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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