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How To Pack For A Two Week Trip In One Carry-On Suitcase

There are two types of people in this world: Those who can pack for a two-week trip in one carry-on suitcase, and those who truly believe it’s impossible for them and check their luggage every single time, without fail. I am firmly in the former group, and I am passionate about it. Sure, I can also admit that my deep, deep fear of my bag getting lost on every trip is probably just a little irrational, but still… something about traveling with less just feels better, less stressful. But I wasn’t always this way. In fact, I used to be the person who would bring 10 pairs of shoes on a trip and then wear two of them. But honestly? It’s just not worth it, and take it from someone who has been an over-packer and a carry-on apologist: No matter how much or little you pack on a trip, you will always get to the night before your flight home, look at your suitcase and all your stuff waiting to be packed into it again, and think, “Ugh, I wish I packed less.” Every time.

If you want to do your future self a favor and pack less, the first key is simply just doing it. Tell yourself you’re going to and then just do it. It may take a couple days to get the carry-on just right, but if I, the person who once packed 10 pairs of sunglasses for a one week beach vacation, can do it — so can you. Here are some of the tips, tricks, and rules I live by whenever I pack for vacation now, whether it’s three days or three weeks. Sometimes (well, most times) I have to re-configure my packing situation before I get things just right, but it always works out in the end. I’ve gotten a lot of questions about how I do this, so I thought I’d share my packing knowledge. Here we go.

Buy Packing Cubes ASAP & Use Them To Schedule Your Outfits

I live and die by these packing cubes. Not only do they make everything more compact (and therefore make room for more things in your suitcase), but they make organizing your luggage (and your trip in general) a breeze. For me, the biggest stress with a carry-on (or any suitcase) is re-packing it once you’ve taken clothes out. This is particularly stressful if you’re going on a trip with multiple hotels or stops where you have to unpack and re-pack your suitcase often. My solution? Divide your packing cubes by days, or legs of your trip.

Example: My family and I go on a lot of cruises, which almost always means that the 1-2 days (or more if we’re somewhere like Europe) before the cruise are spent in a port city. Because of this, I always pack the second to smallest packing cube with just clothing for that leg of the trip — underwear, pajamas, outfit, etc. This way I don’t even have to unpack any of the other packing cubes. Everything stays in its correct place, and I already know what I’m going to wear.

I also always make sure I put all my undergarments in one small packing cube, which helps me avoid digging to the bottom of my suitcase for one pair of underwear.

Roll All Your Clothes — Well, Almost All Of Them

The thing about rolling your clothes to avoid wrinkles and make more room in your suitcase? It’s real. Do this in combination with the packing cubes, and you’ll be golden. But it doesn’t work for everything. Have you ever tried to roll a pair of stiff denim or a jacquard skirt? It doesn’t work. You end up with a literal log of fabric the size of a tree trunk. When it comes to thicker fabrics, fold them as few times as possible and place them under the packing cubes. The idea is that folding them only once or twice will keep them thin enough that they only take up a thin layer at the bottom of your suitcase. And speaking of denim…

Never Pack More Than One Pair Of Jeans. Ever.

I don’t care who you are. No one needs more than one pair of jeans on a trip. Absolutely no one. Jeans are one of the items that can be worn again and again without needing a thorough wash, making them ideal for bringing on a long trip — but that also means that you probably only need to bring one pair. If you’re going to bring denim at all (and I honestly suggest avoiding it unless you absolutely cannot), stick to one pair you know is comfortable. And if you’re on the fence about bringing denim at all, think of it this way: You can pack four or five cotton dresses and they’ll take up the same amount of room as one pair of jeans.

Organize Your Personal Item Like A Finely Tuned Machine

I like to consider myself a master of the personal item, AKA that bag you’re allowed to bring on a plane in addition to your roll-on suitcase. In truth, the personal item is how I really make a carry-on go the distance for me. First thing’s first: You need a personal item with compartments. I’ve been using this Calpak duffle bag for the last few months (full disclosure: was gifted to me by the company — if you follow me on Instagram you probably remember me freaking out about it) and it has brought my travel game to the next level. Unsure just how to make a personal item work for you? Here are some tips:

  • Always make sure you put one pair of lightweight shoes in there somewhere. // This is another reason why I love the Calpak duffle bag — it has a compartment at the bottom for a pair of shoes. If you don’t have a bag with a compartment, though, try storing an extra pair of sandals in a thin canvas tote bag (if you’re like me you probably have 200 of these lying in a closet somewhere). Bonus hack: When you get to your destination and unpack, use that same canvas bag for dirty clothes.
  • … or a packing cube. // If you’re going on a trip that’s on the longer side, I suggest ditching the extra pair of sandals or shoes and instead packing a small packing cube in your personal item with all the clothes you’ll need for the first couple days of your trip.
  • Only pack the things you’ll actually use on the plane. // OK, this sounds simple, but someone needed to read it: You don’t need four books in your carry-on if you know you’re going to watch a movie the whole time. You don’t need your laptop “just in case you get a work email” on vacation. You don’t need an iPad if you can use your phone for the same tasks.
  • … except for toiletries. // If you, like me, are prone to panic and anxiety about things like forgetting to pack contacts or a pair of glasses, then please heed this one piece of advice: Put them in your personal item. If I need to double-check that I packed something, I simply glance in my personal item instead of wondering if I should dig it out from the middle of my suitcase. This keeps things as stress-free as possible. Plus, it makes it that much easier to take them out in security and breeze through the line.
  • Always leave room for a cross-body purse or fanny pack. // I added fanny pack because, hey, fanny packs are cool now, right? Maybe? OK moving on. This hack is simple enough, but it is my saving grace. I always make sure my cross body purse (this Dagne Dover bag has been my go-to for a while now and is perfect for travel and everyday wear) can fit in my personal item — even if just barely. This means I have the ease of being able to get to my phone, tickets, ID, and wallet as quickly as possible throughout security and walking through the airport without having to dig them out of my personal item. It also makes it easy to divide out the things I really want to use in the plane. In addition to things like my passport or wallet, I also always keep my charger, headphones, medicines (Advil, etc.), and an extra pair of contacts in my cross-body purse so that I can just reach down and get any of them mid-flight instead of pulling out my whole personal item from under the seat in what is usually a cramped space.

Eliminate As Many Toiletries As You Can

Many people I know from working in the beauty industry (or, well, beauty industry-adjacent) in the past have told me that they won’t bring a carry-on because they need their full size skin care products. While I can’t really help anyone who is stuck on this, there is always the option of buying smaller versions of those products that you can travel with, or transferring the product into smaller containers. For me, I keep it simple when I travel: Makeup removal wipes, cleanser, toner (I find that Pixi’s Glow Tonic usually is the best for me during travel, plus it comes in a easy-to-find travel size bottle), moisturizer. That’s it. If you do want to bring more skin care, though, consider all the ways you can pack less liquids altogether: Use toothpaste tablets instead of a travel-size tube, try out a stick cleanser, or use makeup removal wipes instead of micellar water (my go-to move to save room). And remember: You probably aren’t going to use that mini hair spray or mousse or shaving gel nearly as much as you think you will, so toss it and save yourself the room now.

Be Strategic About Makeup

Look, I like beauty as much as the next person. I, too, still have a part of me that really goes into every trip believing that I will do a full face of makeup at every fancy dinner and cocktail bar I visit. But, at least for me, that rarely happens. I now am pretty strict with myself when it comes to what makeup I bring. However, I do find that packing the below only gives me options to experiment with beauty without packing 900 palettes. In addition to packing my everyday, go-to beauty products (I wrote all about them here), I’ll bring a Huda Beauty mini shadow palette, a red matte lipstick (this Nudestix one is a favorite lately, and can also be used as blush), a Pat McGrath lip gloss (holy grail gloss), and maybe one pair of fake lashes if I know I’ll be going out one night. It’s only four items, but provides enough variety that I don’t feel like I have to do my makeup the exact same way every night.

Pack Dryer Sheets In Your Suitcase

If you’re going on a long trip, you may be worried that stuff will start to smell a little funky after a while (especially if you’re stopping at multiple locations and have to pack and re-pack your bag). Make sure you line your suitcase with dryer sheets when you pack and everything will be smelling as fresh as possible. Put extras of them in whatever dirty clothes bag you’re using. I’ve also put them in shoes before, which has worked wonders.

Make Sure You Can Get At Least Two Looks Out Of Every Item Of Clothing

I usually plan about 60% of my outfits when I pack for any trip, while still leaving room for mix-and-matching and a wild card here and there. And I almost always end up with clothing to spare at the end of the trip. My point is: You don’t need as many clothes as you think you do. Period. The key here is really bringing pieces that can be dressed up or down. On a recent trip to Europe I wore this red silk skirt with a white T-shirt and Birkenstocks, and then again to dinner with an off-the-shoulder wrap top and layered necklaces for something a little more dressed up. I wore a floor-length peasant dress to explore during the day and then paired with espadrilles t night. If you’re thoughtful about how looks can transition when you pack, then it’ll be easier to get dressed day-to-day.

Never, EVER Pack Things You’ve Never Worn

If there is something in your closet that you haven’t worn despite the fact that you’ve owned it for more than a year, I don’t care what it is (looking at you, random pairs of sunglasses and headbands and bathing suits that are collecting dust on shelves across the country) or how great you feel about it, do not pack it. If you’ve owned an item for a long time and haven’t worn it yet, you will not wear it on your trip. Trust me. All you will do is take up valuable space that you should use for something else.

Remember: No Trip Requires More Than Three Pairs Of Shoes

Unless you are participating in a different type of physical activity each day or attending a gala each night, there is no reason in the world to pack more than three pairs of shoes (and one wildcard if you can fit it in your personal item). This means you wear one on the plane and pack two in your roll-on suitcase. Easy enough, especially if they’re flat sandals. I broke down my usual choices below based on general trip locations, if helpful:

Beach/tropical/summer trip: Birkenstocks, “nice” flat sandals (I have worn these gold Loeffler Randall sandals probably close to 1,000 times over the past three years and they are my go-to sandal for going from day to night), rubber flip flops for pool/beach. Wildcard: Running shoes for working out OR heeled sandal.

Europe/walking/exploring trip: Birkenstocks, “nice” flat sandals, white Adidas Stan Smiths. Wildcard: Running shoes for working out OR heels.

Cold weather trip: White Adidas Stan Smiths, heeled booties, flat boots for walking. Wildcard: Running shoes for working OR soft over-the-knee boots (easy to fold for packing).

I would say for most of the trips I’ve been on until this past year, I’ve brought more shoes than this for one reason or another, and here’s the thing: I never wear them. I always end up going back to these 3-4 options.

All of these tips and tricks help me pack as light as possible, but the whole process is also very much about being patient and willing to put stuff aside and reconfigure things. If you’re not willing to angrily beat on your suitcase and bitterly throw aside a pair of stilettos you know you’ll never actually wear in order to make room, then the whole process probably won’t work for you. If you’re willing to stick it out, though, it’s worth it. And in my experience? Once you commit to only ever using a carry-on, there’s no going back.

  1. Momma

    November 1st, 2019 at 12:56 pm

    I think the 4 book comment was directed at moi! 😊

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