How to Overpack In A Carry-On Bag + Best Carry-On Luggage for All Budgets!

If you’ve been following along for a while, you’ll know that I’ve been doing a lot of traveling lately…I’ve been incredibly proud of myself because despite being a lifelong member of ‘Team Overpacking’, in this last year I have officially mastered the art of traveling light…without having to say goodbye to all of my choices!
I’ve taken over 25 weekend trips in the last year, and have managed to bring nothing more than a carry-on bag and my purse every single time (this might seem small to you, but somewhere, my parents are clapping after watching me lug 50+ lb. suitcases on vacations lasting 7 days or less for years!) 
Those of you that love to bring extras, options, and “just-in-case” items might be reading this and thinking that you wouldn’t be able to pull that off…but don’t stop reading just yet! The best part about my newfound packing secrets and travel lifestyle is that I am still able to bring tons of extra options. You just have to pack smarter, not more!
*I will note that the time of year that you are traveling plays a role…summer items are obviously much less bulky than winter items, but it can still be done!*

I’m sharing with you my best secrets and tricks for overpacking in a carry-on bag so that you don’t have to sacrifice that super cute extra top, spare jacket, or adorable vest that is probably too puffy but that you really might need!

1. Choose a Color Palette – I’m not telling you that you need to have a “capsule wardrobe” to pack light…as nice as the idea of those can seem, I personally love how varied and mixed up my closet can be as a whole. That being said, when it comes to packing a bag, one of the smartest ways you can pack is to choose items that work multiple ways. Based on the events, occasions, and weather, I typically choose a basic “color palette” for the weekend. For example, I might choose blues, greys, whites, and other neutrals because they will all go together, but can still be mixed in different ways. Farther down the list, I’ll explain a tip to help keep these similar colors from looking too simliar day to day!

2. Only Make Cutbacks Where You Have To – It’s totally the worst when you pull out all of the items you want to bring, only to realize you’re going to have to say “no” to a large chunk of them. Rather than making a decision on every single item, try to approach it from the smartest way possible. Tackle the bulkiest and most common items first: shoes, purses, and outerwear. Ask yourself questions like these:

  •  Do you have a neutral pair of shoes that will go with multiple outfits? Maybe one that can be dressed up or down? Keep it. 
  • Do you really need more than one pair of dressy shoes? Toss the spare heels. 
  • Need a comfortable walking shoe for the outdoors? Combine it with your “casual shoe”…maybe a pair of converse, or a comfortable sandal that can be worn multiple ways. 
  • If you really want to bring extra bags & clutches, make them useful by storing your jewelry or carry-on items inside of them, and then stuffing them into your tote for the plane.
3. Make Your Accessories Do The Work – The best part about choosing your colors and outfits wisely is that you can still have tons of different looks without taking up extra room in your bag. Utilizing scarves, different jewelry, hats, and layers is a great way to re-use outfit pieces while still having a totally different look. 
4. Keep The Bulkiest Items With You – You’ve probably heard this one before, but keeping your bulkiest items with you the day you travel is a huge space-saver. This one definitely comes in handy during the colder months. My black Frye Boots are one of my favorites, and are so classic that they match everything…but they’re not very flexible for packing. I always end up wearing them on the plane, along with a blanket scarf in my bag and whatever coat I’m bringing with me. Now I get to keep all of those items with me, and not one of them had to make room in my bag!

5. Check the Weather – This one might seem obvious to some, but I can’t even tell you how many friends I have that insist on packing “for all weather”. While I am a huge supporter of being prepared, and weather can still throw curve-balls from time to time, keeping a close eye on weather for the week leading up to the trip can usually give you a good indication of what to expect. Skip out on bringing the raincoat, and pick up a cheap disposable umbrella while you’re away if need be. You don’t need a whole special set of rain boots just in case, either. That’s what cars and umbrellas are for!

I’ve also linked my favorite carry-on luggage bags below…it’s definitely time that I invested a new one sometime very soon! Any suggestions or bags that you really love? I’d love some help choosing! (Bags are shown from most affordable to splurge!)

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Hopefully these tips will help you make smarter, not tougher, decisions on which of your beloved wardrobe items make the cut on your next trip…and you’ll get to pocket those checked baggage fees (and avoid the anxiety of a potentially lost bag) for more fun aspects of your trip!

Safe travels! Does anyone have any fun weekend trips coming up?! I’m trying to plan my dream list for 2017 already…

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  • Reply
    Okwoche Daniel
    October 17, 2016 at 4:39 pm


  • Reply
    Kelly @ North Country Nest
    October 17, 2016 at 4:40 pm

    Such great tips – I loved the one about picking a color palette! I miss actually leaving for a long weekend trip on Wednesday so these will come in handy 🙂

    • Reply
      Olivia Tennant
      October 17, 2016 at 4:59 pm

      The color palette has been a HUGE helper to me (especially since I tend to opt for the same few colors in my closet anyway…) Have so much fun on your trip!

  • Reply
    October 17, 2016 at 5:03 pm

    Very nice read! I will definitely have to try a few of these tips on my next trips to Barcelona & Donostia 😉

    • Reply
      Olivia Tennant
      October 17, 2016 at 5:04 pm

      Thank you! I hope they help – those trips sound amazing! I would love to get back to Barcelona someday soon.

  • Reply
    Erin N
    October 19, 2016 at 1:46 am

    Although I seem to be physically incapable of packing light I will definitely try some of these tips next time I go on a trip! I normally check a very large suitcase, when I'm forced to bring a carry-on I prefer to bring a duffle bag because I find it easier to cram everything inside (vs a hard suitcase).

    • Reply
      Olivia Tennant
      October 19, 2016 at 1:57 am

      You definitely should – they've made a huge difference for me! I'd love to hear how it goes next time you try it! I totally agree on the bag thing…the carry-on I use is actually an old one (which is why it's not linked in this post) but it's a soft duffel-type bag with wheels to make it easier to carry on. I find I can fill it much better with the flexibility of having soft edges (and pushing the limits with creative folding) but I DO get grief from airlines always making me "prove" that it fits within the little guidelines! Thankfully, it does…every time!

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