Photo: Connie Park

Updates writer Gabriella DePinho calls herself a “frugal flier.” She is no stranger to sacrificing early seat selection, skimping on legroom, or boarding dreaded red-eyes for cheaper airline tickets. But the hardest thing for her to swallow has been flying without a carry-on suitcase.

With certain airlines introducing some carry-on fees, it’s becoming more and more useful to know how to squeeze what you need into a free underseat bag. To find the best strategy for doing just that, Gabriella packed, unpacked, and repacked test bags four times.

Our strategy for packing very, very light→

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Photo: Marki Williams

Of course, just about any bag can be considered a personal item, as long as it fits under a seat. But having a great dedicated one can make a big difference in packing and traveling smoothly. After our latest round of testing, we have a new pick: A luxurious shoulder bag that comes with detailed organization and add-ons made specifically for simplifying travel.

It holds more than any bag of its type we tested→

The gadgets we bring on every trip The best chargers, power banks, noise-cancelling headphones, and more→

“Here’s my secret to fitting twice as much stuff in my luggage” Two words: packing cubes→

An (actually comfortable) travel pillow we love Its tall memory-foam walls offer more support than any other pillow we tested→

Illustration: Dana Davis; Photo: Jackie Reeve

The pleasant squeeze of compression socks is meant to help boost circulation, which can be helpful for flying. It isn’t a magic health fix or performance enhancer, but it can feel fabulous. And for senior staff writer Jackie Reeve, this pair—which comes in delightful colors and is easy to take on and off—is also an essential part of her daily gardening uniform.

They pair nicely with her “I work hard so my chickens can have a better life” T-shirt→

Have a great weekend.

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