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After wedging 50 flights into last year’s 366 days, I am trying a new approach in 2025 — the three-legged trip. You know, the one where you leave home, visit friends or family, then jet to another destination before heading back home.
For those of us devoted to our carry-ons, mastering this higher degree of packing difficulty can either bring stress or the satisfaction of a job well done. Take, for example, my recent trip to small-town Missouri and then big-city New York that included a 50-degree temperature swing. That’s a lot to account for. And then there was the one that sent me to chilly New England for dog-sitting duties before heading to the spring steam of the South on business.
Happily, I was able to pack everything into my carry-on for each of those 10-day trips. It just took a bit of extra thought and preparation to get there.
Sticking with a carry-on may sound challenging until you consider the alternative of lost luggage. Airline-industry organizations and the U.S. Department of Transportation track the rates of “mishandled baggage,” which calculates lost, delayed and pilfered suitcases. In 2023, U.S. carriers were in the middle of the pack with a mishandled baggage rate of 5.8 per 1,000, compared to European carriers’ higher rate of 10.6 and Asia Pacific carriers’ impressive 3.0.
While those rates may not sound too bad, keep in mind that as passenger numbers rise, the total volume of mishandled bags gets much worse. In 2023, increased air travel meant 10 million more bags were lost, delayed or stolen than in 2022.
If those stats make you reconsider checking your bag, allow me to assist. These six questions are my North Star for packing a carry-on and can help guide your decisions on what to take wherever you may travel.
How can I prepare?
Avoid last-minute packing. Too often, it leads to extraneous or forgotten items. Instead, think ahead. Plan your itinerary in your head or on paper. Ask your host what they have in mind during your visit. Your selections will be affected by whether you’re hiking or dining at a fancy eatery (or both!).
And don’t forget the weather forecast. Check it daily starting at least a week out. This will give you time to launder, dry clean, hem or otherwise alter anything you plan to pack or purchase for your trip.
Does it mix and match?
This is at the core of compact packing. In the words of carry-on devotee and globetrotting comedian Conan O’Brien, “Pretend you’re Steve Jobs and bring versatile, multi-tasking clothes in a single color palette. The best picks can be worn in at least two different outfits and preferably three. Choose solids and neutral colors that can mix, match and layer together in interesting ways."
Lean on accessories when you need to make a statement. Scarves, earrings and sculptural necklaces are the easiest ways to switch things up without consuming too much suitcase space. At the other end of the spectrum are shoes — the bulkiest accessory on the list, which is why you need to limit yourself to two pairs (plus what you wear on the plane; more on that later). A single purse should suffice unless you want to tuck a small crossbody or clutch into a larger shoulder tote.
Can it swing both ways?
This is the corollary to the mix-and-match theorem. Versatile pieces that can swing from hot to cold, dressy to casual and bohemian to sophisticated are essential. Jackets and sweaters are especially well suited to this task.
My personal favorite is a knock-off jacket that looks like its designer inspiration but costs no more than half the price. With a zip-in insert (think old-school dickeys) that mimics a hooded gray sweatshirt and another that resembles a cashmere cardigan, this jacket is warm and snuggly for the plane ride but equally at home with pants or a skirt once I’ve landed.
I also packed a bright pink cardigan that topped off a black dress, a polka dot blouse (plus black slacks) and a white t-shirt (with jeans). Spiffing up that final outfit was a floral scarf woven through the denim belt loops. The scarf can also multitask around a ponytail, a head (think Grace Kelly in Monaco or Carrie Bradshaw in Sex and the City), a throat or a purse handle.
What happens if I don’t take it?
Unlike the subjective Do I really need that?, this question requires a critical assessment of your complete travel wardrobe. Break it down like this: Will leaving an item at home torpedo two or three outfits? Can I get by with something already in my bag? If I only take one pair, will I have to handwash my favorite socks or find a washing machine for my favorite jeans?
Of course, if you make the wrong call, your destination is bound to have a mall, outlet store or souvenir shop where you can find a replacement.
What am I wearing on the plane?
Once you’ve plotted out what you want to take, set aside the bulkiest pieces to wear on the plane. At the top of the list? Outerwear like a raincoat or denim jacket will take up a lot of space, as will footwear, especially any boots or exercise shoes.
How can I pack better?
Make sure your lighter-weight items and delicate pieces sit on top with heavier shoes and garments beneath. For those with rolling bags, the top is the area farthest from the wheels. If you pack a duffle bag, the first layer should be heavier items like jeans.
Once the foundation is built, move on to pack the crack. That means filling every sliver of unclaimed space around the edges, between the rolling bag handle and in zippered pockets with all those essentials you can’t stand to leave behind.
Now, sit on it, lean on it, cinch it up and cross your fingers that the zipper holds. And have a great trip without worrying whether your luggage will meet you at baggage claim!
Do you ever check a bag or do you always travel with just a carry-on? Let us know in the comments below.
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