These 12 Vacation Outfit Ideas Are Universal Crowd-Pleasers

If it were up to us, we'd choose to wear vacation attire all year round. Long, billowing dresses; tropical-inspired accessories; and sheer cover-ups all beat work-friendly trousers any day. Unfortunately, for those of us not living near the equator, reality (and a general sense of public decency—no one wants to see our bikini straps showing at dinner) means our holiday outfits are typically tucked away until our next vacation.

Alas, the season of getaways is finally here and so is our renewed excitement over the looks we're dreaming up. The vacation aesthetic is one that seems to be universally shared: floral-printed button-down shirts, wide-brim hats, any kind of strappy footwear that doesn't require a sock. In honor of summer's kickoff, we've gone ahead and found 12 looks that are undeniable vacation hits. So take note and pack up these ensembles the next time you're loading up that suitcase.

Look 1

Whose ideal vacation vignette doesn't include long summer nights while you lounge around in a dreamy, white, gauzy gown? This look is the poster child for the archetypal vacation look. Once you find the perfect dress, toss on a straw hat that would bring Audrey Hepburn to her knees and add a pair of simple, low-heeled sandals. 

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Look 2

While Lisa wears an eye-catching Dries Van Noten top, we recommend scouring your local men's vintage section for a similar, more affordable floral button-down. It'll also help you achieve an oversize fit. She keeps things cool and casual in a pair of linen Bermuda shorts and a set of matching Chanel accessories we can only dream of adding to our wardrobes. We'll settle for what we can get our hands on in the meantime. 

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Look 3

Looks like bandana tops aren't just coming for your swimsuits. You can easily achieve a similar top by folding, rolling, and tying a silk scarf or bandana that you have lying around at home. But you can also go the lazy route by buying a premade handkerchief top. Re-create this look with a fun-colored bias skirt, some beach-ready slides, and a set of statement sunglasses.

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Look 4

If wanting an entire closet full of wide-brimmed straw hats is wrong, I don't want to be right. This minidress look instantly goes from night on the town to vacation getup with a simple boater hat. Just grab your favorite puffy-sleeved LBD and mules and don't think twice about picking up the next straw hat you find. 

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Look 5

Who knew we'd be looking to classic '90s boy band music video attire for vacation packing inspiration, but here we are. It's 2019, and all we want to wear is a sheer, all-white getup (and another straw hat, of course).

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Look 6

This look is low-effort but somehow nails the exact aesthetic we're trying to achieve this season. And how we ever missed these diamanté bike shorts, we'll never know. We're making up for it by packing them in our suitcases the next time around. Finish off the look with one of your own cozy oversize tees and a classic pair of Birkenstocks. Comfort is key, after all. 

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Look 7

Meet the outfit you pre-plan weeks in advance in hopes of getting the perfect vacay Instagram shot. A matching mini two-piece set grounds the look, so feel free to go as extra as possible with your accessories. We're taking notes from Nicolette and packing an over-the-top fringed straw bag and a pair of strappy lace-up heels. 

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Look 8

We've had this Sleeper gown on our vacation packing list for some time now. It fits in just as well at a beachside bar as it does in the English countryside. We're looking to Blanca for styling notes on how to make this dress work for a port of call. She's maximizing her use of prints by dressing up the floral pajama-like dress with a plaid bucket hat and tortoiseshell slides. The resulting look just goes to show that mixing prints is a new task we should embrace. 

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Look 9

This simple top-and-jean ensemble is exactly what we're copying for our next getaway. Brittany brings the city to the jungle with a pair of baggy jeans but maintains a bright color palette that's a perfect fit for the lush environment.

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Look 10

Mark this as an outfit we never would have thought up on our own. A cow-print skirt, a bright-yellow button-down, a straw hat… We're hoping to re-create this look piece by piece.

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Look 11

If only our middle-school selves could see the way we've since glowed up the trends of the past. From the tie-dye skirt to a tie-front top to stacked anklets, this look achieves the same nonchalant cool we were gunning for at 13. Now that we're older, wiser, and can get our hands on chicer iterations of the same early aughts trends, maybe we can finally pull it off, too. 

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Look 12

We're going to need Staud to release this zebra cover-up set ASAP. Ever since coming across this look, I've been bookmarking every semi-sheer zebra-print piece of clothing I've come across in hopes of re-creating a similar outfit. Staud's designer, Sarah Staudinger, rounds out the look with a pair of her own padded flip-flops (also a must-have) and a shoulder bag. 

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Up next: 21 pretty dresses I'm buying because of our readers.

Contributing Editor

Ray Lowe is a contributing editor for Who What Wear. She's spent the last decade living in New York, but now that she professionally works from home, she's slowly been going back to her roots by splitting time between NYC and L.A. A year ago, she left a four-year stint as a fashion editor for Refinery29 to explore the freelance life. Nowadays, she does just about everything from penning online articles (for Who What Wear, Refinery29, Elle, Cosmo, and many more) to writing scripts, styling, and finding ways to fuse her love for both Disney and fashion. Her main beat is fashion (trends, emerging brands, affordable finds, you name it), but you may find her dropping in with a beauty story every now and then. As for her personal style, she'd best describe it as a balanced blend of basics and contemporary trends, often with a dash of Mickey Mouse thrown in for good measure. In her spare time, she can be found coddling my pets (a French bulldog and a rescue cat), curating travel itineraries for her friends, scrolling through Instagram for up-and-coming brands, and watching so-bad-they're-good films.