BLOG // 20 Things I Can’t Fly Without

Published on on March 27, 2017. RoundTrip is a travel blog with a conversational tone dedicated to helping readers discover new places to love and new ways to make travel more enjoyable.

If you want to know what you need to pack in a carryon, don’t worry—Pinterest has about 50 bazillion options of what you must bring in a carryon. But guess what? We all know that no two people are the same, and one of the beauties of travel is that no two trips are the same, so there’s no one-size-fits-all list for a carryon packing list. So while I can’t pack your suitcase, here’s what I can do for you: I can tell you what I love wearing on a plane and stowing under the seat in front of me on a plane (with a focus on my most recent trip to New England) and hope that it sparks some inspiration for your own packing list. Here’s what I packed for two-flight journey from mild spring weather to total winter weather with an hour layover, which worked just as well for my one flight home. (Note: Some of the exact items I brought are no longer available to buy, but I have found similar items.) 

We can’t all be airport style icon Rosie Huntington-Whitely who changes into more comfortable clothes once she boards a plane so she can dress as trendily as she wants for the paparazzi. Actually, I’m not sure how Rosie Huntington-Whitely has the energy to be Rosie Huntington-Whitely, but all power to women who have the dedication to keep their careers in mind even when they travel.

But here’s my confession: I am not like that at all—comfort and minimizing extra baggage are my priorities even when I travel for work. How to do that? Think LAYERS, my friends. If the temperature of your day changes noticeably from home to your destination, you’re going to need them. You might also need them if, like on my journey home, the freezing temperatures in the air outside are making your feet go numb in your favorite window seat. Fortunately, I was good to go with this outfit (which I wore both traveling days—a great way to save room in my suitcase!):

  • Light jacket (Target) – My go-to outerwear in spring and fall. It zips and it snaps, which gives you options for how secure you want your outer layer to be. Deep pockets let you throw your phone in without worrying it will fall out, and the hood unzips to reveal a hood for rain, another nice perk when you’re not sure what the weather will be when you land. Another must for me: It’s thin enough to stuff it in my backpack if I don’t need it.

  • Stud earrings (Kate Spade, by which I mean the Kate Spade outlet) – Because I am not going to worry about dangly earrings getting in my way when I am adding and removing layers. I usually only pack 2-3 pairs of earrings max on any trip (including what I wear on the plane), but I try to make sure they all work relatively well with any outfit I packed some I have some options.
  • Thin infinity scarf (American Eagle) – This infinity scarf is my jam. It keeps my neck warm without making my head feel like it’s in Florida while the rest of my body is in Michigan, and it’s thin enough to fold up and put in my backpack if I don’t need it. Bonus: Infinity scarves don’t have tails that get caught in your jacket, backpack or the spinning baggage claim turnstyle.
  • Thin athletic sweatshirt (GAP) – Comfy is the name of the game here. The pockets actually aren’t that helpful since they’re so shallow, but the thumb holes make it easy to put on my light jacket without bunching up the sleeves. Also, the bright pink color brightens my day, too.
  • Short-sleeved shirt (Target) – Short sleeves keep the sweatshirt sleeves from feeling bulky, but the the long length is nice so I don’t have to worry about my shirt riding up when I’m reaching to put my carryon in the overhead bin or bending over to pick up my suitcase.

  • Joggers with zip pockets (Target) – Pockets FTW again. Stick your chapstick, phone, headphones or whatever in there without worrying you’ll lose them.
  • Keds – You might be noticing I have an obsession for Target-woven goods, but I gotta tell you about my incurable Kedsession, too. These shoes are great for walking, cute and super easy to slip on and off when the TSA wants to check out your socks.
  • Athletic socks (Target) – Speaking of socks, I’m normally a big fan of no-show socks with Keds and other low-rise tennies, but when it comes to plane couture, I opt for low-rise athletic socks that are warmer and don’t have a pesky habit of slipping off the back of my heels. (Unless you can recommend a better brand of no-show socks—I would be forever grateful.) And if someone judges you because they can see your socks, you probably don’t want to be their friend anyway. 

Maybe some of those pieces aren’t your style, but let me stress the most important principle here for all plane outfits: Wear LAYERS.


While I’m usually a big fan of crossbody bags because they free up your hands, they usually aren’t big enough for me when I travel. The bigger solution to keeping my hands free? A backpack, which doesn’t put all the weight on one shoulder, and the top handle is easy to stick over the handle of my suitcase so I don’t even have to keep it on my back. I fell in love with this backpack when I saw it in Barnes & Noble before I went to the Sundance Film Festival in 2013, and it has become one of my most favorite companions on planes and in Starbucks. For more ways to style your travel backpack and decide which bag type is best for you, click here. Here’s what I packed in my backpack:

  • Another sweatshirt (Totally Good Time) – Did I mention LAYERS are important? I packed another bulky sweatshirt that would slip on over my thin sweatshirt. Bonus: The Gilmore Girls design makes me smile every time I see it.
  • iPhone 6s (Apple) – Duh. Bring your phone, and download some music and games that don’t require the Internet before you  go.

  • Headphones (Apple) – Also duh. I prefer earbuds over fancy Beats because 1) Cheap and 2) Much easier to stuff in my backpack or pockets. Hate when they get tangled? This pin actually lived up to the promise of changing my life.
  • An extra long charging cord ( – If you’re competing for outlets, there’s a good chance you’ll end up standing/sitting next to some other travelers. It’s only as awkward as you make it, but a 5’ charging cable like this one makes it much less awkward because then you don’t need to accidentally snuggle with someone you don’t know. Bonus: The cord also came with a car charger and a wall charger.
  • iPad Pro (Apple) – This was my very first trip with my new iPad, and I loved how much lighter it is than my laptop. I can’t recommend a case with a built-in stand, stylus pen and a keyboard enough—so great for getting some work done (like starting blog posts about your travels).
  • Two Magazines + Book (InStyle and Talking as Fast as I Can by Lauren Graham) – Because I like options, and traveling is prime time for catching up on reading for me. (Oh, the things you can accomplish when you’re not distracted by the Internet!)

  • Wallet (Vera Bradley) – Duh again. But I’ve also discovered the change zip pocket is a great place for bobby pins and medicine to fight headaches and travel sickness.
  • Cosmetic bag (Kate Spade, see my previous note above about the outlet) – The only gripe you might find with my beloved backpack is its lack of pockets. The front zip pocket and two side pockets are awesome, but there’s no built-in organization in the main compartment. So I always pack the little stuff like this in one…
  • Hand sanitizer (Up & Up from Target) – Make the airport happy and listen to all of its PSAs about killing germs on your hands.
  • Tissues (Up & Up from Target) – You don’t think about them until you need them, and then you can’t stop thinking about them, especially if you don’t have them.
  • Important Personal Items like meds and feminine products – You really need to know where these are. Like, always.
  • Gum (Orbit) – Because ear-popping is the worst.
  • Travel-sized lotion (Gold Bond) and Chapstick (Vaseline) – Nothing makes your skin dry up like changing altitudes. They also don’t take up much space in your quart-sized liquids bag you have to get through security.
  • Quart-sized baggie (Ziploc) – Speaking of which, don’t forget the TSA’s rules about liquids when you travel. I’ve noticed airports haven’t been checking these quite as closely as they used to, but it would sure be a bummer if you had to pitch your favorite lotion or moisturizer if you forget about it.

  • Granola bars (Lärabar) – I try not to think too hard about how much of my diet is made up of granola bars, but I’ll keep eating them until they stop being such filling and yummy snacks. They’re still good if they get squished, and don’t take up a lot of room in my backpack.
  • Water bottle – I like to get a disposable one so I don’t lose one I love. Don’t worry—I recycle them when I’m done with them!

{Access the printable packing list here!}

Happy travels,
Taylor Blake

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