Welcome to The Upgrade, By The Way’s series on travel hacks and hot takes. See how to submit here.
This sounds like an absolute dream, and it is, except for one thing: You have to look amazing every single day. The usual packing pragmatism — layering on the plane, cramming loose cotton separates into compression bags and sticking to a small wardrobe of basics — for the sake of getting it all into a carry-on is basically impossible.
You have not felt the true sting of inadequacy until you are sitting in your second-row seat wearing your little vintage 1980s dress (that felt very Sloane Ranger when you were leaving your hotel!) when a fashion editor walks in wearing something effortlessly awesome.There’s a stylist in an outrageous vinyl dress held together with metal rings, paired with Birkenstock sandals. Or an editor in just the most perfectly crisp black blazer and white trousers with beat-up driving moccasins. Or a writer in a floor-length rainbow striped coat that makes staying warm look like an act of decadence.
It is not the celebrities who make you feel insecure — it’s the other people who are there to work. These are not people sitting in front of hair and makeup chairs, with stylists greasing them into designer duds. They have, to paraphrase the ol’ quote about Beyoncé's productivity, just as many hours in the day as you, and just as many emails to write and deadlines to deliver on.
Besides, refusing to play the game even just a little bit makes you look like a snob. Clothes are supposed to be fun! So a few years ago, I developed a hack for chic: black and navy. It works in a context that demands style because, well, it breaks one of the primary rules of fashion, which is that black and navy are not to be seen together.
But all black was too much for me; color lifts your mood, after all, even if it’s a color (blue) that shares its name with the saddest music genre. And I liked the idea that what felt like ease to me could also read like a daring choice.
Most importantly, it allowed me to boil down my suitcase to a formula, rather than something that felt like the small, terrifying type that appears in the corners of fashion magazine spreads, mostly to inform you that you cannot afford what appears to be a plain white T-shirt. I have a lot of nifty things in my wardrobe, sure, but who wants to cart three suitcases (and hat boxes) around Europe for three weeks just to prove how many Dries Van Noten coats they have? The goal of packing stylishly is to feel like yourself, well-presented.
The first few times I did this, I would pull a navy or black item out of the closet, look at the other items assembled thus far, and ensure that it went with at least three of the other pieces. But I quickly realized that even a slightly quirky pairing looked cool. So I work from a recipe of, roughly:
- Two skirts: something that flows and something that hugs.
- Three jackets: a classic blazer, something weird and an open-front wool jacket (like this by House of Dagmar, which can be belted and layered into myriad shapes, from 1950s couture to German techno DJ).
- One pair of trousers.
- One black dress.
- Three T-shirts (I like Uniqlo’s AIRism shirts, which breathe nicely and have a boxy shape that, again, makes them look and feel like a real “style choice”).
- Black shoes, because shiny black adds texture that helps your rule-breaking combination look very intentional. I bring a low heel, a brogue without a heel and a fancy shoe, because just swapping a casual shoe for a dress shoe changes the direction of your whole thing.
Then you add your small bag of tricks. Scarves of all different colors, tights with polka dot or lace prints, and, the piece de resistance, splashes of red, like crimson cotton dress socks or something with a bit of cashmere. People will notice your cute little red gloves, thus forgetting that you wore that jacket yesterday and that skirt the day before. Because this is true in fashion as much as it is anywhere else: No one is paying as much attention to what you’re wearing as you.
