How to Pack So You Never Have to Check a Bag

It’s not impossible! Sharon Ainsberg shows us how.

By: Sharon Ainsberg

If anyone saw the 2009 film Up in the Air starring George Clooney, his character, Ryan Bingham, is pretty much the best example of why not to check a bag (you lose “35 minutes per flight”). Or remember in Meet the Parents, when Ben Stiller tells the flight attendant that the only way he’ll let go of his bag is if she tries to pry it from his dead, lifeless fingers? Well, that’s me. (“If you can get it from my Kung Fu grip, then you can have it… Otherwise, step off, bitch.”)

Checking a bag should only be done when massive amounts of shopping have ensued on a trip (this is encouraged) and you are left with absolutely no choice. I’m on a plane every 4-6 weeks for business trips on average each year, and I haven’t checked a bag since I bought Mexico City out of all its tchotchkes.

But if you’re a woman packing for one—meaning just yourself, no kids—and even if you are going away for 10 days, you do *not* need to check a bag, and you can still look flawlessly stylish. I’ve mastered the art of the two-carry-on policy for what is going on 20 years, and I am here to convert you and save you time, money and frustration.

Everyone is so busy worrying about “having options” on a trip, but I promise, you won’t feel deprived if you follow my rules. You’ll feel liberated from the extra weight and hassle.

 

Let’s start at the beginning: THE BAG(S).

You’re allowed two—one that fits under the seat, and one that fits in the overhead length-wise, wheels in. You want your under-seat bag to be big enough to hold a smaller handbag in it; and that smaller handbag is your go-to for the whole trip. You want something chic, neutral and lightweight—I recommend a small crossbody, like this Balenciaga Papier Triple, or this Kate Spade Cobble Hill Straw crossbody.

The larger, under-seat bag will double as a beach bag if you’re going on a beach vacation, or as your tote bag if sightseeing and/or shopping. I like burlap and canvas varieties, but the key to the under-seat bag is the “mush” factor. You don’t want this bag to have structure. It must be able to mush effortlessly. I carry a Balenciaga Motocross Classic Weekender I bought at a consignment shop for most of my plane rides, but I also love this color-block zippered canvas tote by Pacific Tote Company, which can easily double as a beach bag.

 

Now. About the overhead:

I swear by my bag, but it’s on the pricier side. However, with the amount I travel, it’s worth every cent. I use The Salsa Deluxe by Rimowa, a 360 spinner with the lightest hard case and amazing internal organizational features to keep things in place. This size works on around 97% of planes. If spending $600 on a carry-on is out of the question (which is totally understandable), then opt for the same genius, lightweight construction for about half the price with a Raden A22, available in a dozen different colors.

 

So let’s move on to packing:

This is what most people consider the real challenge, and I’m going to break it down for you. It all begins with the shoes. Yes, your beloved shoes—be prepared to part with most of them, because they’re the enemy of your otherwise perfectly capable carry-on. Instead of quantity, traveling with shoes is all about quality and practicality. You want to build your trip and your entire wardrobe primarily around two pairs of shoes. One heel or wedge-type (only if necessary), and one flat or lightweight white sneaker you can wear with everything. Flip-flops hardly count—they can fit anywhere. If you need to travel with running shoes, make them some kind of lightweight knit crushable sneaker like these Nike Flyknits.

Once you’ve picked your shoes, build your wardrobe around them. Pants, shorts, dresses, skirts and tops that all easily work with each other and, most important, with the shoes.

Pack your shoes on the bottom of one side of your suitcase, then roll your clothes rather than folding them, to avoid crease marks and to save space. You’ll be surprised with what you can fit if you roll and tuck.

Top everything off with some easy jewelry and accessories that travel well on your body. Everything you bring should be easily replaceable (don’t bring your expensive rings or anything that has emotional value or is rare or irreplaceable—you can part with these things for your vacation and keep them safely tucked away at home). Don’t bring anything you aren’t willing to lose!

Finally, and this is a big one: your vanity kit. Minimize it all—bring your most basic makeup: a neutral and a red lip color, mascara and curler, a small tinted sunscreen moisturizer, and maybe a small portable bronzer and brush. For body and hair products (sunscreen, moisturizer, shampoo and conditioner), chances are they sell it where you’re going, or you can buy some travel-size options at the airport. If you’re traveling internationally, it’s fun to explore some of your favorite brands and what glam concoctions they may offer overseas that you can’t find at home!

That about covers it—have an amazing summer, and safe travels to all!

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