By: Alexa Rys, The Dot Ambassador
If you’re like me, you love to travel – especially when it means getting out of the office (whatever your office looks like these days). Balancing being a go-getter in my corporate job and taking much needed time for myself has not always been easy. However, through personal experience and good ol’ trial and error, I have learned some very valuable tips & tricks that have helped me fine tune the art of being ~out of office,~ whether that’s the personal or work related prep that taking PTO requires, travel hacks along the way or getting back into a routine upon your return. And – I will be sharing them with you through our next multi-part Coffee Talk called “The Out of Office Series” starting first with this week’s post: ‘Trouble Packing for a Trip? Carry On.’

Do you travel for work? Visit friends and family out of state? Are you planning for a longer summer vacation? Maybe a bachelorette party or honeymoon? No matter what kind of travel you find yourself doing, there are always going to be the ‘uncontrollables’ – the factors you cannot account for no matter how well you plan: flight delays, crew running out of hours, weather, etc. However, there is one factor purely within your control that can make the difference between a successful & unsuccessful trip – how and what you pack.

In chatting with friends, I often find that ‘how’ you pack is shaped by those you first traveled with. For me personally, we were a ‘checked’ family, meaning when we flew, our bags were going to be out of sight in the belly of the plane until we optimistically waited at the baggage carousel with hopes they successfully made the trek with us unscathed. However, as I had the opportunity to travel more independently beginning in my high school and college years, I quickly learned there are so many cases to be made for why travel by carry-on is the way to go – a few of the most significant perks being:

• Save money by avoiding check baggage fees (pending airline/status)
• Save time by avoiding check baggage lines on departure and baggage claim on arrival
• Access to your items at all times throughout your travel day
• Remove risk of airline losing your baggage
• Ease of travel in non-US cities (transportation and accommodation in cities outside of the US are not always accommodating to traveling with larger luggage; think cobblestone streets, no elevators, public transit, etc.)

Through experience, I found the pros of traveling by carry-on to far outweigh any cons and never. looked. back. For the last 5+ years, I have only traveled by carry-on. You read that right – whether it was a 2 day trip for work, 10 day honeymoon to Europe, 14 day family trip to the Caribbean or a month long backpacking adventure across Asia, everything I bring is packed between my 2 carry-on items: the overhead carry-on and the under seat personal item. Even for a maximalist like me that loves a good ‘fit’ complete with accessories from head to toe, I can confirm that it is possible.

If you are a consistent ‘check-er’ when traveling by plane, you may be asking yourself ‘HOW?!’ especially when it comes to trips lasting longer than a few days – and you’re not alone. When I went on my most recent trip and posted an Instagram story about only traveling by carry-on and sharing what I brought, my inbox quickly filled with reactions from friends and family who were eager to understand how it was possible:

These responses led me to brainstorm the tips and tricks I have developed through trial and error over the years that allow for the most optimized, and I mean OPTIMIZED, approach to traveling only by carry-on – and I want to share with you!

If you are interested in traveling more efficiently and becoming a newly crowned ~Carry-On Queen~, these are for you:

Outline Your Trip

In order to set yourself up for success when packing, ask yourself the following questions to help determine both the type and amount of outfits you will need to pack:

• What is the purpose of your trip – work, family, vacation?
• How many days and nights do you need outfits?
• What will the weather be like? Can you plan on one temperature range or do you need to be prepared for multiple?
• What activities will you be doing?

Plan Your Outfits Proactively

Have you ever packed an item for a trip that you never wear at home in case you suddenly felt like wearing it on your trip? Or 3x the amount of pants you could ever go through in the amount of time you are traveling? That type of packing approach can often be enabled when using a large checked bag because you have the space but will NOT work when traveling only by carry-on – and that’s a good thing! Nothing should be coming with you, ultimately taking up space, that doesn’t or couldn’t have a likely purpose.

• Take into account the questions you answered when outlining your trip
• Pack outfits using ‘capsule’ items – tops and bottoms that could be mixed and matched for numerous outfits to help you get more use out of the items taking up precious space in your carry-on bag, especially for longer trips
• Document the outfits you put together while planning. You could 1) write out all items that go together in a note on your phone, 2) take a photo of the complete outfit, 3) physically try on each outfit and snap a photo to keep for reference in an album on your phone – or some combination of these options. I personally, like to physically try on all outfits to make sure I feel good in them and like the way they came together so there are no surprises when I arrive to my destination – higher likelihood I will actually where everything I brought! I also like having visual documentation so that when I am deciding what to wear each day, I have a quick reference of my options.
• Take note of duplicative outfits and remove. Once I have documented each outfit and feel confident my choices are appropriate for the travel I am doing (again, keeping in mind the outline questions), I review if there are any outfits that serve a duplicative purpose or if I have too many outfits for the days/nights I need and remove. If you are going to an elevated dinner one night on your trip but pulled 3 cocktail dresses, 2 can be removed from packing consideration to make room for other fun outfits!

If you only take one tip away from this blog post, let it be to plan your outfits intentionally and proactively.

If you only take one tip away . . . let it be to plan your outfits intentionally and proactively.

Example from my most recent trip to the French West Indies | 14 days, warm climate, combination of swim, casual day and more formal night outfits a lot of outfits here but many more created by mixing and matching!

Evaluate Your Luggage

If you are bringing only a backpack as your overheard carry-on and a small shoulder bag as your under seat personal item, the carry-on only packing approach will probably be out of reach – you’re leaving allowed carry-on space on the table!

• Use baggage that allows you to use as much carry-on space as possible within airline limits. For most major airlines the carry-on size restrictions are as follows:
  • Combined length + width + height must not exceed 45 linear inches
  • Individual length, width and height measurements may not exceed 22” x 14” x 9” respectively
• Choose bags with a flexible structure. Bags with super rigid structure prevent you from really making the most of your carry-on space while bags with more flexible structure give you a bit more leniency.
• Make sure you are capable and comfortable transporting your own baggage. Knowing you will be transporting your baggage yourself vs checking, make sure that you are using baggage that makes transportation as efficient as possible. I like to use an overhead bin carry-on that rolls and an under seat personal item that attaches easily to my overhead bin roller.
• What luggage do I use? (p.s. this is not a paid endorsement)
  • Overhead Bin Carry-On: The Bigger Carry-On (Away Travel)
    • Recommended Features: largest size roller bag that can be carried on for most major airlines, lightweight enough for me to lift into the overhead bin myself, 360 degree spinning wheels for convenient rolling, durable hard shell that still has some givePlenty of brands offer options with similar perks – look for an option that optimizes the carry-on room you are allowed and rolls well!
  • Under Seat Personal Item: Landon Carryall Bag – Large (Dagne Dover)
    • Recommended Features: largest size duffle bag that can be carried on under the seat for most airlines, good give for flexible packing, right amount of pockets in the right places for what I need, exterior sleeve to slide onto my roller bag handle
  • In addition to the overhead bin and under seat personal item, you also get a ‘Free Item’ to carry-on. This could be a jacket or an item you purchased past the security checkpoint but for me, this is often a stiffer brim hat that I choose to carry with me on the plane to avoid damage. To help me easily transport my hats, I use a hat holder (a magnetic hat clip) from the company TOPTOTE that hooks directly on my bags and allows me to carry my hat hands-free. If you are a ‘hat-girl’ as well, I would definitely recommend!

Pack your ‘Over’ vs. ‘Under’ Carry-On Items Strategically

Although you’re carrying-on, you still get 2 decent size bags to pack in. Be intentional about which items go in which bag – the overhead carry-on and the under seat personal item.

• Overhead Carry-On: This bag should be used to pack as many items as possible that you will not need until you arrive at your destination. Think of it as your ‘checked’ bag without the hassle of a checked bag. Pack this bag full first before you look to pack any non-necessary items in your under seat personal item. This bag will end up being heavier of the two which you won’t mind because there is no weight limit for carry-on baggage and you chose the right bag to make transporting it around the airport so slick
• Under Seat Personal Item: This bag should be used for items that you will or could need throughout your travel day. Think essentials like your ID/Passport in additional to other items like: headphones, gum, chapstick, snacks, hand sanitizer, laptop/ipad, book, sleep mask, skincare, makeup, etc. Prioritizing only necessary items in this bag allows you room to pick-up a treat at the airport or a new book without feeling stuffed to the brim. It also means more room for your feet under your seat

Utilize Your Space

When you are working with only carry-on baggage, you do not have an abundance of space to work with, so be strategic about utilizing the space you do have – both inside and outside of your baggage.

• Wear your bulkier items on the plane. Bringing a chunkier cardigan or sweatshirt? Wear on the plane! Bringing tennis shoes or boots? Wear on the plane! Not only are you probably more comfortable/warmer on the plane when wearing these items, you’re also not taking up a disproportionate amount of space in your baggage with bulkier items.
• Pack items inside of other items. My family jokingly calls my baggage the ‘clown-car carry-on’ and this is why. Packing a pair of shoes or a handbag? Put a few pairs of sunglasses or other small accessories (jewelry, hair clips, etc.) inside of them. Not only does it keep more fragile items protected while traveling, it also allows you to bring more items by utilizing what would otherwise be dead packing space.

Rolling is Your BFF

I’m telling you – you’ll surprise yourself with how much you can fit. 

• Unless an item truly cannot bend, like a shoe or a hair tool, it should be rolled. Rolling items optimizes your space and allows you to get far more items in your bag than simply folding – I personally compared both methods a few years back and can confirm this to be true

• Packing cubes? This is likely a controversial take compared to any other packing tips you will find online BUT I am team no-packing cubes in most situations. Although I love the concept of having like items packed together for the sake of organization, I have found that the structure of packing cubes often takes up more space than I am willing to part with. I see more value in packing cubes during longer trips when you are bringing more items to keep organized however that is also when I want to completely optimize every inch of space I have to account for more days. As a result, I’d rather have a few extra items vs having all shirts in the same pouch.
• Once you are all packed, take a photo of your bags. If traveling only by carry-on is new for you and packing was a challenging puzzle to figure out, I recommend snapping a photo of your bags packed in full to reference when it’s time to pack up to return home. The return packing is never as fun so save yourself from having to remember how you got everything to your destination by using a reference picture!

Unpack When You Arrive

Regardless if you are traveling for 2 nights or 14, unpack your suitcase. Maybe you’re hopping to dinner or an event right when you arrive – go, enjoy – that’s why you’re there! But when you arrive back to your accommodation and have a minute, unpack – the sooner, the better. Why?

• If you have intentionally packed using all other tips listed above, every item you have brought has a purpose, and therefore will be taken out of the suitcase at some point so you may as well do it right away!

• Unpacking not only allows rolled clothes to un-wrinkle, but allows you to see everything you brought, encouraging and reminding you to make use of them.
• If you’re traveling for work with early mornings, feel anxious about looking the part or maybe just traveling to a new place, unpacking allows you to feel more settled in your new home-away-from-home, get your outfits organized – maybe even ironed or steamed – before you need them and overall feel more ready for your trip ahead.

Plus – you’ll now be so impressed with all that you were able to bring by only carry-on, you’ll want to revel in your accomplishment!

Example from my most recent trip to the French West Indies | Always fun to see the outfits you created during planning and saved in your reference photo album come to life once you arrive – and know you have the right outfits and options for your trip. The world is your oyster!