#KERRentlyTraveling Carry-On Challenge

Who knew that my carry-on suitcase would cause such a fuss?!

Well, in all honesty, I 100% blame my handsome significant other. As someone who’s on a plane regularly, he has always been a carry-on fella (which is actually surprising considering he’s 6’4 & his clothes and shoes are much larger than the average person!!), and since a lot of my traveling is with him, I have had to learn how to adapt (#compromise?!)…and by that I mean “Not be the asshole girlfriend who checks a bag and keeps everyone waiting.” With all that said, learning to become a carry-on boss babe has been a challenge, but thankfully, I have finally become quite the expert! Last week, in a random instastory moment from the airport at the beginning of an 8-day trip, I shared that I packed everything into a carry-on suitcase, & boy oh boy, was I overwhelmed with yall’s response! I immediately knew I had to make it a “thing,” and therefore, the #KERRentlyTravelingCarryOnChallenge hashtag was conceived!

In light of keeping this post from turning into a full on, carry-on novel, I’ve chosen to break down the outfits/screenshots/items I packed in 2 ways: First up, I will share the exact screenshots of how I planned my looks when I was packing, and second, I will discuss the specifics of the “all star items” and why they were essential & strategic for my #KERRentlyTravelingCarryOnChallenge!

When it comes to packing like this, planning ahead is the best thing you can do. Here are a few of my steps that are crucial in the planning process:

  1. Begin with writing out every day/night that I would need an outfit for. I phrased it Day/Night because I knew most days would be casual and we would get a little snazzier for dinner (aka sneakers by day and heels by night!)
  2. Coordinate by color. Figure out a color scheme that ties everything in your suitcase together. For me on this particular trip, it was my crossbody handbag that I carried with everything. I chose a nude & black bag so LITERALLY EVERYTHING needed to coordinate with it, from my belt, to shoes, to blouses, to jeans, etc.
  3. I wrote down the outfits that I was 100% on. For example, I knew I wanted to take a dress for Napa. I knew what I wanted to wear during the day on Tuesday for the conference. I knew my travel outfit (FYI I always wear the same travel look coming and going!). I knew my blazer was definitely coming. I knew I wanted to wear my glitter top I got on sale at Nordstrom Rack in Vegas one night. So I filled in all those “sure thing” looks first and laid out all those items.
  4. Next is where it gets fun. Once I knew what was already going in my suitcase (GG sneakers, Levi’s, Nude Heels, Black Flare Jeans, etc), I began adding filler items around it: 2-3 more tops to wear with flare jeans, tops to wear under blazer, etc.
  5. I made sure that almost every outfit could be worn with any of the shoes I wanted to take (Nude Heels and Animal Print Heels and sneakers).
  6. Added classics & just-in-case extras like another pair of denim, white button down, and solid tops/tees that could be worn with all bottoms.
  7. Cross-reference back to your day/night list and make sure you’ve got enough pieces (plus about 2 extra JUST IN CASE!)

Black Blazer (with removable dickey inserts): Everything you need to know about this blazer was summed up IN THIS BLOG POST HERE. I can’t say enough great things about why I love it…I mean, the proof is in the pictures: I WEAR THE HELL OUT OF IT, & although it’s a little pricey, it’s paid for itself by how much mileage it’s gotten! 

High-waisted, Distressed Boyfriend Jeans: Its like it’s almost too obvious, BUT I TRULY LOVE THESE JEANS SO MUCH. Aside from being perfectly high-waisted and fitted, but also boyfriend-ish, this pair of denim is easy to wear casually or pair with heels. They are effortless, great fitting, and a no brainer to me. 

Long-Sleeve White Tee: I actually purchased this tee on a whim from Bandier several months back and won’t take it off! It’s a perfect slinky tee material, not see through at all, and has held up after tons of trips through the washing machine. During this particular trip, I wore it on the airplane, with my leopard skirt, and also when I was humming around in the hotel room. 

Black Flare Jeans: If you are a girl who was in high school and collage from around 1996-2008, then you undoubtedly owned a pair of black, “going out” pants. Well, consider these your updated pair. First of all, I love a flare jean for multiple reasons…not only are the CHIC, CHIC, CHIC (just ask Rachel Zoe!), but they are so incredibly slimming on ANY BODY TYPE. I also love how these jeans don’t actually look like jeans and that I can make them look like they belong to a suit by adding my black blazer! 

White Button Down: Regardless of where I am going, what I am doing, & the weather, I ALWAYS PACK a white button down blouse. I can’t tell you how many times I’ve reached for it because it’s always classic, chic, and looks pulled together. You can wear it with pretty much anything on bottom, pair with sneakers or heels, or even use as a coverup if you are at the beach! 

Nude Heels: If you don’t own a pair of nude heels, quite frankly, WHY THE HELL NOT? Aside from coordinating with LITERALLY EVERYTHING (seriously, I could’ve managed without the animal print heels and just taken the nude!), they make every girl’s legs look MILES LONG. 

GG Sneakers: You can guarantee that if I’m not barefoot or in a pair of heels, these are my shoe of choice. They are another item that are on the pricey side, which is why I know they are worth the money….BECAUSE I WEAR THEM A TON. In my opinion, they are a travel essential. Read the blog post I wrote about why they are worth the money (and where to find them on sale!) HERE

Skirt that can be worn with sneakers or heels: I’ve pretty much accepted the fact that I am a jeans girl through and through, but from time to time, I get on a skirt kick! Although this exact leopard skirt is old, I do love the length of it and how it can be worn many ways! When packing, I’ve learned to toss in a skirt *just in case* because you never know where your travels might take you and you’ll glad to have another option other than denim!

I am truly so happy that y’all enjoyed this impromptu, last minute series on my instastories and that I can share the content here on the blog, too! When it comes to traveling, what other content would you like me to discuss further?!

  • Stephanie Balvin

    Can you please share details for the sunglasses you were wearing in your Insta story at Mon Ami Gabi?

  • Allison Quinton

    This is amazing! But almost just as important is how did you get all your hair products and make up in a carry on?!

    • Nicole

      How do you keep clothes looking and smelling fresh after you’ve worn them once but plan to wear again?

      Also wondering the same question above – how did you pack toiletries and hair products/tools? That’s always my biggest struggle!

    • Christina

      Yes! Liquids – please explain this to us. I can’t figure out how you get even the moisturizer on the plane.

    • Hayli

      Yes! Would love a youtube video on getting all of this IN your bag!

    • ASHLEY

      This is exactly what I was wondering. I can make the clothes work but I feel like my toiletries sometimes need their own carryon.

  • Docdivatraveller

    I can’t imagine traveling with just a carry on! I just can’t pack light 😔

  • DC

    How do you maintain freshness/cleanliness for your re-wear items?

  • Karin

    Toiletries and beauty….I need another run down of what you’d take for a week long trip in a carry on!

  • Kari Wallace

    Courtney I workout on vacay and how do you pack that too??

  • Stephanie

    Can you link to the bag you used to hold all of your clothing? I’m looking at carry on bag options now and need inspo.

  • Megan

    Thanks for the awesome insight! Can you also link the carry-on you use? Trying to find a new one. Thanks

  • Terra Scholz

    Show us how you packed all this. lol. Dare you!

  • Lisa

    Love the outfits, especially the white shirt on the far right of the pics you posted at the top of the page. Where can I find that adorable top?? Thanks

  • KB

    I want to see how you packed your suitcase! Do you roll your clothes?!!

  • Kelli McDonald

    Awesome info! What did you do with beauty/hair products?

  • Sl

    I’m with KB. Can you disclose your secret packing tips for carryon only? Going to Charleston would love to roll carryon only!