Definitive guide to packing carry-on like a boss

Photo credit: Robert Couse-Baker

My day job has me living out of a suitcase Monday – Thursday of most weeks, with some weekend personal travel as well (ex: I recently returned from a 3-week trip that had me in Charlotte, Atlanta, Seattle, San Francisco, Monterey, Los Angeles, and Phoenix), so learning how to actually pack for a trip is one of the most useful life lessons I’ve picked up over the past two years.

Rule 1 of air travel in the modern age: do it in carry-on

Beyond checked baggage fees and the time to check and retrieve luggage (painful), traveling in carry-on is ridiculously practical because it means you actually have your stuff in the event of flight delays, cancellations, and/or flight changes. The most stressful trips I’ve taken as of late are the ones in which I checked a bag and then ended up moving flights during an itinerary with connections…so while things worked out surprisingly well, the “Will I have clothes for tomorrow?” game really isn’t much fun.

So. Carry-on. 

Within the US, that means you have 45 linear inches (or 114 cm) in combined length, width and height (including any handles and wheels) that you can fill, which, for me, means two work weeks + a weekend trip out of a suitcase if I’m not planning to do laundry. Give me access to a washing machine and similar weather at all places I’m going and that can jump to 3+ weeks. All in carry-on. 

Example time: here’s what was in my bag for a 9-day trip that featured 2 travel days, 4 days in Switzerland, and 3 work days in Charlotte, NC:
Plus a few things not pictured (undergarments, workout gear).

For my day & evening clothing (for both casual time and work), this breaks down into:
  • 2 wrinkle-resistant dresses
  • 1 pair of jeans
  • 1 button down shirt
  • 1 flowy black tank (wore on plane)
  • 1 blazer
  • 1 skirt
  • 2 scarves (wore one on plane)
  • 1 belt
  • 1 pair of dressy flats
  • 1 pair of knee boots (wore on plane)
This may not sound like a lot of stuff, but I can assure you that it's more than enough for the time I was on the road. Here's what I wore for work and play over the course of 9 days (with a few extra options thrown in and excluding hiking clothes):
As you can tell, lots of mixing, matching, and wearing things in ways you wouldn't expect. One of my favorite tricks, for example, is wearing things over dresses, like the cranberry skirt over a black dress (above). Dress tricks aside, here's how to play with a few pieces to make a fresh outfit each day:
  • Choose a color family and stick to it. For this trip, I'm going with cranberry as my accent color and then playing with patterns and textures with my neutrals (black, cognac, taupe) to make the rest of my outfits interesting
  • Plan potential outfits out ahead of time. This will help you determine if you can leave something at home (ex: If I weren’t going somewhere with cooler weather, I’d consider leaving my jeans behind because they’re only used once here) or if you need to add a few more things to get you through your trip
  • Scarves and belts can work wonders for making something feel like a new outfit while taking up minimal space in your suitcase. Bonus for scarves: they double as blankets on airplanes
  • Don't be afraid to re-wear things. If you're mindful about taking care of your clothing, you won't need to wash it nearly as much as you think you do. Besides making packing for travel a breeze, wearing clothes multiple times before washing (so long as they're still "clean" and odor free) will help them last longer too 
  • Wear things in unexpected ways. Beyond the “skirt over a dress” trick, you can also rock a turtleneck or a sweater over a dress, that, when belted, looks like a top and skirt (and something completely different than the dress you wore a few days prior)
  • Be mindful about shoes. Bring shoes you've broken in (nothing can ruin a trip quite like a blister) AND will actually wear. My go-tos for work/pleasure combo trips are 1-2 pairs of something dressy, 1 pair of cute and comfy shoes for running around town (ex: sandals or riding boots depending on the season), 1 pair of running shoes, and my Birkenstocks.
    Typically, I’ll wear the Birkenstocks for commuting (happy feet + great for TSA + saves my work shoes for the office), have 1-2 pairs of heels in my bag, and have my other shoes tucked in the base of my bag. I obviously don’t bring 4 pairs of shoes with me all the time – usually it’s something like 1 pair of work shoes, running shoes, and then my Birkenstocks – but this will completely depend on where I’m going and the season. In the winter, Birkenstocks are swapped for short winter boots if I’m going anywhere chilly (ex: Chicago), and if I’m just traveling for work, I’ll leave my more casual shoes at home. Long shoe story short, it’s all about being strategic and keeping your feet happy.
  • Little known secret for making everything fit: roll your clothes. Rolling takes up less space than folding and it helps to keep your clothes wrinkle free. Again, here's how much I'm putting in my suitcase:

And here's how it looks when rolled:
My wallet, watch, and passport are included here for perspective
to show just how small all of this rolls up to be - it's pretty incredible.

Now for the foundation of everything: the suitcase.

The Suitcase

The start of any good trip is a good carry-on. There are lots of brands out there at lots of different price points, but at the end of the day, your bag should feel good in your hand, be within carry-on size restrictions, have the features you're looking for, and be within your budget.

As for me, I wanted something that was well made but under $200, looked both professional and a little different so that I could pick it out of the sea of black bags if it had to be checked, had a separate shoe compartment (which is also great for dirty laundry at the end of the week), and was easily organizable.

What I use is nothing fancy (a super sturdy REI bag), but it fit everything on my wishlist, has handles in all of the right places, is shaped to fit on any plane (including regional jets), and still looks great after two years on the road.

The last key for a suitcase is to have an ID tag or some other decoration that makes it really easy for you to identify it if you do have to check it (gate check or checking pre-security). Some people use ribbon, others use tags – it’s completely up to you and is a fun way to add a touch of personality to a standard black bag.

Now for the fun part: actually packing your bag.

The following is my process - it'll be a bit different based on your bag, but the premise for how you pack it is the same. Same thing goes for you, gentleman, look at the methodology versus the actual verbage.

1. Lingerie goes into one of the mesh pockets (I love that it's zipped so if my bag is opened in public, the embarrassment factor is pretty much zero; my jump rope and interval timer go into the other
2. Running shoes go at the bottom of the bag. The goal is to build a study base as well as to put the heavy things at the bottom of the bag so that when you stand it upright, you don't crush the delicate things
3. The second pair of shoes goes next to the running shoes. If there is still space, my straightener will go in the middle. Note: odor balls and/or freshener packets do wonders for keeping your shoes (and therefore your bag) stink-free. I never travel without them in my shoes.
4. After I have my shoes in, I take a plastic bag (usually one of the laundry bags I get from hotels) and put it over my shoes as a barrier between them and my clothes. From there, clothes go on top.
5. Voila! I'm planning to wear the boots on the plane (along with yoga pants, a long, blousey shirt, a jacket, and a scarf), so aside from the boots and scarf, everything on my list is in the bag. As you can see, I have extra space, which, after I add my workout clothes, non-liquid toiletries (a small cosmetics kit) & emergency kit (lady products, band aids, etc.), I'll fill based on the trip needs.
For work-only trips, I'll use the extra space for another pair of heels or (more commonly), for snacks for the week:
Side tip: Carrying healthy snacks = the best way to stop “hangry” if you’re traveling or working unpredictable hours. Sliced carrots, roasted almonds, dried sour cherries, roasted soybeans, killer dark chocolate, and whatever leftovers I have from cooking over the weekend are my faves.

For this trip, I filled the rest of my suitcase up with workout/hiking gear, layers, and other necessities:
  • 1 casual shirt (will double as a pajama top) 
  • 2 pairs of sandals (1 pair of shower flip flops for the hostel, 1 pair of Birkenstocks) 
  • 7 pairs of socks (6 running, 2 wool) 
  • 3 bras (2 nice, 1 sports bra) 
  • 9 pairs of underwear 
  • 1 pair of yoga pants (wore on the plane, can double as an extra layer if cold) 
  • 2 pairs of running tights (1 doubling as pajama pants) 
  • 2 running tops 
  • 1 long sleeve technical shirt 
  • 1 running hat 
  • 1 fleece jacket (wore on plane) 
  • 1 raincoat 
  • 1 blender bottle & protein powder 
  • 1 bag of roasted almonds
One thing to be mindful of while packing your carry-on – just because it zips doesn’t mean it’ll fit on the plane. If you’re flying on regional jets (trips under 1000 miles in the US), chances are the overhead compartments are smaller than what they’d be on larger planes (A320s, A330s, 737s, 757s, etc.) used for longer or more popular flights. If your suitcase is expandable, aim to fly with the expander closed.

The sneakiest trick for taking everything you want if your suitcase is a little stuffed is to wear the bulky stuff. If I tried to pack the fleece jacket I brought, for example, I would have had to have left the rest of my workout gear at home. By wearing it and the boots, however (along with yoga pants and a blousey shirt that would roll to be really small within my suitcase for the rest of the trip), I was able to fit everything I needed. If I'm traveling for work, this means I'll wear a blazer instead of packing it, or, if I'm bringing two, will wear one and pack one versus packing both.

If you’re still looking for space, take a hard look at what you’re bringing to determine 
a. If you really need it
b. If you can borrow it where you are going (ex: blow dryer)
c. If you can afford to buy it there 

Being able to travel in carry-on > 1 extra pair of heels, your own blow drier, or more than 1 pair of jeans, so while leaving it may be scary, it’ll be worth it.

Post-trip verdict from this packing job? Pretty dead on. I used everything except for the wool socks, never wished that I had something that I didn’t bring, and my bag fit on all 6 planes I took. All in all, I’d call that a packing win!

What tips / tricks do you use for travel?