Ever since I was a kid, traveling has seemed glamorous. No doubt that had to do with a child’s supposition that wherever an adult had to go, that was not around us, had to be very interesting indeed. They would also always carry back some gifts, such as captain’s wing pins, airline-branded playing cards, and the other Jet Age souvenirs from when air travel was exotic. After college, I briefly became a road warrior, one of the low-level drones whose existence dispelled that glamor. Walter Kirn’s/Up in the Air,/a novel about the pointlessness of the loyalty-point existence, came out around the same time.
By that time, the glamor of travel had already become a retro dream, something early issues of wallpaper* magazine built its identity around, self-conscious and thus kitsch. Still, I kept the daydream alive, and the idea of travel informed how I furnished my first apartments (with vintage trunks and other travel items for romance). Since then, the reality of air travel has only gotten more prosaic in its infinitely long lines, invasive searches, racial profiling, and other indignities. Yet, I still travel, and my experiences 20 years ago have taught me how to pack without fantasy. And that is what I wish to share with you.
Your bags: Travel bags should always be rollable and made with telescoping handles. Ideally, if you are traveling by air, you can pack everything in your carry-on, at least for the outbound trip. This is because checked bags force you to wait at the airport for them to come out at the claim. They can also get delayed or lost, forcing you to rely on an airline’s delivery services that can take several days. Lastly, as the snarkily fun/Air Babylon/suggests, checked bags can get pilfered, and since 2001 it’s effectively impossible to lock them. Even locks advertised as TSA-safe can result in your bag arriving half-open and with zippers wrenched-off because the security services don’t care. Since you can’t lock checked bags, anything that has a possibility of being checked should also be anonymous: black nylon with no particular designer marks. Leave the gorgeous Rimowa aluminum on Instagram and the custom-fitted, excruciatingly heavy leather luggage for a car trip. If you have a flashy bag, make sure you can always carry it on and secure it to your other wheeled luggage when you have to race across the airport to make a connection.
Inside those bags, always keep the following ready to go:
Plenty of plastic bags: To store dirty laundry, wet clothes such as swimsuits, leaky bottles of shampoo, or the new bottle of wine that you’re bringing back. You never know when you’ll need them.
Slippers: You’ll laugh at this suggestion until it’s too late and you’re staying somewhere with disgusting floors. From my experience, this eventuality is by no means limited to dodgy budget hotels but can crop up in supposedly leading luxury hotels in Manhattan badly in need of renovation.
Travel tray: To keep hotel keys, sunglasses, change, watch, wallet, and other stuff that’s otherwise easy to leave lying around your room. Available at all price ranges, such trays can be unbuttoned at the corners so you can pack them flat. I love mine.
Plastic utensils: A spare set of plastic knives, forks, and spoons will come in handy when you have to stay somewhere too sketchy for room service. More advanced colleagues travel with nutrition bars.
Clear travel washbag: Regulation sized, of course. In addition to hotel-sized toiletries, you need a compact, concentrated shaving cream. Molton Brown used to make something called Supershave Olibanum that worked very well. Since I can’t find it anymore, I use sample-size tubes of D.R. Harris’ Arlington. I usually keep extra pairs of contact lenses in these and swap them out if my prescription changes.
Travel accessories: A plastic receipts folder, noise-canceling headphones with jack adaptors, plug converters, and spare charging cords. I usually keep extra collar stays in my bag and a cheap pair of ribbon knot cufflinks if I ever mistakenly pack a French-cuff shirt.
Roll, Don’t Fold: Remember to pack clothes by rolling them, not folding them. Doing so saves space in your luggage. Use the small and soft things to fill the gaps in your luggage. You can also use them to pad delicate items or fill the space in your shoes, assuming you bring more than one pair. If you need to wear suits or sport coats at your destination, pack shirts and ties that will go with any business-formal clothes. Roll the ties and keep them in hard-shell items such as shoes so they don’t arrive with creases. To pack a tailored jacket, turn the body inside out, tuck one shoulder into the other, and then roll. You can always hang any wrinkles out when you arrive. Springy tropical wools are naturally wrinkle-resistant since they’re made from high-twist yarns with a natural spring-back quality. If you’re going somewhere colder, travel with a coat that you can take off in the cabin. Also, pack a small collapsible umbrella because it will rain if you don’t.
What to wear when you travel? The days of dressing up to travel are long gone. I can’t say I’m a fan of the other extreme — wearing head-to-toe sweats — because I am a fop. But I’m a fop with perspective, and comfort is essential when traveling. When I have to travel light, I usually wear a pair of my suit trousers. They have side adjusters to loosen them when I try to rest, and their wool generally breathes. I may wear the jacket on the plane as the pockets are useful for travel documents and other essentials. However, instead of a dress shirt, I usually wear a fine-gauge knit, which is more comfortable and softer than a woven button-up. When I travel, I often take only a single pair of shoes, something laceless and made with a rubber sole. Laceless because airports and planes can be filthy, and it saves time having to remove and put them on again at security (which is why I also keep a small shoehorn in my bag). Rubber-soled because you never know if it will rain while you’re traveling. If I have more space or am traveling for pleasure, I’ll often wear lightweight laceless sneakers for the same reasons.
After this, I hope you can stumble comfortably off your red-eye and eventually direct yourself to a shelter where this advice helps you settle, spruce up, and feel you have what you need.