Carry On — How to Pack for Vacation in a Tiny Bag

Wanna come?


My friend’s mom has been sharing the same self-written axiom with him since the time he was 17, impressionable and beginning to fall in love with all the wrong girls.

“All women have baggage, you’ve just got to pick the ones who travel light.”

For the subsequent ten years, I can confirm that said friend selected only the kind of soul-crushing manic pixie dream girls who do not take lightly — pun intended — a short trip and travel with — never mind one large trunk — multiples.

My father has shared a similar, also self-written, albeit vaguely less articulate axiom with me: “Stuff ruins trips.”

Never did this prove more true than on my honeymoon, which took place in Greece and commanded travel from three different locations that would have been considerably easy to hop to and from by boat, train and air had I felt more…mobile. I learned two lessons on that trip: 1. Santorini is not a town built for heels and if you try to enforce an otherwise mandate, you are a sucker; 2. A sarong — singular — and one bathing suit would have been enough.

I had the opportunity to rectify my wrongs last summer when I went to Croatia with a large backpack that fit in the airplane’s overhead cabin and you know what I learned? That my dad is always right. Stuff ruins trip. Backpacks, however, do not.

But I digress again.

Tomorrow, I leave for Paris, where a bi-annual fashion week is already in progress and for the past three seasons, I have been exhorting the benefits of traveling with a carry-on without actually having shown you precisely what I put in said carry-on so allow this GIF to demonstrate.

Essentially, what I do is lay out four outfits, all of which consist of at least one garment I have worn more than three times in the past month. There’s a striped shirt, a houndstooth jacket, the best vintage Levi’s 501s on the face of this planet and some gold boots to boot. (Note: they double as a toiletry kit for the purpose of packing.) In setting aside these garments, I build outfits around them:

A Bambi-print skirt, which harmed exactly zero deer, would conceivably look great with stripes.

Those Levi’s could use the aid of a navy poplin turtleneck, which I anticipate layering under another white poplin crop top.

What are those boots for if not (first and foremost, ideal travel-wear) an entirely white look punctuated by an ivory tweed Chanel blazer, and where pants may fail me next to a houndstooth blazer you know what never will? Fringe.

So that’s that — four outfits that will rise to the chameleonic occasion, make like a clown car and multiply until either the cows come home or I do.

For now, though, I really ought to go.

Let me, however, leave you with this: never underestimate the power of on-airplane wear. Make that five outfits.

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  • Gablesgirl

    Assume your toiletries are in your beach bag. That’s a hell of a lot of shoes.

    • Leandra Medine

      They are actually INSIDE the shoes!

      • Andrea Raymer

        that is actually the smartest thing I have ever heard.

        • Crazy AboutJCrew

          I agree, never thought of that. I usually stuff them with underwear/socks.

        • Quinn Halman

          I always pack my delicates in my shoes

      • Stacey K

        Aaaand you just taught me how to pack for everything, ever. Life solved.

      • laprairielily

        I used to do that before those jerks at the airport started insisting that everything had to be in a clear plastic bag. I assume they’re too impressed with your beach bag to bother you.

        • Sarah Moore

          Liquids can go in hold luggage. I regularly fly long haul (up to 35 hours) so I hold on to free samples to pack in my clear bag for the flight. Face wipes, moisturiser, LIP BALM (the single most important item for a dry atmosphere), eye drops.

          • laprairielily

            I never check a bag. I travel with only my carry-on and a small purse.

          • Sarah Moore

            Do you never go for longer trips? I generally have a small bag’s worth of clothing, the rest of my case full of presents for my family, and 100ml is not enough conditioner for a four-week trip so there’s generally a good amount of toiletries in there.

            I don’t use a massive bag – we call them “American suitcases” here and you can’t even buy them in the shops – my case is big enough for clothes and presents and small enough to manage public transport on the way to the airport. And my handbag with me on the plane – how do you cope without a handbag?

          • laprairielily

            I don’t judge anyone for carrying more, but I’m a minimalist and airlines lost my baggage so many times when I was a kid that I don’t trust them anymore. My “small purse” is more of a handbag, though.

      • pamb

        Aren’t you worried about leakage? Not having toiletries in a plastic bag worries me…

    • GapToothedGirl

      This info is fundamental…I’ll definitely try this with my bag!!

      Thank Leandra!!

      XOX, Gap.

  • Jessica

    This =a great post.

    ‘N I wanna come!

  • Julianna

    Who makes your suitcase? I love it!

    • Leandra Medine

      Bric’s! It’s credited/linked in slideshow caption

  • parkzark

    That suitcase is awesome. It looks so damn durable

  • The shoes are the worst to pack, but I am always about carry on. The bambi print skirt is so cute.

  • Devil Wears Pra-duh

    I LOVE THOSE BOOTS! I’m thinking about getting these ones:|SeasonId=61I&CollectionId=0C9

  • Wow love seeing how much you packed in there!

  • alex

    my Italian friend always says i need good Italian shoes to wear to in Greece. I say no!! Greek streets will tear up any and all shoes. just wear flat sandals the entire time. be prepared to throw them out when you’re trip is over.

    • alex


  • Ana

    My boyfriend would pay you to help me pack this light 🙂 haha

    I guess if I took the time to plan more like you did, I would pack better.
    Toiletries in shoes? Fabulous trick, as you as the toothbrush is taken out of the combo 😉

    Ana x

  • Quinn Halman

    be careful in paris, leandra

  • I’m going to Italy at the end of this month–my first-ever passport-required trip–and I just can’t pack light. I just can’t do it! I’ll be there for 9 days and I just CANNOT make it fit in a carry-on.

    Does anyone else have this problem?! I feel like a failure that I can’t just chicly stuff everything in a tiny bag haha.

    • Don’t feel bad! I am Italian and when I go to visit mom I ALWAYS overpack. Where are you going? Let me know and I’ll suggest restaurants 🙂

    • Charlotte Fassler

      With a 9 day trip i understand packing a bit more!!

      • Leandra’s going for a week, though, right?! And she made it work with four mix-and-match outfits (that are also cool and not just jeans!)! It’s like some kind of magic!

        Since I am not an extensive traveler I’m going to see how annoying the big suitcase is, and if it’s awful I will have to get a carry-on size for Amsterdam (next on the list!).

  • Jaquelyn Swartz

    I wanna come!!

  • Coveting that Bambi skirt, gold boots, Stella McCartney dress, and those perfect Levi’s. Au Revoir Leandra, stay safe!

  • I’m bookmarking this post for future reference!!
    As an out-of-state college student, stuff truly does ruin trips home. I almost tumbled down an escalator with my two checked bags and the maximum number of carry ons allowed. Finally I can have the allure of a light traveler!

  • Leandra, this is genius… toiletries in the boots: nobel peace price (peace because my husband will finally stop complaining about my heavy suitcase!).

    Enjoy Paris

  • I can’t wrap my head around why some people pack so much stuff, and later spend even more time trying to figure out what to wear at the hotel.

  • AlexaJuno

    That suitcase is one of the most satisfying gifs I have ever seen in my life.

    • Yassss I keep watching it over and over haha.

  • LuluM7

    What?! No shoe bags, Leandra?!

  • Liz

    I have obsessive packing disorder – I can’t finished before suitcase is full. With years I have learned to take a small one. Also saves from aliens stealing it as happens with hand-in luggage (honestly, there can’t be any another reason for it happening so often).

  • So you’ve changed my life. You’re a genius.

  • Leftbankgirl

    Always just a carryon for me, then pack a flat tote for the purchases! I agree, pack things in the shoes

  • Mary

    Leandra, where is your luggage in the cover photo from? It has that rare combination of practicality, elegance and gorgeousness!

    • Leandra Medine

      Bric’s! Credited in slideshow captions

  • matilda

    pure awesomeness

  • Those Saint Laurent boots are magical!

  • Glow On

    great post and love the gif! I always overpack…

    New post: The Best Ways To Prevent Bruising From Dermal Fillers and Botox

  • Sarah Moore

    This is something your fellow Americans really need to read. You may still have the best baggage allowance in the world, but Europe is not built for your suitcases (you can’t even buy a large case here!)

  • Marianne Ronsse

    more power to you Leandra!
    I completely agree with you, travelling light feels great.
    It may seem like something difficult to achieve, but once you’ve done it, you feel liberated.

  • Mercedes Rmz

    Brilliant! … No Pj’s?

    • Leandra Medine

      i sleep in the nude

  • leChat

    If packing were an Olympic sport, my Dad wouldve been a gold medalist.

    He’d give this post his stamp of approval for sure !

  • Kelly’s Gross-o

    I wish I could do this, but the fact is that no matter how frequently I shower and reapply deodorant, by the end of the day I always stink. I can’t rewear shirts, which means I have to have an exact day : top ratio…

    On my last trip to Italy I decided to throw caution to the (hope-everybody-stays-up-)wind and bring less, because hey, it was winter, how smelly could I get? Then we decided to make a tagine for our hosts because my bf is Moroccan and isn’t that just so quaint and anyway….all of my clothes stank of onions for the rest of week. So I ended up smelling like BO anyway. Total win.

    • zakariya13

      How are you today, my dear Are you okay

    • Zauberwald

      I was just thinking that there is no way I could ever re-wear a shirt without washing it, because a) BO and b) the crippling fear of awakening the dormant body acne I experienced as a teen! But, this post did inspire me to plan my next packing experience a little better.

  • Olivia McCarthy-Stevens

    Oh jeeeeez, I’m such a (heavy?) packer. It’s because I’m so indecisive, especially over outfits. Going to London for three days in is stressing me out because I wanna take all my best clothes, because what if I most definitely have to change at least 3 times?!

  • Going to Santorini for late honeymoon in June, so you’ve given me way more than i bargained for with this post. How do you say “thankyou” in Greek?

  • Andres Poiche
  • I love this post so much. Practical advice but still fun and with the signature Leandra wimsy.

  • My strategy is usually throw everything in the suitcase, pay extra for my bag at the airport, panic, and then upon arrival conclude I have nothing to wear..


  • Olivia Brandon

    Thank you for the incredible packing advices! I am from these people who can pack the whole house for a moving but cannot pack a simple suitcase for a trip. You helped a lot with these advices!

    Olivia Brandon

  • Alicia

    Very nice read, thanks for sharing! And one more trick from me – when I go on a holiday I usually want to bring at least one hat, so if you’re like me, just put some rolled clothes and put the hat at the bottom of your case. This way it won’t get smashed by the other stuff and you also save space! 🙂 Cheers, my website

  • Stella Marie

    Where did you find these jeans ! they’re gorgeous!

  • Mia

    I love this, “stuff ruins trips” I will have to use this in the future on my unsuspecting friends and family. As someone who has constantly lived out of a suitcase for alot of my childhood and all of my adult life, I cannot stress enough the importance of traveling light. Also no check through luggage is the stuff of dreams when exiting an airport. haha

  • Rosemary

    hi I’m even later to this than I was consistently to high school but I need those gold boots and am distraught that they’re v exp and also sold out, is there a suitable alternative magically floating around out there?