; also available in two additional colors)
19. A pair of linen-blend shorts with pineapple (pineapple!) embroidered embellishments, so you can stay comfy and stylish, no matter how hot the climate you’re headed to may be. Nothing beats linen for warm-weather escapes; even better if you can elevate it with unexpected details, right?
20. A smocked romper with vintage charm that’ll bring to mind soda shop afternoons and evenings on the dance floor. How could it not, with that polka-dot pattern and those super fun flounces?
21. A silky little scarf that’ll look just darling keeping your hair out of your face — or tied around your neck, or hanging from your favorite bag, or… well, anywhere else you want to put it. You can be anyone you want to be on vacation. Why not become the kind of person who can absolutely, 100% pull off scarves like this one? There’s a reason you added all those photos of Audrey Hepburn in Roman Holiday to your inspo board, after all, right?
22. An embroidered midi skirt made for soaking in the sun. Adorned with a sunny palm tree and other tropical details, this drop-waist pick will fit right in at the beach hut.
Promising review: “Beautiful summer-themed skirt! This skirt (and matching top) is beautiful. The embroidery is top-notch and looks so high-end. No one would suspect it came from Walmart. Love that it has pockets. The length is great, I'm only 5 feet tall, and it's not too long. Hits mid-calf on me.” —Jan
Price: $32 (available in sizes XS–4X)
23. A sunny little clutch wallet, because what better way to celebrate being on holiday than by gifting yourself something cute to keep your most important stuff in? You’ve got plenty of nights on the town ahead of you, so pack up this cheerful yellow pick with your ID, your cards, and your cash, and get ready to have some fun.
Promising review: “Grab the yellow one before it's gone! I snagged the yellow wallet to match the smaller yellow shoulder bag. They are a lovely set. The wallet feels so smooth. Enough room for the essential cards, cash, and coins. It fits upwards, not horizontally, in the smaller tote bag. Will be used a lot in spring and summer. Love a pop of color with the yellow. Thanks, Walmart.” —Shashashi
Price: $14.06 (also available in three additional colors)
24. Some mesh Mary Jane espadrilles that are basically the ideal vacation shoe. These beauties combine the breathability of classic espadrilles with the benefits of a sneaker, all in a Mary Jane-style silhouette that’ll suit casual day looks and fancier nighttime ones alike. Style away!
Promising review: “Perfect summer shoe! Such cute and on-trend shoes! Bought last year’s version, and they were the perfect summer shoe, and I could walk forever in them when on a trip in Italy. Memory foam is really great! This year’s version with the mesh is so stylish. Don’t sleep on these!” —Kristine
Price: $19.70+ (originally $44; available in sizes 6–11 and six colors)
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25. A puff-sleeve beaded cardigan, because the nights can get chilly when you’re traipsing ‘round the world. Throw it on top off whatever else you’ve got going on, and bam — it’s a ~lewk~ without you even needing to try.
26. Or a classic cropped denim jacket, if you anticipate your day-to-night temperature changes being a little more variable. Bonus: It looks just as cute tied around your waist as it does when it's actually worn — meaning you’ll never have to worry about accidentally leaving it somewhere.
Promising review: “Perfect denim jacket to dress up an outfit! Excellent quality denim jacket. It’s super cute and hits at the perfect place. I’m really picky with quality, and I’ve been on the hunt for a darker wash denim jacket, and this checks all my boxes! Perfect for dressing up leggings and a tank top, or for layering over a dress. I’m constantly impressed with Free Assembly.” —Rachel
Price: $32 (XS–XXL)
27. A knit sleeveless graphic top as bright as a Popsicle, because what’s more fun that coordinating your vacation wardrobe with your favorite poolside treat? Bold and playful, it’s as fun to wear as it is easy to pop on.
28. A crochet beach cover-up that, honestly, even works as an open-work top if you pop it on over a cami instead of a swimsuit. It’s an easy way to add some eye-catching texture to any I'm-definitely-not-home-right-now look.
Heads up that the matching shorts are sold separately.
Promising review: “It is so cute and comfy. It is so beautiful, perfect for the beach or outside in front of your pool. It's so cute.” —Kar
Price: $12.98 (available in sizes XXS–XXL and two colors)
29. Some tailored linen blend shorts, because they’re truly the epitome of resort wear. Structured yet still relaxed, they’re just packed with the kind of casual cool you’ve been hoping to exude when you roll up for dinner at the dockside grill. Right? Right.
Promising review: “Awesome find! This makes the fourth pair of these shorts I've purchased. They're true to size and color, and the fabric is lightweight without being see-through. They travel well and do laundry well. Very happy with this purchase. Wish they had more colors. Length is perfect, too. Great value.” —Boni
Price: $14 (originally $19.98; available in sizes XS–XXXL and six colors)
30. And lastly, some playful parrot earrings that’ll make a statement whether you’re actually on holiday right this very second, or just in the dreaming-about-it phase. Time to bring Polly home to the tropical landscape from whence she came!
Promising review: “Whimsical and unique! Gorgeous craftsmanship and beading. They are very delicate and can bend, so I would be careful with these because they're made on a felt backing, but the beading is gorgeous, and they're so unique.” —Jessica
Price: $8.92 (also available in eight additional designs)
Still looking for the perfect wardrobe update for *y-o-u*? Try these:
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* Just 31 Going Out Clothing Pieces That You Won’t Want To Peel Off The Moment You Put 'Em On
* Backless Tops And Dresses For Those Who Prefer Business In The Front And A Party In The Back
Plus, activewear, and finds from Amazon, Free People, Gap, Nordstrom, Old Navy, Torrid, and Walmart.
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Reviews for this post have been edited for length and/or clarity.
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