What to Wear on Vacation, For Every Type of Weather

Year-round vacation looks should always include a peasant dress, which is breezy and a lightweight, packable item but can also be layered for chillier travel destinations. Opt for a long-sleeved version that can be styled with a cinched waist, like the Lemlem Peasant Dress ($425) in its top-performing medallion print, and coordinate with sandals or sneakers for a more adventurous day.

This Mara Hoffman Alora Dress ($425) could easily be dressed up with a pair of heels for a night out, but with flat sandals, it's still casual enough for the beach.

It's never a bad idea to source one of these pieces with matching pants, like this COS Striped Midi Wrap Dress ($150). Wear this design cinched at the waist with sandals, or layer it over the straight-leg satin pants and style it open and breathable.

The Mikoh Maracas Dress ($212) comes in five distinct neutral shades, with night, bone, chalk, and cafe as alternative options to this bermuda colorway. Because it's so minimal in form, you can accessorize it with your favorite statement jewelry or a big straw hat.

While a classic pair of jeans may be a staple, printed pants offer a chance to switch things up. These Lisa Says Gah Robyn Jeans ($188) are vintage inspired and top-rated on the site. Make the pants the focus, keeping the rest of your outfit more pared down, or go full-blown maximalist and coordinate the rest of the ensemble with the pants.

Sport these EM on Holiday Kokomo Pants ($157) with a white T-shirt to draw focus to the Happy Hawaii print, plus a fun-colored shoe that's easy to walk in. They'll also perfectly complement a denim jacket on a breezier day.

These H&M '90s Flare Low Jeans ($21, originally $40) are made from a thick denim, so they'll help keep you warm if you're in need of extra layers. When the sun's out, you can style them with a cropped baby tee and a pair of aviators.

PatBO sales director Ashley Rahman names a robe as the brand's travel staple, since it can be worn as a cover-up or layered over jeans and a tank top. The PatBO Violet Tie Front Robe ($270, originally $450) is semisheer and comes with a functional sash.

This Zara Muslin Kaftan ($70) will go with everything in your wardrobe and has drawstrings at the chest, but side slits for ventilation at the hem.

The Andrea Iyamah Sarina Robe ($147, originally $210) comes in a unique harvest lemon print and has exaggerated ruffled sleeves that lend regal flair. Bring a pair of oversize statement earrings to play up the resort vibe.

Cutouts are continuously a major style trend. The Kadimah Kehlani Cutout Dress ($195) has been spotted on Alicia Keys and Gabrielle Union. Its viscose crinkle crepe fabric has a sensual feel, so you can dress it up with sandals and minimal jewelry to draw focus to the midsection, where a bamboo ring is positioned front and center.

The PatBO Riviera Plunge Cutout Dress ($477, originally $795) is a signature silhouette of the label, known as its bestselling hybrid dress that comes complete with a built-in bodysuit. This throw-on-and-go look is perfect for vacation — a simple beach dress to wear when sunbathing isn't a concern, and a complement to heels and go-to jewelry on a night out.

The Solid & Striped Lisa Dress ($298) is a versatile piece that is great for packing in your suitcase, because it can be repurposed more than once during your trip — perhaps with a light jacket and heels first, then barefoot at the beach.

Like a tunic, the bib dress is free-flowing and short, made for comfort and ease in the heat. Lemlem reports its Palm Leaf Bib Dress ($325) as a customer favorite because it's ultraflattering, designed to show off your shoulders and legs, and functional. Team it with a pair of neutral lace-up sandals and a woven bag.

This Mango Striped Ruffle Dress ($50) has a similar feel in a simple cotton fabric that can be worn over a swimsuit or under a jacket with heels for an event.

The Show Me Your Mumu Paula Pullover ($154) also comes in black, latte, citrine, and hot pink crochet, and while you may think it's made for swimwear only, if you find the right shapewear to wear underneath it, you can easily sport it with wedges and a clutch for dinner.

This Show Me Your Mumu Black One-Piece ($148) is part of the label's Scrunch collection, which became a big hit last year. Completed with thick, sturdy straps in a fabric that's 82 percent nylon and 18 percent elastane, the piece is flattering and also available in ivory, hot pink, sky blue, and watermelon-mint, a fun two-tone option.

The EM on Holiday Easy Living One-Piece ($96) is a fun option because the graphic slogan even makes a great foundation for jeans and Vans.

Solid & Striped's Landman names a pareo as the one staple item every traveler should own. This year in particular, we're seeing many three-piece sets available so shoppers can achieve a stylized, monochrome outfit. The Solid & Striped Pareo ($98) can be worn witih the matching Solid & Striped Sienna Top ($138) and Solid & Striped Sienna Bottom ($108).

This Tory Burch Printed Pareo ($189, originally $248) comes with tassels and beads and can be wrapped around the waist, or draped over the shoulder. You can also fashion it into a loose top or bandeau.

This Zimmermann Fringe Cotton Pareo ($235) teams nicely with a minimalist-colored suit, such as a sunshine-yellow or red.

Travel brands like Frankies Bikinis, EM on Holiday, Duvin, and Tombolo Company have become known for full cabana sets that are comfortable enough for the plane, the beach, and everywhere in between. Buttoned up and styled with sneakers for a day of sightseeing or worn as separates, coordinated with a swimsuit, these sets are a safe bet and simple in that you don't have to think up quite as many outfits while you're traveling. Team up the Frankies Bikinis Cheri Terry Cardigan Sweater ($98, originally $140) with the Frankies Bikinis Marty Terry Swim Skirt Bikini Bottom ($67, originally $95).

Tombolo Company is constantly releasing new, inventive embroidery on its terry-cloth sets. The Tombolo Gusanito Cabana Shirt ($138) and Tombolo Gusanito Cabana Shorts ($108) are inspired by two-piece ensembles from the '50s and '60s, embroidered with tequila bottles and agave plants.

You can choose whether you wear this EM on Holiday Pyjama Check Short Set ($157) to bed, to the beach, or with a pair of sneakers. The airbrush check print is also sweet enough to dress up with a strappy stiletto and fun minibag for a night out. Made from cotton poplin, each piece is screen printed by hand, which means your exact shade will be slightly unique from shoppers before you.

When it comes to vacation accessories, you need not check the weather app. Hat-wise, you should always look for something unstructured that you can fit in your suitcase. That way, you won't worry about crushing it when you're squeezing in other essentials. The EM on Holiday Thin Stripe Sun Hat ($52) has a contrast inner rim and adjustable rope pulley.

If you're headed to a destination that's slightly cooler, opt for this Sabaa Goods Haze Bucket Hat ($45), which comes in a faux-fur fabric that will keep your ears warm.

This ethereal Stone Road Baseball Hat ($35) has adorable nature graphics to keep you happy — and it makes for the perfect travel cap to wear on the plane, both on the way there and on the way home.

The Lack of Color Inca Bucket Hat ($149) is natural looking and can be coordinated with any outfit. Add a pair of gold hoops for simple accessorizing.

This Zara Pack of Chain Necklaces ($23) is ideal, because you can wear all three pieces together or style them separately, achieving a slightly different look on every day of your vacation.

The Roxanne Assoulin Cherry Bomb Bracelet ($80-$420) is bold and best worn as a stack with a simple white tee and denim. The beads on their own are striking enough to get noticed and incredibly easy to take off and put on.

Before you leave the house and set off on your travels, remember to clasp on this Chloé Alphabet Gold-Tone and Enamel Necklace ($450). It's an easy statement piece to work with everything from a colorful swimsuit to a ribbed tank top and jeans. Plus, it helps you define who you are while you're on-the-go.