The O.G. Overnight Bag, $295
Read our full review of The O.G. here.
The O.G. Overnight Bag has quickly become my go-to personal item on flights. Its suitcase-handle sleeve is a game changer; now I can rest assured that when I rest my personal item atop my carry-on it won't fall off. Inside the bag are some even cooler features, like a padded laptop sleeve, a separate shoe compartment, and tons of pockets for organizing everything from my pens to my earbuds. The O.G. also comes with a messenger strap for easy and comfortable carrying across your body or over your shoulder, and it's made of a durable and water-resistant nylon, so there's no need to worry about it being ruined by coffee spills or bad weather. — Ellen Hoffman, director of content strategy for Insider Picks
With all of all the smart features, I've found I'm able to fit just about everything I need for a weekend away in this one bag, unless it's winter (because sweaters and coats are just too bulky). Even though the bag is so structured, it's really lightweight, making it really easy to carry, even when loaded with clothing and toiletries. While pricey, I think it's worth the $295 investment. — Remi Rosmarin, Insider Picks reporter