8 Days, 7 Nights, 1 Carry-On Suitcase

  • Here's me and my carry-on, plus a travel outfit utilizing a button-down shirt that would serve as a jacket one night and a bathing suit cover up another day.

    Sonia Rykiel jeans, The Row sandals, Monogram t-shirt, Protagonist button down
  • Outfit A: Granted, you can't see much, and I do wish the first day was photo-documented more scrupulously, but I am wearing an oversized, light blue and white striped shirt that is cinched at the waist with a coin belt I bought in Tulum two years ago. The sunglasses are Gucci, the hair is crazy.
  • As for the night! A very, very easy-to-pack sheer black dress, which you might remember from our thought process of wearing sheer. It folds into the size of a face washing cloth. The make is Dolce & Gabbana and the lace ups are Michael Kors. They're on sale somewhere for like, $80.
  • Another beach lewk: here's a silk twill paisley scarf worn as a sarong plus a light blue velvet bikini by Roxana Salehoun.
  • I wore the bathing suit twice because, why not? This time, with a vest-cape-jacket thing, which was also somewhat velvet and acquired through Ibiza-colored lenses while on vacation. Will I ever wear it again? Who knows.
  • And here's another night outfit -- also an easy pack thanks to the linen pants which fold nicely and, weirdly, look better when creased. The top is basically another form of lingerie and folds into a face cloth a la the sheer dress from slide 3. Notice the travel shoes on my feet.

    Céline outfit, The Row slides
  • No pants, no problem! Here I am in a button down shirt from J. Crew and a Lisa Marie Fernandez bathing suit that comes with...
  • A matching sweater, basically. Two outfits, one pack. How's that for kül?
  • And on !this! night, I practically wore beach wear to da club. Not really, though. The top (Maryam Nassir Zadeh) is poplin, as opposed to neoprene or spandex, and the underwear-and-skirt-in-one (Dolce & Gabbana) is an underwear-and-skirt-in-one. The slides are Peter Pilotto and as you can imagine, pack easily.
  • Arguably the thickest and heaviest garment I traveled with, this linen, off-the-shoulder button-down dress is being worn as a jacket over a triangle bikini (Missoni; obtained for $79 at Intermix just before leaving). Although I have no photographic evidence (damn vacation and its ability to make you believe that you really, truly can unplug!), I did wear it one night buttoned all the way down and off the shoulder, with a pair of stiletto mules and that Tulum belt from day one to boot.
  • For my next trick! There was a striped tank top and orange pants. You can't see my shoes, but they're a low heel stiletto mule -- the same snakeskin ones from this story, as a matter of fact. Easy to pack, easy to unpack. The pants are Rosie Assoulin; I'm pretty sure I saw a light pink pair floating around the Internet on sale.
  • Here's another silk scarf from our pal CJW (remember when she and Harling showed you how to wear them three different ways?), folded in half like a triangle and then worn as a sarong with a striped Lisa Marie Fernandez bathing suit that is so great for tan lines.
  • And for a walk through town? Why, the only other white button-down worth packing (it's linen and Current Elliott) and crochet shorts, of course!
  • Speaking of linen button downs, here's the same one worn over a white full piece from a collab-lab between Pandora Sykes and Hunza G. The sunglasses are Le Specs and the head scarf is just a regular scarf that I manipulated to become a headband. The sandals are K. Jacques!
  • In this outfit, by Rosie Assoulin up top and Natasha Zinko down below, I went to da klub.
  • And on my last day, I put on this Solid & Striped one piece, rewore the vest fringe jacket pillow thing as seen earlier and then ate a cupcake while I watched the sunset steal my vacation.

    The end!
Leandra Medine | August 26, 2016

A story.

There are two kinds of people in the world: those who pack and those who free-ball. That is, those who pack few to none of their belongings before setting sail. The irony of those who free-ball is that in spite of what seems like spontaneity — a sort of  laissez-faire attitude that enables the free-baller to seamlessly transport himself from point A to point B — this traveler is meticulous. Calculated. Planned.

I know this because I have taken to heart advice my dad once gave me — that stuff ruins trips — and turned it into a life goal I consistently try to re-achieve. No matter the destination, the time span for which I will be away and the enumerable and profound Instagram opportunities that might be presented, I take a carry-on. Because here’s the thing: if you master the art of free-balling, you don’t actually have to compromise anything. On the contrary, what you’re left with is a newfangled understanding (or perhaps appreciation) for those who hail from the Camp of Marie Kondo.

My dad was marginally correct when he said that stuff ruins trips, Kondo, however was downright enlightened to declare that one should eliminate any object that does not give them joy from their lives.

What you’ll find above is a slideshow cataloging 15 of the outfits that emerged from the small rolley-bag pictured in slide 1. Granted, I had an advantage (a trip requiring mostly bathing suits, zero pants, and no real need for shoes beyond those of the slipper variety), but this brings up another question that’s really worth asking yourself: do you ever need shoes beyond those of the slipper variety?

While you attempt to answer that, enjoy the slideshow, read the captions, and ask me any questions that might be lingering with regards to the Clown Car Suitcase That Could — it is the penultimate summer Friday after all. Are you headed somewhere?

Photographed by Krista Anna Lewis.