Once upon a time, traveling used to be an occasion to dress up. You can bet your TSA PreCheck that Agatha Christie didn’t have Hercule Poirot in a Champion sweatsuit interrogating murder suspects upon the Orient Express. And real-life people weren’t messing around either. If you’re skeptical, I suggest you google the golden age of air travel—no seatbelts but plenty of colorful hats, flesh-toned stockings, and what I’m guessing were toxic levels of Elnett.
These days, however, with the modern marvels like precision fabric leggings and the distractions of people trying to bring all kinds of crazy stuff onto a plane (anxiety peacock for the win), travel dressing seems to have taken a backseat to comfort.
For me, what to wear when I’m traveling is usually the last thing on my mind. The morning of my departure, I’m normally still trying to shove clothes into a suitcase after only getting four hours of sleep the night before because I was “packing,” aka just staring at a pile of clothes on the floor and stress watching Criminal Minds on Netflix.
So it goes without saying that for people like me, a simple travel outfit is key. I need to think about what I’m wearing as little as possible because if I have too many distractions, I’ll forget to pack both underwear and socks, and lord knows I can only do without one of those.
So throw on and go is the name of the game, and to ensure I end up on the winning side, I like to stick to classic pieces I know complement each other, no matter how they’re worn. Weather permitting, I find a leather jacket, a white tee, jeans, and boots are always great options, give or take a hoodie or scarf, for traveling via plane, train, or automobile.
Thankfully, I was recently gifted my first black leather motorcycle jacket for Christmas (thanks, Mom), and I now have the perfect topper to throw on as I’m flying out the door, invariably late, on my way somewhere. For some reason, this jacket makes me feel very New York and reminds me of that line from season one of Girls: “You’re wearing a black leather moto jacket in New York, so, therefore, you are just naturally interesting.” It goes something like that…
The cropped style and slightly roomy fit of my particular jacket make it an excellent layering option, but on the unseasonably warm winter day of this shoot, as I headed to Grand Central Station, I chose to just throw it on over a simple white T-shirt and hide a hoodie away in my backpack in case the train got super cold, which is pretty much a given.
I’m also never without my Tumi carry-on when I’m headed anywhere for more than one night. I fully expect this suitcase to last forever since my dad still carries one I’m pretty sure he got before I was even born. It’s expandable, so it can hold enough clothes for a week, no problem, and you don’t have to check it, which minimizes the risk of it somehow getting lost in transit. I’ll never understand how that happens. Plus you can monogram it, and all Tumi products have a lifetime warranty.
Over the holiday break last year, I upgraded from a bright blue Herschel backpack to a classic black style just so I could wear all black more often. Necessary? Not exactly. Aesthetically pleasing? You bet. I’m a big fan of Herschel in general because the company’s products are durable and come in a million different colors, so there’s always something to fit your look or mood. This style holds my laptop and all the various books, magazines, chapsticks, headphones, and clothes I shove in it.
My favorite accessories of late are these two really fun pieces in my two go-to colors: navy blue and black. Dr. Martens are seeing a style resurgence at the moment, which I’m not sure I even realized when I stumbled upon this blue velvet pair while window shopping one day. They’re comfortable, on trend, and add just enough interest to an all-black (or mostly black) outfit.
I find shades to be really important when traveling to act as an extra shield to keep people from speaking to me and/or sitting next to me. It works about 30% of the time. These sunglasses are from a New Orleans company I’m newly obsessed with, Krewe, that makes trend-forward but classic styles (and some more out-there ones for when you want to get a little flashy, as we all are wont to do on occasion).
Like Tumi, Krewe offers a lifetime warranty on its products, which this clumsy girl greatly appreciates, and I can’t wait to get more use out of these as the weather warms up and I get to wear them outside and not just as a shield from stranger danger.
As with any form of self-expression, the golden rule is to just do you. But if you’re into these picks, shop similar styles below. Bon voyage, Bitches!
All photos by Steve Jackson.