Traveling Like A Pro: Updated!

With the holidays right around the corner, there’s a lot of traveling for some of us. Whether we’re going home for the holidays or have short work (or play!) trips to attend, the fall/winter months are when most people are out and about. Luckily for me, I get to spend Thanksgiving at the beach. There will not be much of tanning going on, but that doesn’t mean it won’t be fun.

When thinking about traveling for a long weekend, packing can be the most stressful thing ever. If you’re anything like my boyfriend, he loathes packing. I end up doing it for him, most of the time. So with two bags to pack, instead of just one, I have a lot to do. Thankfully, I have my traveling like a pro checklist to keep me in track. Have you heard of the 5,4,3,2,1 method before? It’s the best (and the only) way I know how to pack.


You may be familiar with this approach, because I’ve blogged about it before. It’s pretty self-explanatory: five tops, four bottoms, three accessories, two pairs of shoes, and either one tote bag or a bathing suit depending on the season. The reason why I love this method is because I used to always pack a ton of different options because I never knew what I’d be in the mood to wear once I got there. The truth is, I never ended up using half of what I packed. Packing doesn’t have to be that stressful if you have a plan.The key is to pack with a theme in mind so that you can mix and match your outfits. Maybe you’ve heard of capsuling before; it’s sort of the same thing. If you plan ahead, you’ll have plenty of options for when you get there.

Now that we’re well into the colder months, sweaters and boots can take up the majority of your space in a suitcase or luggage bag. The struggle is: how to pack light when your clothes are so heavy. Here are some quick tips for packing during the fall and winter months:

Stick to neutrals – Since sweaters don’t need to be washed as often (you’re not sweating in them like you are a tank top on a 90 degree day), you can get by with fewer tops. Stick to neutral colors and use your accessories [see next item] to change up your look. Since you’ll most likely be in and out of museums, shops, and restaurants, chose warm cardigans and a light long sleeve t-shirt so you can layer, and un-layer, as necessary.

Functional accessories – Scarves are a traveler’s best friend.  Choose a bright color to compliment your neutral wardrobe. I often throw in a vest to add an extra layer of warmth to wear both on the plane and when out and about. Other than the earrings I wear on a daily basis, I don’t bother to pack any unnecessary jewelry.

All hail the leggings! – As if you needed reminding that black leggings are the savior of any trip. Not only do they pack well, but they take up limited space and match everything. Take it one step further and make sure yours are fleece-lined and have enough substance to keep you warm. On a really chilly day, wear them under jeans for another coat of warmth.

Shoes for the elements – Shoes should be all about functionality. You don’t want to slip and fall on ice, so leave those beloved booties at home. Find a pair with good traction and an appropriate material for warmth and durability. Heavy socks are ideal, especially wool ones that won’t soak up moisture. I also like to bring my light weight sneakers to slip in a workout if I can find a gym nearby. Wear your boots on the plane to save space and tuck your other pair into a plastic bag to keep your clothes dry and dirt-free.

Every nook and cranny – Stuff undergarments into your shoes. Roll pants tightly and tuck socks into open crevices. Wear your bulkiest items and be realistic with what you bring. Make sure you pack your heaviest items (sneakers, thick sweaters, etc.) towards the bottom of your suitcase where the wheels are, it’ll help prevent it from tipping over when upright!

Surprise visitors – Although you might be dreaming of fluffy flakes and snow covered trees, Mother Nature is not always so kind. It just so happens that I was greeted on New Year’s Day in Chicago with a downpour. Make sure you pack a tiny umbrella to not only protect you from the rain, but to keep you dry in case temperatures reach freezing later on.

And that’s it! You’re ready to travel like a pro!

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