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20 Must-Have Vacation Dresses Inspired By Alex Drummond

She wore so many cute pieces on her tropical getaway! 🤩

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Vacation Dresses Inspired by Alex Drummond
Alex Drummond

Every item on this page was chosen by an editor from The Pioneer Woman. We may earn commission on some of the items you choose to buy.

If you’re planning a summer vacation what you’re packing should feel just as joyful as the getaway itself, and Alex Drummond knows exactly how to choose pieces that capture that feeling. In fact, her recent Cabo babymoon and anniversary trip delivered plenty of inspiration.

Throughout her trip, she wore so many cute pieces that captured the perfect vacation mood, from breezy swimsuit coverups to polished midi dresses that feel especially right for a resort setting. Alex’s outfits lean toward easy, feminine dresses with flowy silhouettes and soft prints that feel just as wearable for a date night at home as they do on vacation.

Any vacation styles should also move easily from daytime activities to dinner, with details that feel flattering, comfortable, and naturally photo-ready. Case in point: Alex recently wore a playful, tropical-print mini to a sunset cruise then dinner right after, proving just how useful a versatile vacation dress can be.

So, whether you’re adding to your suitcase or simply updating your warm-weather wardrobe, these vacation dresses inspired by Alex Drummond are a great place to start.

Get even more summer style inspo from Alex:

Alex wore this one while lounging by the pool—and it’s easy to see why! The sweeping diagonal stripes in peach, cream, and magenta give this dress a sun-drenched, retro mood, while the long, easy silhouette keeps it feeling relaxed and effortless.

With its scoop neckline, wide shoulder straps, and elegant full-length silhouette, Alex’s Amazon pick strikes a nice balance between polished and comfortable. The ruched detailing adds soft shape, while the side pockets give it practicality.

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Hello, bold florals! This mini has that carefree vacation energy that instantly puts you in a summer state of mind. The sleeveless tank shape is easy and relaxed, while the ruffle hem adds a feminine touch that makes it feel more styled than a basic throw-on dress.

Similar to an ocean-hued dress Alex wore recently, this bright blue number brings a fun, dressed-up twist to boho summer style. The asymmetrical neckline is instantly eye-catching, while the tiered details allow for soft movement.

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All the perfect makings of a warm-weather staple: spaghetti straps, easy A-line shape, and breezy boho feel. The relaxed silhouette will keep you comfortable, while the long, sweeping length gives it that romantic finish.

Grab this one for beach days that call for something light, pretty, and uncomplicated. With its airy A-line fit and delicate ruffle cap sleeves, it feels as sweet with flat sandals by day as it does dressed up for dinner later on.

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Summer stripes are so in! It also has spaghetti straps to give it a light, barely-there feel that’s perfect for hot days and a long, flowy silhouette which creates beautiful movement as you walk.

An embroidered palm tree print is beyond perfect for your vacation look. Short sleeves and functional buttons down the front add to its effortless appeal, and the detachable waist belt lets you define your shape in a flattering way.

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Resort wear at its finest, this pick is easy, breezy, and just a little flirty. The tie-shoulder straps add a darling detail while the flowing length, playful print, and cutout design give it a standout finish.

From boat rides to dinner, this tropical dress does it all. Seriously, that’s exactly what Alex wore it for! Its tiered silhouette gives it plenty of movement, while the belted waist adds shape and keeps the look flattering.

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Talk about effortless elegance! The espresso tone gives it a warm, sophisticated mood, while the square neckline and tie-close straps add a soft, feminine structure. It also has functional pockets.

Alex used this sweet number as a swimsuit coverup, but it can also be dressed up for evening plans. It has carefree, throw-on charm with cotton fabric that keeps it feeling light and breathable. You’ll also love the floaty silhouette with ruffle trim and button details.

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This pick feels straight out of a tropical postcard. The halter neckline frames the shoulders beautifully, while the backless detail gives it a bold, breezy finish that feels made for sunlight and a little spontaneity.

Made for those golden hour moments when you want something easy but still eye-catching, its tropical print brings plenty of personality, while the maxi length adds that easy, sweeping elegance that always works in warm weather.

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There’s something inherently nostalgic about eyelet! Add the embroidered pattern to a lovely, flutter-sleeve mini and the result is a dress that feels airy, sunlit, and endlessly appealing.

Bright florals contrast so beautifully against a black hue. Other features include lantern sleeves for bold movement, a v-neckline to keep things balanced and flattering, and a tie-back detail for added intrigue.

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The coastal feel of this outfit makes it especially easy to love. The soft blue base with red and white vertical stripes gives it a slightly vintage look, while the loose, flowing silhouette keeps it plenty breathable. Bonus: those adorable ruffled straps!

Take this one to the beach then continue wearing it the rest of the summer, too. The scalloped straps and neckline give it a delicate, almost handcrafted vibe, while the floral pattern brings softness. The fitted waist adds definition, and the fuller skirt with its tiered hem is both polished and easy.

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Just look at that on-vacation energy that a bold blue always delivers. The wrap-style silhouette is flattering and easy, creating soft shape through the waist while keeping the overall look relaxed and wearable.

Designed with a relaxed tank silhouette and a flouncy ruffle hem, this one is ready to make its home in your suitcase. Pull it out and pair it with sandals and simple accessories for an instantly summery look.

Headshot of Macie Reynolds
Macie Reynolds
Assistant Editor

Macie Reynolds is the assistant editor of E-Commerce and SEO for The Pioneer Woman.

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