What to Wear: Traveling to a Tropical Location in the Winter

Hi Friends!

So this winter will be an exception because we need to avoid Zika because I’m pregnant. But in previous years, Chris and are usually ready to book it out of here by January. I ~~like~~ accept winter in Chicago until Christmas/New Year. Around mid-January, it’s already getting old, but wait, there’s 3 more months until it warms up.

In the past, we’ve booked long-weekend trips (Friday-Monday) to Mexico and Jamaica at the end of January or February, and it makes a world of difference! It’s just so nice to wear a dress, get some sunshine, and just feel warm for a few days. Similarly, in 2017, we went to Dubai for our honeymoon in January. We’ve also gone to Florida, and this year, when we left for Australia in April, it was still freezing in Chicago.

What’s one to wear when you’re traveling from a location where the temperature is 15 degrees, to vacation where it’s 85 degrees? And not waste precious luggage space? Today, I’m sharing what to wear when traveling to a tropical location in the winter.

I’m a notorious over packer (according to Chris), but I swear I try not to be. Imagine what would happen if I didn’t try to make each item work several times. Double duty!

1. Maxi dress – If you can wear more on your person while traveling, the more luggage space you save! I used to wear a long tee on the plane (with leggings), but I rarely re-wore it on vacation. Why not wear a maxi dress that can take you through a day of sightseeing or even a casual dinner? This one is from Indigenous, and made of fair-trade, organic cotton.

2. Leggings – I never fly in jeans…I don’t find it comfy! Leggings are the way to go, but I remember being SO hot when we arrived in Cancun one year. It was around 2 hours before we got to our resort and I was able to change. I love the idea of wearing leggings under my maxi dress when I’m in Chicago, and then taking them off in the airport restroom at my destination. This is MUCH easier than trying to change into a completely different outfit. And if you happen to want to fit in a workout at the hotel gym, you have workout pants! I would never go to the gym on my own on vacation, but Chris still goes, so a few times, I’ve gone with him. But I have done yoga with my girlfriends on vacation, which is more fun than hitting the treadmill.

3. Comfy walking shoes – This is totally necessary for me, this Chris and I are almost always late and need to sprint across the airport. I know, we need to be better. But also, it’s good to have shoes for long days of playing tourist. If you are planning to work out, you could wear shoes that’ll double as your gym shoes.

4. Scarf – It’s fun to dress up a black dress with a colorful scarf. My scarf keeps me warm while traveling, and doubles as wrap on vacation, or a sarong at the beach or pool.

5. Light Jacket or Cardigan – Even tropical locations can get chilly. I’ve gotten overly excited about impending and not packed anything lighter than the winter coat I wore to the airport. Bring a light jacket to wear over your sundress, or at least a sweater or cardigan. Even better, wear it over your maxi dress on the plane. I’m wearing my first ever denim jacket that I’ve owned since I was a kid.

6. Large Tote/Carryon – I’m carrying the Lo & Sons OMG bag (I also have the OG, which is slightly bigger). This serves as my carryon, but I can empty it out at the hotel, and carry my water bottle, sunscreen, beach essentials, or camera for a day of sightseeing.