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Alex John Beck

You've chosen a locale and booked your ticket, but between now and paradise is the packing process. Dressing for fun in the sun? That's easy enough. But when you factor in outfits for an al fresco dinner, a stroll through the city center, and a drink (or two) at the local bar, things become a little more overwhelming.

Your options: Sit there indecisively overlooking a mound of clothes, or follow this vacation style guide (packed with on-trend pieces curated by Macy's The Edit) and thrive at the beach, pool, or wherever else you end up. Plus, you'll have plenty of quality Instagram vacation content.

What to Wear: To the Beach

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Alex John Beck

While a bathing suit is typically an essential part of any beach ensemble, you can leave the bikini at home if you're not planning to lay out or swim. Instead, let your accessories steal the spotlight. A lightweight hat adds instant impact to any look, while protecting you from UV rays. Pair the oversize brim with a body-hugging crop top and a high-waisted midi-skirt for a look that'll make you stand out in sea of swimsuit sameness.

What to Wear: For a Pool Party

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Alex John Beck

Cover-ups are child’s play. To make a real splash, pair a printed one-piece with high-waisted trousers that crop just at the ankle. You won’t be swimming in sweat so long as you keep it airy with lightweight white pants (these come with a Hamptons-friendly feel). Just don’t forget a structured wicker bag, the unofficial token of a fashion-forward vacay.

What to Wear: To the Market

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Alex John Beck

Whether you're shopping in the city or visiting a small, local market, you want to be practical, comfortable, and appropriately chic. A sleeved maxi dress is as utilitarian as they come. That said, it’s not your style to blend in too much. Opt for a tie-dye iteration in a vibrant hue for an eye-catching ensemble. Pair it with leather strapped sandals, and let yourself wander from your travel companions. Don't worry; they’ll find you.

What to Wear: To Get Cocktails

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Alex John Beck

The nighttime look can get quite complicated, but you’re on vacation—leave any wardrobe worries at home and keep it simple with a silky wrap dress. It’s equal parts sexy and sophisticated, and most importantly, it’s easy and barely takes up any luggage space. Dress it down with comfortable sneakers or up with dainty jewelry and wrap-around sandals.

What to Wear: For the 'Gram

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Alex John Beck

If it wasn't posted on Instagram, did your vacation even happen? Sure, a new experience and fresh surroundings may call for a digital detox, but first, a really great outfit must be shared.

Boost likes with a sophisticated, floral-print set. A sliver of exposed skin between a bustier-style crop top and its matching high-waisted body-con skirt provides a subtle allure, especially when worn in front of the prerequisite white wall or infinity pool. Angular sunglasses and an oversize hat complete the picture.

What to Wear: Out to Dinner

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Alex John Beck

There are two very specific instances where a white dress really shines: on your wedding day, and on vacation. The color exudes a carefree, fresh feel that complements just about any scenic locale, whether it be a Mediterranean backdrop, the deck of a yacht, or a candlelit dinner.

The trick to bringing this very simple piece to life lives in textures: Fringe trim, knit patterns, sheer layers, or, ideally, some sort of combo elevate the look without losing its effortless vibe. Wear it with color-blocked sandals—and a sun-kissed glow—for a minimalist but powerful effect.


Styling by Tenille Yamashita, Hair by Rolando Beauchamp, Makeup by Kristi Matamoros, Props by Todd Wiggins