Philosophical notes on packing - part 2
The reality on the ground
Last week, you got the philosophy treatise, and today, I’m going to get to the packing part. I’ve found it harder to write about!
I don’t actually think of my clothes or shoes as friends or anything other than inanimate objects, but thinking hard about how i do relate to them has helped me make better choices and feel much more like my self when buying and getting dressed. I feel better about moving around the world.
And moving around the wider world is another joy - I work in order to be able to travel. And when I travel for work, it’s almost always enjoyable.
But these things I feel good and secure about, sometimes feel a little rigid, and lacking spontaneity.
Frequently, when I’m preparing to travel, I’m really dialed into relationship with my wardrobe, and I’m thinking about how adaptable it is to a body (mine) away from home, in foreign climates, cultures and dealing with unpredictability. My wardrobe usually feels like a support system, but never more than when it’s shrunk down to a US domestic carry-on sized suitcase + 1 personal item. This is where the combined qualities of utility and emotional support must overlap in 90% of what I pack. Basically every item has to serve me perfectly…. which is a lot to ask. Sometimes I’m well prepared, and as you’ll see, sometimes the best laid plans, well…. we’ll see.
I really really love packing. It takes away any nerves I might have about an upcoming trip, and I start to be and see a version of myself outside of my daily routines.
In a nutshell, my packing strategy for clothing is pretty straightforward, and there’s no complicated algebra about it. Step one is committing to the amount of luggage you can reasonably cart around on your person. If you’re someone who is arriving for a week at the Aman in Venice by water taxi (congrats and), you don’t need a packing strategy from me, because you’ll barely ever touch your own luggage - bring any damned thing you want! Tune in for more shoe news later.
For the rest of you, here’s what I recommend:
Into a suitcase you can manage in & off of trains all by yourself, pack the barest minimum number of tried and true pieces that always always feel great when you wear them in real life, and are functional, comfortable and easy to spot clean. Then add an additional 10-20% more things that feel fun! special! white! less comfortable! and still so reliably the bestest version of you. The “cherry on top” stuff is your calling card - the thing that would make a friend of a friend be able to confirm that it’s you, from across a crowded restaurant.
Though I don’t plan a vacation wardrobe palette, one often emerges as I’m putting it together. In general, the clothes tend to be more neutral toned than in my normal life.
Bring as many small accessories as possible - your tiniest bag that will get you through dinner, to compliment the practical one carry on / day bag. Bring a ton of jewelry options because they are tiny, don’t weigh much, and hopefully feel special. Bring as many scarves as humanly possible. Go wild with color/print/pattern here (especially with belts)!
For me, keeping this edit tight is all quite doable… until we get to footwear. Sadly, my life’s work takes up way too much suit case real estate.
When I’m traveling for work, this is easier. For most trips, three pairs of shoes is the correct number. Each pair must be able to be worn in a number of settings. The categories are:
Ultra comfy for day (sneakers, ballet flats, espadrilles, easy sandals, etc)
Comfy but good looking for day OR for low key evening plans (loafers, strappy sandals, mules that stay on, low block heels, etc. Nothing athletic or adjacent)
Less practical, more dressy but still walkable shoes for dinners out / parties / events (Sky’s the limit, here, if you know yourself well. Mad props to anyone who ever packs boots higher than the ankle)
When I travel professionally, I’m usually on my own, and any group I join is generally well dressed, so I just need to keep up appearances, and I never worry about being the best dressed. I work in fashion, it’s impossible.
But warm weather vacation packing is where I lose my discipline with footwear entirely… I want indulgence! I want extra fun! I want to look good in the photos! And frequently I feel the urge to use this as an excuse to buy new stuff, just for the hell of it. The weeks leading up to my trips are the hardest to keep my cool, and not over-buy without intention.
So, I’m leaving for a vacation in Sicily in a week. Most of it is a road trip - staying in multiple locations, packing & unpacking every few days. I’ve committed to bringing as little as possible. I’ve bought a few new things for the season (slightly earlier than I might have in order to pack them) - a silk camisole and a slinky black high necked tank. And one thing that I’d probably never buy otherwise - a really functional pair of water sandals, as you know.
And now, the rest of shoes are starting to stress me out.
I’m definitely surpassing the three pair limit. How do you go to an island (two, actually) with fewer than 2 daytime sandals? The Xero sandals we examined in the last post are basically the size of socks, so they don’t count… or do they? Will I wear them walking around towns during the day? These are never going to be a real part of my wardrobe, so they’re kind of a wildcard, and are throwing off my game.
In addition to a pair of leather Keds-like sneakers, here’s what’s definitely coming with:
All super comfy (now that the K Jacques are broken in), and at least 2 of the 3 are appropriately for day walking. The red sandals work for a more “grown up” dinner / theatre / evening activity. If there were no such thing as weather, I’d be set - my three pair normal limit, plus the water sandals. Reasonable.
But sneakers will not go out to dinner in Europe, ever. And sandals will be ruined if there’s an evening downpour. Adding a 5th (ugh!) pair is only allowed if they serve a dual purpose.
So, naturally I’m dreaming of new acquisitions that are both daytime-walkable and elegant enough for rooftop drinks & dinner - these or these or these. All great, but I DO NOT NEED ANY NEW SHOES.
I AM NOT BUYING ANYTHING NEW, SIMPLY BECAUSE I DO NOT KNOW IF IT MIGHT RAIN IN SICILY. This goes so fully outside of my philosophy, that it would break the spell of vacation indulgence.
If my closet is full of shoes that make me feel good, surely there is something I can work with. Here are pairs I’ve be auditioning for the last week or so:
They all will work FINE, and I’m not terribly inspired by any. The Hermes ballets feel too tailored, the metallic ones feel too covered up. And the Greek fishermen are really so worn, they’re not restaurant-dinner ready. The amazing Jil Sanders feel a little tooooo fashion, but are the likely culprit.
Or, should I just throw caution to the wind, and ignore the possibility that I’ll need to manage to look presentable while dodging puddles?
I’m not good at math, and this suddenly feels like an equation that I can’t balance. Sometimes our tried and true philosophies and travel habits don’t serve… Am I reevaluating my relationship with my entire wardrobe? My 3-pair limit?
Or do I just need to throw a few things in a bag, and escape overthinking the whole thing? Perhaps, like this two part series, in which I try to mesh two ideas about my wardrobe - the idealism vs the schizophrenic fashion person, I’m just over thinking the whole thing, and missing my chance to narrow my goals for more success.
We shall see!
My next installment here will be more inside-baseball - how the shoes get made, who is involved, and a slightly dishy glimpse behind the curtain….
Stay tuned. (And tune into Insta for the final shoe tally - this series is already too long!)