I try to carry on all my bags whenever possible. I recently packed for a 5-day winter trip to Boston with only a large purse and a rolling 22″ carryon. But whether you check or not, your purse/handbag/personal item needs to be strategically packed because let’s be honest, you never know how long you’ll be in an airport or worse, on an airplane.

These are our must-haves for any carryon bag:

• Reading material: duh. Even in the age of iPods and other electronics, who knows how long you’ll be sitting on that jetway unable to use “any and all personal electronic devices.”
• iPod and headphones: I download my favorite shows from iTunes so that I can catch up on anything I missed during the week.
• Pashmina: Any large shawl will do, but we adore the size and bright colors of the pashmina world. It serves myriad purposes from a blanket on the plane to a scarf when traveling to cooler climates.
• Socks: Besides being useful for particularly icky security line floors, socks will come in handy at 30,000 feet where the air is quite chilly. On long flights, your feet will swell and you shoes may become uncomfortable. Here, socks are necessary because seriously, no one wants to look at your feet, no matter how pedicured they may be.
• Small cosmetic bag: In it, keep intense moisturizer, small tube of eye cream, lip gloss, makeup compact (we at Traveling Sisters particularly like Trish McEvoy’s credit-card-size carry case), bandaids, and anything else that would help you should you be delayed for a significant amount of time.
• Medication: This is one of those things that is so obvious it should go without saying, but Traveling Husband often packs his medication in checked luggage for reasons unfathomable to me. Don’t do it. Your flight will be delayed and/or your luggage will be lost. And then where will you be?
• Cell phone charger: It’s so easy to pack this one in your suitcase, but it’s critical for your ability to communicate should you be delayed.
• Water: Yes, I know you can’t bring it with you from home. But buy a bottle when you get through security. You can also bring those on-the-go packets that make flavored low-calorie drinks. I’ve been stuck on the tarmac quite a bit lately, and have been quite glad to have a bottle of water with me.

One of the best investments you can make is a travel bag that is both stylish and sturdy. You can get them from Target to Bergdorf Goodman’s, as long as you like it and it fits everything you need.