7 Vacation Outfits for Every Type of Destination

Fusalp Oria Down Ski Jacket

Perfect Moment JG Bib Ski Pants

Aztech Mountain Ajax Half-Zip Sweater

Miu Miu Wool-Cashmere Balaclava

The Tropical Escape

If you are headed for a warm weather destination this season, be sure to pack something bright to complement the tropical foliage. This matching set from Alémais is perfect for day-to-night outfitting, should you find yourself sipping caipirinhas in Rio de Janeiro or going off the grid on the North Shore. When it comes to accessorizing, play up the whimsical, scarf print with a bold, beaded necklace (we love this one from Lié Studio) and keep your other accessories simple. A luxe raffia bag and minimalist flat sandals will go a long way in the styling department.

Alémais Flores Silk Scarf Top

Alémais Flores Sarong Skirt

Lié Studio The Mary Agate Sterling Silver Necklace

The Cabin Upstate

Cozy, cabin weekends call for easy pieces that have a laid-back, yet elevated vibe. A Fair Isle knit immediately adds a sophisticated layer to a blue jean ensemble (this one from Veronica Beard is an alpaca-wool blend, so you know it’s going to keep you warm too). A relaxed pair of fitted jeans (we love Khaite’s Abigail), should be worn to match your vacation mood. Add punchy ribbed socks to pair with shearling-lined boots for outdoor strolls or to snuggle up by the fire.

Veronica Beard Anne Fair Isle Sweater

Khaite Abigail Stretch Jeans

Comme Si The Merino Tube Sock

Sorel Tivoli V Waterproof Boot

The Big City

No matter what city you’re headed to, whether that be in Vienna before skiing in the Alps, or Tokyo for sake, sushi, and shopping— an urban-appropriate outfit is always a must. A shearling jacket goes a long way when traveling, in terms of warmth and versatility, and we love how classic this Banana Republic aviator style is. Pair it with a cozy sweater (cashmere from The Row is always a good idea), sleek trouser pants, and kitten-heeled boots that you can actually walk in. It’ll take you from a long day of museum hopping straight to your dinner reservation with ease.

Banana Republic Shearling Aviator Jacket

Almina Concept Adjustable Waist Trousers

Toteme The Mid Heel Bootie

The Beach Getaway

Planning to lounge in St. Barths or take in the ocean views in Tulum? Pack something easy and breezy that will take you straight from the beach to sunset cocktails. Agua by Agua Bendita’s dreamy one-piece has a romantic feel that will set you apart in a sea of black bikinis, and for a modern take on resortwear, top it off with Jade Swim’s sheer pant set. It’s a contemporary, yet refined take on coverup dressing that gives off the carefree attitude you want to embody while on holiday. A minimal leather sandal is the only accessory you need (besides a roomy beach bag, of course).

Agua by Agua Bendita Ébano Bougainvillea 17592

Jade Swim Amaya Wide-Leg Pants

The Wellness Retreat

If you’re gearing up for a series of sun salutations at a yoga retreat in Sedona or have a wellness-packed weekend planned at Amangiri, your style should reflect the harmony you’re hoping to achieve. Stick with an earth-toned color palette, like this zen green set from Lululemon. A comfy pullover is useful for post-practice tea or unwinding after breath work and meditation sessions, while a designer sneaker (such as this one from Loewe) will get you to-and-from every activity on your itinerary with ease.

Varley Vine Half Zip Pullover

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Lululemon Flow Y Nulu Bra

Lululemon Align™ High-Rise Pant 28″

The Wine Country Tour

If you have a girls’ trip lined up to Napa Valley, channel the laid-back feel of the California coast by packing casual wardrobe staples that never go out of style. A cable-knit cardigan atop a flouncy, plaid blouse (Dôen excels in this category) feels like the modern way to do Western style. Tuck it into dark denim jeans and add walkable, leather ankle boots for a long day of touring the vineyards and horseback riding (you could also swap them for flat, suede booties here as well). This is what a California winery look should be all about—cool and comfortable.

Madewell Low-Slung Baggy Jeans

Loeffler Randall Ginny Square Toe Ankle Boots

Kristina Rutkowski is a New York-based writer and editor with over 15 years in the fashion industry. Previously the Senior Fashion Market Editor at InStyle magazine, she covered all things trend and shopping related. She has also worked in the fashion departments at both Self and Glamour. Her byline has appeared on HarpersBazaar.com, Vogue.com, WSJ.com, VanityFair.com, WWD.com, TheZoeReport.com and more. Find her on Instagram at .