The main struggle to pack for a trip comes down to uncertainty. Not knowing what to bring with you. If you aren’t confident in what you have in your backpack or luggage — or feel like you didn’t bring the right thing — your trip can suffer. Sure, you’ll survive without a raincoat or basic t-shirt layers, but any kind of discomfort will detract from your travel experience.

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This uncertainty can often become overwhelming, leaving travelers mentally paralyzed, confused, and all of a sudden throwing five dresses they won’t wear into a bag and bringing seven pairs of shoes (just in case). Those are the overpackers. On the other side of the spectrum, you have the underpackers — those who aren’t quite sure what their destination will require, so they just pack a few items and end up wishing they brought something nicer or a warmer layer.

For any length of trip, you should start thinking about what you need to pack about a week to two prior. Personally, I use the notes feature on my phone to write down items I’ll definitely need and add as something else comes to mind. For clothing, I type out all of the days I’m there as well as any specific events (dinners, nightlife outings, excursions) where I’ll need to have a better idea of what I’m actually going to wear.

Starting at least 10 days in advance gives you time to order that packable straw hat you need for your cabana in Tulum or dry clean the blazer that’s been sitting in your closet, for several months. For your own list, I suggest typing out literally everything you’ll need to pack, including a toothbrush, extra contact lenses, and a brush. That way, when it’s the night before your early wake up time, you’ll feel more relaxed and assured you’ve remembered to pack everything you’ll need.

How do I pack differently for travel since Covid?

I’ve flown several times since the start of the pandemic and for me, it’s all about the efficiency of your personal item bag. I like to have all of my essential items — passport and travel documents, credit card, extra mask, hand sanitizer — in a secure but easy-to-access area. I want to get from Point A to Point B as quickly as possible and not spend any extra time fumbling around my bag looking for my ID, holding up the line in the process.

What is a packing hack I swear by?

I’m a recent compression packing cube convert. For the longest time, I didn’t believe in the hype, choosing to simply roll or pack my belongings in my bag. Since investing in a set of compression packing cubes, my entire packing process has become more organized. Depending on the trip and what I’m bringing with me, I’ll either pack designated outfits together, use the cubes to hold shoes I don’t want to get scuffed up, or group similar pieces (like bikinis and coverups) together. At the end of my trip, I’ll use one cube to house all of the dirty laundry — which also makes unpacking a breeze.

What’s one trick I use to save space?

Along with making a packing list beforehand and using compression packing cubes, I’ll do a version of the famous Coco Chanel quote: ‘Before you leave the house, look in the mirror and take at least one thing off.’ That means I’ll lay out everything I plan to pack and decide what one or two items I can leave behind. Do I really need two sweaters? Will one do the trick? Same thing for toiletries. I can usually survive a five-day trip without both face moisturizers.

In fact, now, when I fly with my carry on, I bring a travel-sized version of an all-in-one product. Augustinus Bader’s The Cream comes in a 1-ounce bottle, and while on the pricier side, it does the work of a handful of products, including my Vitamin C and anti-aging serums and moisturizer. Fewer skincare products in my carry-on, more room for everything else.

What is the worst packing mistake people make for a long trip?

Being a recovering overpacker, which is a result of previously having a wardrobe full of standalone pieces. This type of clothing inhibits the efficiency of packing, especially for a long trip. Instead, invest in classic, versatile separates that can be mixed and matched. That way instead of filling your checked bag with all of the dresses, tops, and pants you think you’ll wear, you’ll be creating an on-the-go closet that can easily be mixed, matched, and create a number of different outfits. For this type of clothing, I turn to brands like Paige, Aqua, and Vince Camuto to round out my travel uniform.

What about for a short trip?

The worst packing mistake for a short trip is definitely packing too many shoes. You’re there for two to three days, max, you don’t need to bring any more than three pairs. The location and season will, of course, affect which shoes you bring, but it should be a relatively similar formula. In the summer, a nice pair of leather sandals (that can be dressed up or down) will take you a long way, similarly to a pair of smart boots in the fall and winter. The travel sneaker is an all-season must-have — perfect for exploring your destination — and if you have room for one more, a block heel (or loafer, for gentlemen) for dressed-up occasions will do the trick.

What is the worst packing mistake you yourself have ever made, and what did you learn from it?

I was 20, traveling to London for a long weekend in October. Not only did I bring both a large Nike duffel bag and a backpack full of items I was never going to wear, but I didn’t bring a coat. I assumed that 60 degrees Fahrenheit meant warm… I thought wrong. Not only did I not have the proper attire, but I packed a pair of 5-inch heels to wear at night. If you’ve ever experienced heels on 1800’s cobblestones, you know this was a terrible idea. Long story short: I’ve learned to think through the packing process more thoroughly, wear more practical heels, and always, always double check the weather.

One more, because I’ve found myself in this predicament a few times. If you’re traveling out of the country, you’ll have to fill out a customs or entry form. Always have a pen in your personal item or carry-on. No one wants to be that traveler waiting around for an extra pen or asking fellow passengers if you can use theirs once they’ve finished.

What is your go-to carry-on suitcase?

I’ve used several brands of carry-on suitcases, but the Coolife carry-on has been my favorite of the bunch. The multi-directional, silent, spinner wheels are sturdy and the spacious interior and lightweight design hasn’t let me down yet. Plus, I can confirm it holds at least one or two outfits more when using the compression packing cubes. I may have learned to be a more efficient packer, but I’ll still veer toward overpacking if I’m in a pinch.

Any other packing accessory must-haves?

For many travelers, nailing down the perfect airport look — equal parts comfortable and put-together — can be a struggle. I don’t want to wear leggings and sweatpants because they usually don’t give off a professional vibe. I personally swear by an oversized blazer (which is usually the perfect layer for airports and airplanes), a classic tank top or t-shirt, and a nice pair of Paige denim jeans. If you’re headed to a work event, you look the part, but if you’re jetting off to a vacation destination, remove the blazer, throw on your shades, and you’re off.

I hope this helps you pack with a bit more confidence on your next trip. But if the worst does happen, remember that it’s the nature of travel to present you with surprises. So pack your bag as well as you can, strike out on an adventure and let the chips fall where they may.

Until next time!

Be safe … PEACE