Dressing "en voyage"
The suitcase as wardrobe surrogate
I write to you from my hotel in San Francisco where I am currently procrastinating the re-packing my bags process. I hate packing for a trip, especially now that it’s my job to be perceived wearing (at least) semi-decent fits. It’s one thing to put outfits together at home, with my three unnecessarily well-stocked closets, but it’s a completely different beast when I have to live out of a suitcase. Even when I do bring some exciting pieces - I feel like I just end up wearing the outfit shown below…
I remain baffled by some of my (fancier) peers who live for months in fabulous parts of the world and seem to have different brand-new outfits to wear on every night of their trip. Maybe they’re just better organized than me. Maybe they’re just willing to check 10 bazillion bags. Whatever the case, I don’t travel like that.
And let’s be clear, for the folks I’m talking about, these aren’t your garden variety fit pics. These are pros who are expected to have completely new outfits and styles on deck to keep the likes and views up (and also to appease their sponsors).
For me, the existential agony of packing new and un-tested garments for a trip is simply too great. I only want to wear the stuff that’s tried and true and broken-in. I want to feel like myself and live in the moment, not be futzing with a new shirt or worrying about the lines of a crunchy, unworn trouser while everyone else enjoys a beautiful vista or a delicious meal.
Although it’s entirely human and reasonable (in this internet age) to want to have at least a few looks to send homeward on your glamorous trip, the reality is that travel is not always so glamorous. Travel is too-cold planes and too-hot airports, airbnb mix-ups, long days on foot, and all manner of small inconveniences that won’t make it into your curated Instagram stories. I always feel better having a suitcase of (mostly) practical things I know and love that will console me through any unforeseen hiccups on the road.
Therefore, the packing test - or “what clothes do I have that will get me there and back feeling good” - is actually a really great metric of “how much do I like these clothes.” It’s also a great way to consider a new piece you may want to buy — could I travel with this _____ for a whole week and be happy? And if it passes that test, chances are, it will remain one of those pieces you reach for for (hopefully) years to come.
I understand not all people dress with the same it needs to be practical mindset I have (maybe you’re a steampunk or a furry… (too much “fun” dressing)). And other people are even more militant than I am (dressing like a doomsday prepper… (not enough fun dressing)), but I think this is a pretty good way to look at your clothes.
The pieces that make the grade when you pack will sometimes be deceptively simple, but as Proust says of travel, “…(as the tightening of a string or the more rapid vibration of a nerve produces a different note or color) it gave a sharper tone to what I saw, gave me a part to act in an unknown and infinitely more interesting world…” Being en voyage with your favorite pair of simple work-pants might not be the most original approach (or the most innovative fit) but you’ll already be vibrating on a different frequency, out of your routine and living your life.
For a brief moment, you can feel like the smiling people in a J. Crew catalog. Effortless, living their lives, not even thinking about something so pedestrian as… clothing. When we travel, we become those people we so badly want to dress as - folks who dress up without thinking too much about it. Though my limited selection might lead me to plan a few fits, I inevitably give up on all that in favor of dressing with my gut. There’s nothing wrong with thinking tons about an outfit… I do it all the time, but those brief vacations from our routine and our own closets are something to savor.
After all, choice doesn’t necessarily make our lives any better. Whether it comes to groceries, online dating, or clothing - having a seemingly endless carousel of options doesn’t actually do us much good. Did I buy the right oat milk? Did I make plans with the right match? Did I choose the right pants for a night out?? Our time is limited, but our options are unlimited (at least theoretically).
So basically, if we’re zen enough, we can look at this imposed limitation as a strength. If nothing else it is a reprieve from the clothing FOMO we usually deal with at home.
Stepping out of your hotel in one of your trustiest fits - for me, often a white tee, Ben Davis pants, and a work shirt or chore coat - you can forget about these little inconveniences and focus on being a human being in a new environment. If it’s going to be a long day, I dispense with my beloved leather shoes and just wear the Adidas du jour.
Sidebar: I can’t confirm that it’s my fault that Ben Davis pants are sold out everywhere — I think probably a bunch of people got into them at around the same time, but why can’t they make more?? I heard through a privileged source, that they just have a very old-fashioned approach to production/retail and are not adapting well in a post-covid world. They’ve nixed a bunch of great styles and materials and they can barely keep their stockists supplied. Maybe they should make me creative director and I could get them set straight.
By now you’re probably reading this and either saying, “no, duh,” or “I already dress that way.” In either case, the things we pull from our suitcase can teach us something valuable about all the crap we have in our closets and rarely wear. Don’t forget your statement shirt and your sexy little vintage slacks for those 5 digit-like fit-pics when you travel, but try and reserve more of your energy to finding something sweet and simple so you can just actually live for once.
The pieces…
Shoe
Travel shoes are divided (in my head) into two categories:
Aesthetic: My leather shoes or even cowboy boots that I can put some miles into if I have to, but are not the most convenient. Paraboot Michaels, Blackstock & Weber Loafers, etc.
and the…
All-Day: Usually whatever pair of Adidas Sambas I’ve been into or my Adidas Country. I always prefer good leather shoes and boots over sneakers, but it’s incredibly hard to find that perfect pair that will actually stay comfy all day. When it comes to the all-day sight-seeing marathons, Blundstones work pretty well (as far as leather shoes are concerned and I’m always on the hunt for the perfect 6 inch service boot - maybe from Alden? (I just bought some Paraboot Bergerac boots, so maybe those are the move - I’ll report back.)
Pants
Sue me, but I ain’t wearing shorts in a foreign environment. If I’m at a beach or lazing around a small town in the heat, maybe; but if I’m traversing a whole-ass new city?? I want my legs enclosed and protected. I find a straight leg work pant (especially one you’ve worn in nicely) to be best. Those cotton/poly blends aren’t exactly linen, but once worked in, they drape nicely and they’re pretty much un-rip-able. I go for Ben Davis (as you may know) original fits, but they are so deeply sold out and under-supplied, they can be hard to find. I am very sorry about that, but there are some steals on eBay. Buyer beware, I have worn size 31,32, and 33 that all fit about the same, so check for actual measurements.
Fatigue pants and other military styles are also great, but maybe not appropriate for all settings? Harder to dress up and make you look a bit… overly rustic? Depending on how they are styled.
T-shirt
As much as I love a pleaser and collared shirt combo, this totally affects your outerwear options. Because we’re going for versatility on our trip, I just defer to the classic white t-shirt. As always, I prefer Whitesville tees (I take a size XL, they shrink a full size), but I have a handful of decrepit old Lady White Co. t-shirts that also get some love. Yes, these cost more on the front end, but they last you basically forever — just be careful with spillage - if you’re messy or sweaty, maybe it’s a black or navy tee for you.
Outerwear
A classic moleskin French workwear chore coat is a near-perfect travel companion. The only hard part is finding the right one… this is an in-person cop because they’re all so different and have so many weird quirks depending on the era and overall design. If you want something simpler, the Madewell garment-dyed workshirt is actually pretty fire.
Of course, the other option is a blazer. You know I love a blazer and they are so easy to find vintage. Just look through the racks and find something with reasonably nice fabric and an old-looking label inside. Tweeds are great (if they’re not too itchy) because they have all the pockets of a chore coat but a lot more warmth if you need it.
Safe travels guys. Love you all.
Going to NYC in a week, and then Alaska in 3; couldn’t have come at a better time. You’re a saint, Albert.
Great read! Can't wait for podcast