Ask anyone who lives in a cold climate and they’ll tell you that winter’s frigid weather is really only tolerable during the holiday season when there’s the distraction of festivities. Once January hits, it’s an uphill battle toward spring (from a temperature perspective, at least). Unsurprisingly, a popular activity during this time of year is to book a vacation in a tropical climate. Destinations like the Bahamas and Mexico are beautiful year round but especially enticing when your space heater is working overtime and you can’t bear the sight of your giant puffer coat any longer. If you’ve already booked your warm-weather vacation (congrats), you might have realized that traveling from a chilly environment to a humid locale makes dressing and packing for a beach vacation even more of an obstacle.
For example, if you’re departing New York City on a day that’s 20 degrees, you simply have to wear a coat to the airport. But once you arrive at, say, Antigua, that coat is going to feel like your own personal sauna. Thankfully, there are experts who know a thing or two about warm-weather vacations during winter, like Coco Shop founder Taylor Simmons and celebrity stylist Tara Swennen (whose clients include Kristen Stewart and Allison Janney). Ahead, get the download on their dos and don’ts surrounding the topic, and shop any vacation pieces your suitcase might be missing.
Do: Adopt a Travel Uniform
You’ve heard it before but it warrants repeating: a travel uniform is the key to no-fuss flying. If you have a general idea of what to wear on the way to your far-flung destination, you’ll always have one less thing to stress about. “I have a travel uniform: beige flats, white or off-white denim, and a striped t-shirt underneath a turtleneck sweater and jacket,” Simmons says. “Your feet might be chilly in the beginning, but you can take off your sweater and jacket when you land and look cute and comfortable as you deplane. It has never failed me.”
Don’t: Underestimate the Importance of Fabrics
The biggest sartorial fumble you can make while on a warm-weather holiday is to have clothing that doesn’t breathe. “For warmer climates, opt for cotton, linen, or rayon as these are light and airy fabrics that dry easily, absorb sweat, tend to be somewhat wrinkle resistant, and most importantly will keep you cool,” Swennen says. "Lightweight and airy jumpsuits or maxi dresses make putting together an outfit quick and easy.”
Do: Go Big On Clothes
If you’re the type of person who is content with packing a small handful of items for your tropical vacation, by all means, keep things minimal. But if you live for a look, Simmons says to focus your packing attention away from accessories and toward the actual clothing. “I go big on clothing — big dresses, wild dresses, lots of dresses, some sets,” she says. “With separates, I never feel like I pack quite the right coordinating option, but in a dress, I feel put-together and elegant in the two minutes it took me to get ready. I bring a selection of earrings, too, because they take little space in my carry-on and can update a dress.”
Don’t: Overpack Shoes
Both experts agree: you don’t need that many pairs of shoes. “Don't overpack shoes. Try and choose a great sneaker, one or two flip-flops, one heel if needed,” Swennen says. Simmons notes that she seeks efficiency and versatility in her vacation footwear selection.“I bring one or two great, beige sandals to go with everything I’ve packed.”
Do: Wear Your Heaviest Items On the Airplane
You’ll most likely be doing this anyway because you’ll be transferring to the airport in cold weather, but Swennen recommends keeping your heaviest items on your person to avoid overweight luggage. Besides, planes are infamously cold, so it will be nice to have an extra layer or two for the journey there and you can easily tuck them in your bag once you’ve landed.
Don’t: Bring a Hat
Straw hats for vacation are, in theory, a good idea. But realistically, they’re not worth the hassle. “Leave behind your straw hat (unless it's a really special one),” Simmons says. “I find that they are always harmed in my suitcase or the overhead or they make the trip a pain in my lap. You can easily find one when you arrive at your destination.” Or, try a baseball cap or soft bucket hat which will more easily squeeze into a suitcase.
Shop Warm Weather Vacation Essentials
We only include products that have been independently selected by The Zoe Report's editorial team. However, we may receive a portion of sales if you purchase a product through a link in this article.