Winter Vacation Outfit Ideas, Based On Your Destination

There are few things more wonderful than setting your OOO notification and keeping your laptop fully shut as you take a much-needed vacation. And although many typically plan a trip in the summer, there’s also something to be said for winter getaways. The months can be quite dull, so might as well escape for a bit, right? Should you be heading out of town in the coming weeks, packing is likely on your mind. Or, to be more specific, packing your outfits. Whether you’re jetting off to a tropical island or staying nearby in a quaint countryside town, stepping out in chic, feel-good looks is a must.

For Lesleigh Jermanus, the founder of Alémais, a midi or maxi dress in a coastal print is always on her packing list for a warm-weather location. Of course, swimwear is essential as well. “You’ll always be prepared for a spontaneous cold plunge or hot tub; I love a high contrast suit, something patterned that speaks to elements of the ocean,” Jermanus tells TZR. On the opposite end of the spectrum? “If you're heading to a ski town or a chilly winter retreat, layering is key,” says Celia Bernardo, the brainchild of CeliaB. She recommends opting for a statement jacket — such as the label’s Serra Jacket — over cozy knits and sleek trousers.

Keep scrolling for more winter vacation outfit inspiration based on your destination.

The Beach

If you’re flocking to the shore in the coming weeks, ditch your rich, dark winter color palette in favor of some vibrant looks. As Jermanus mentions, a breezy printed dress won’t disappoint, as it will see you through anything on the docket, from an afternoon of sightseeing to an oceanfront dinner. Lean into the beachy vibes by accenting the number with a straw bag, leather slide-on sandals, and cat-eye sunnies.

A Ski Town

Snow bunnies are likely seizing the opportunity to hit the slopes this season. When you’re not shredding down the mountains in your high-performance ski gear, adorn yourself in soft knitwear. For a matchy-matchy look, try pairing a printed pullover with a scarf in the same shade. Ground the colorful getup with blue jeans — perhaps layered over thick tights for ample warmth. Don’t forget to snap a cute picture for the ‘gram.

The Countryside

In case you haven’t heard, countrycore looks — think barn jackets and riding boots galore — are all the rage these days. To avoid being too on the nose during your stay, style an of-the-moment scarf coat over a chunky cable knit sweater — the latter perfectly aligns with the aesthetic. Finally, punctuate the all-black outfit with a playful leopard print bag. You’re ready to pop into hole-in-the-wall antique stores or cozy up near the fire at a cute coffee shop.

A City

Perhaps you’re finally making a trip to the cool, up-and-coming city you’ve been hearing all about. An action-packed day wandering around a fashion-forward area calls for a look that’s chic but still comfortable. Traveling to somewhere cold? If so, a fur (or faux fur) jacket is a no-brainer. Make it the focal point of your look by finishing off with walk-friendly shoes, such as flat boots or sneakers. Tip: Carry a somewhat spacious bag to ensure you can bring along everything you may need throughout the day.