Traveling with Kids: A Guide for Looking Fly in the Sky

This week we flew to Virginia for an overdue visit to see family and loved ones!

That’s right, you read it correctly- we flew. With a 4 year old, 2 year old, and 4 month old. 3 little boys, 3 car seats, and 9 days worth of luggage. The word “daunting” probably describes our vacation anticipation best.

But you know what? We couldn’t have asked for the flight experience to have gone better.

The boys didn’t make any mad dashes through security. Our checked suitcase hit a high-five worthy 48.8 lbs. And, although this was admittedly tempting, we managed not to lose any children to the baggage claim carousel.

Could it be the perfect flight…?! Does that sound too good to be true? Of course.

Even with the smooth flying, there were things! Baby Hugh got his hands on my wine glass at the airport bar and spilled it all over both of us (definitely his fault, not mine). We had to mad dash to our gate when we overestimated the time available to order a second round, arriving smelling like spilled wine. The baby pooped as we started to take off and we couldn’t get up to change him for a dangerously long period. And obviously, there was spit up everywhere.

Lesson here? Even when the kids behave so well that it seems like fiction, they’re still kids. And that means you are going to have to adapt some of your travel plans for them- outfit not excluded. Here are a few guidelines to follow when traveling with kids to help you look fly in the sky!

Comfort: Air travel requires both mobility and being able to sit in one place for an extended period of time. You want to be comfortable! No, I do not mean wearing pajamas to your flight. That would be awfully hypocritical of me, wouldn’t it? No- there are plenty of easy pieces out there that have just as much comfort as true loungewear, but look infinitely sharper.

Dark Colors & Busy Prints: Let’s be real. The likelihood of me spilling my drink on myself during turbulence is give or take about 100%. Flying with my kids? Triple that percentage to 300%, no turbulence required. And that’s just the drinks. Wearing clothing that will disguise mishaps will preserve your stylish jet setter presence!

Something Warm: Not sure who decided the temperature of a Chicago winter was an inviting environment for flight travel, but being that as it is, you’re going to want to plan for the brisk in your outfit. Layering is the perfect way to go, since running around the airport and sitting on the plane during boarding can get warm. Cardigans, oversized scarves, and knit jackets are easy on and off ways to add warmth, and can all serve as a makeshift baby blanket if needed!

Smart Shoes: A big day of flying also means a big day for your feet. Lengthy security lines, far away concourses, and sprinting to your gate with a child on your hip will put your tootsies to the test. Comfort and ease are critical for your travel footwear. Closed toed shoes are a wise consideration to protect your feet from getting clipped by rolling suitcases . If you will not be flying with any special clearance, choose shoes that are easy to slip on and off during security!

Jewelry: Jewelry can be the ultimate tool to jazz up your outfit, but traveling is a good time to be selective. Hoisting heavy bags over your shoulders can catch a low hanging earring. If you’re going to have a lap child you want to take extra precaution- extended periods at grabbing distance is just asking for it. Seek out “durable” necklaces and statement studs that will give you a lot of look with less risk.

Bags: If you’ve flown with a diapered child, you know that diapers and wipes are as critical to have readily on hand as your boarding pass. Every one of my children has mastered the art of blowing out during the plane flight. The last thing you want is frantic searching for diapers in an overhead compartment, a struggle to haul out an oversized bag from under the seat, or looking for an accessible place to set down your bag in the teensy bathroom cabin- all with a diaper situationed baby in your arms. Having a smaller sized bag with the essentials - a few diapers, wipes, a back-up outfit, phone, wallet, and lip gloss- will make your flying experience much less turbulent.

Some parting thoughts-

If you have a child that is prone to motion sickness, have your husband sit with them. If there is an incident during turbulence, your outfit is more important than his.

Matching your kids isn’t just for cute pictures. Airports are busy, and children are slippery. If you find yourself trying to put eyes on a runaway, only having one outfit to remember makes life easier.

Ordering a drink on a plane is asking for it. Those tray tables are begging to be knocked into. If you’re thirsty, order something that will allow you to screw the top on and off between small pours. Like airplane bottles!

See below for my favorite Fashion Finds for looking Fly in the Sky!