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How to Travel Cute and Light

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When I’m planning a trip, one of the first things that enters my mind is the question, “What am I going to wear?”

I travel fairly frequently for work and for pleasure. It’s important to me to stay true to my own personal style and feel good about what I’m wearing, while also packing lightly and appropriately for the events in question.

First, two obvious tips: Check the typical weather where you’re going, as well as the projected weather forecast during your trip. Also, google to see how the locals usually dress. I’m not that fussed about avoiding looking like a tourist on vacation - I am one, after all - but I do try to steer clear of committing a major fashion faux pas when visiting a foreign locale.

Consider your travel days. Don’t wear shoes that are difficult to get on/off or uncomfortable to walk in. Pack layers, because planes often go from steaming to freezing. Bring lip balm and hand lotion on the plane to combat the dry air, and make sure your carry-on is comfortable to actually carry instead of leaving you sweating through the airport.

Think about the vibe you want to project. This will depend on YOU, as well as where you’re going and what you’re going there for. A business trip calls for a different mood than a beach vacation with your sweetheart, but there should always be elements of your outfit that make it yours alone. Your calling card could be a pair of statement earrings, outfits composed of artfully layered colors, a signature hairstyle, some combination of the above or something else entirely!

Pack as simply and lightly as possible. So many of us are tempted to bring two outfit changes for every single day, but they’ll just take up space in your luggage and confuse you when you try to get dressed every morning.

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I’m a big fan of dresses for travel, because there’s no mixing or matching to mess with - they’re one piece and done! Of course, if it’s cold you will want to pair them with tights. I love fleece-lined tights for winter and often find them warmer than wearing pants; in really cold weather, I double them. On my last trip to Europe, which took place in the autumn, I brought a few of my favorite Toad & Co dresses, a couple pairs of tights, a cardigan, and a pashmina. All I had to do was rotate the combinations. On warmer days, I wore just the dress. On colder days, I wore the tights and the cardigan and the pashmina. It made getting dressed a breeze compared to my pants-and-a-top days, and I was a lot comfier.

Think about undergarments, too: bring practical bras that play well with all of your clothes. Don’t pack the red chiffon top that needs a special strapless bra you’ll only wear once.

If you’re traveling for work, don’t forget to pack some leisure clothes. You may find yourself with unexpected time to explore the city or meet up with a friend, and you don’t want to be stuck in business wear because you were were too singleminded while packing.

Work with a unified color palette. Packing a travel capsule is exponentially easier when you shop to your season or simply have a core group of colors that you wear. Pre-PCA, packing was a huge struggle for me. My tops went with a limited number of bottoms, I couldn’t mix and match layering pieces, I couldn’t improvise outfits once I reached my destination; it was a nightmare.

Bring a lightweight but roomy bag. Small bags are light and easy, but they can also be limiting. I like to have room in my bag for a scarf or cardigan, and I also love being able to stash smaller purchases (or pastries for later!) in my bag instead of carrying them around the city in plain sight and limiting my mobility. I went to Goodwill before my trip to Colombia and picked up a knit bag with a wide shoulder strap. It was absolutely perfect for my needs and garnered compliments while I was there. A chic little backpack could be a great choice.

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Accessories quickly spice up simple outfits while taking up very little space in your luggage. A cute pair of sunnies, colorful earrings, a few bracelets, a scarf in your hair - they all go a long way toward elevating your look. For those reasons, accessories are also my favorite thing to shop for while traveling.

Bring a great lipstick for an instant upgrade to your look. Lipstick is its own magic accessory.

Condense your toiletries. Even if you’re checking a bag, full-size toiletries are bulky and heavy, and not worth bringing in most cases. I decant my hair products into smaller plastic bottles and use contact lens cases for most of my skincare, which is a huge space saver. Pare down cosmetics to the essentials.

Don’t slack on your skincare routine. Wash your face every night and wear sunscreen! Travel can wreak havoc on your skin even with the most dialed-in routine, so don’t encourage breakouts or a blazing sunburn just because you got lazy. If you do break out, I swear by these hydrocolloid patches for reducing pimples overnight.

Pack comfortable, weather-appropriate shoes. I wore a cute-enough pair of sneakers 80% of the time we were in Colombia, and I was totally happy with that, even though they weren’t necessarily the finishing touch I’d pick for an outfit at home. We did a ton of walking, and I was happy my feet were happy. In Puerto Rico I wore a pair of Havaianas Luna sandals nonstop (looove them), and in Europe I lived in my Cobb Hill booties, which are forever my go-to for stylish winter walking shoes. Depending on the length of your trip, it’s a good idea to bring 2-3 different pairs of shoes so that you can rotate them out if you start to experience any discomfort. But once again, make sure they go with everything. It’s a huge pain when you can only wear certain shoes with certain outfits - you want an entire buffet of shoe/outfit options!

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Stick with what’s tried and true. Your vacation isn’t the time to test unfamiliar hair products or skincare, break in brand new sandals (trust me on this one), or experiment with a whole new look. If you need to, spend a few weeks before your trip “practicing.” If you bought new shoes, wear them around the house for a while each day to make sure they aren’t going to rub your heels raw. If you need an easy hairstyle for the beach, YouTube some hair braiding tutorials. Don’t pack a bunch of clothes you’ve never worn before; chances are they may not wear the way you expected them to.

At the end of the day, remember that you’re there to savor the experience of another place, not to look good. For whatever reason my hair behaved terribly in Colombia, falling flat and feeling gunky more days than not. I wasn’t happy about it, but I just washed my hair more frequently and didn’t let it disturb my mood. Accept that some days you might be wearing a basic tank top and shorts because it’s ridiculously hot or you’re going exploring in the rainforest, or maybe because how you look on vacation isn’t a priority of yours whatsoever, and that’s totally fine too.

My style coaching clients frequently ask for my help with building travel capsules, and it’s one of my favorite problems to tackle. If you’re trying to build a capsule wardrobe for regular life, I can help with that, too!