Dressing for the Journey: Travel Outfits That Go the Distance
Weekend Edition #83
Hi!
Between my family’s recent baseball tournament road trips, our Substack NYC boondoggle, and a quick trip to LA earlier this week, I’ve had travel style on my mind.
What to pack, yes, but more specifically, what to wear on the way there.
Because the travel outfit is the compass. It sets the direction for the trip. And ensures that you arrive at your new destination without your style getting lost. (Can’t promise the same for your luggage!)
When you leave home, you still want to feel at home in the world. Your travel outfit needs to show up for you, no matter the conditions. Whether you encounter smooth sailing or turbulence ahead.
Traveling with kids? We need pockets (a lot of them), dark colors (or at least a trusty stain-remover pen), and soft layers to create a safe place to land as we adventure across state lines and atmospheric layers.
Red-eye to Paris, Stockholm, or Shanghai? (A girl can dream.) We want the comfiest clothes imaginable that can still pull double duty when we land and head straight for a chic café because the room isn’t ready yet. (It never is.)
For a work trip we need polished pieces that take us from a 4 a.m. alarms to navigating TSA (and inevitable delays) with colleagues, to nailing the presentation despite being jet-lagged.
Or maybe it’s a getaway with your girlfriends or partner (or the incredibly stylish women I met on Substack who now feel like old friends). This is my favorite kind of travel dressing, the dreamy sort that sets the mood more than the itinerary.
Last week,
left a great comment on this post, and one part stopped me in my tracks. She wrote:“Traveling shows me what works in my wardrobe.”
And then
wrote in her post this weekend about her trip to NYC (where I was thrilled to meet her!):“I am a big believer that one of the quickest shortcuts to understanding your style is to pack a weekend bag. I’ve written about this before but distilling your life into suitcase-sized edit really clarifies what you want to wear like, right now, and what you deem worthy of re-wearing for the immediate 72 hours that follow.”
Both sentiments are so true.
But the flip side is what makes travel style so hard: it also shows you what doesn’t work. What might be missing.
Even when we’re on the go, we still crave feeling sartorially settled. And since I’m sure we all have travel coming up over the next few months, I have some ideas to get us there on time and in style.
Ready for take-off?
LOOK BOOK
When it comes to travel outfits, there’s no one-size-fits-all formula, but there are elements that always work. Dark colors are non-negotiable, and so are layers. Studying and learning from people like
and has changed the equation for me. Where I used to focus on “what matched,” now I embrace layers in black and navy, brown and navy, black, and brown. And I mix in all the metals in my accessories. These shades blend seamlessly without feeling boring. It makes life so much easier (and looks so good, too).
Here’s my travel style roadmap:
1) a dark sweatshirt (easier to wash than a sweater if you’re not sure what facilities await you upon arrival)
2) a soft jacket of some sort, either durable denim with kids or a long soft wool cocoon coat (
just published a whole post about cozy coats this weekend - perfect timing). I also really like how a blazer makes me feel pulled together in chaotic travel situations - very Pan-Am chic.3) a bandana (cotton or silk) or a larger scarf that can double as a blanket
4) cozy socks
The tricky parts are the variables that make up the foundation of the outfit: pants and shoes. For me, the secret is versatility. Wear the pieces that you can repurpose during the trip, no point is wasting valuable suitcase space!
Ok, let’s start with the hardest travel outfits (in my opinion): red-eyes…
PTO: My kind of red-eye
Biz Trip
A work redeye requires a different approach. I used to fly to Amsterdam regularly for work and needed layers that could handle a pre-flight glass of wine with the team, an attempt at sleep, and a professional arrival on the other side of the pond. If you’re my former French boss, you wear your chic Celine high-waisted jeans and change on the plane. If you’re me, you…don’t. I like to leave the house knowing my outfit is ready for departure.
Traveling with your kids
Traveling with your girls
Nothing cooler than denim-on-denim (just look at J.Law!), especially when it’s practical and comfortable to boot.
Back to Work
The goal is to look sophisticated and sleek even at 5 A.M., and even if you spill some Starbucks on yourself (been there).
Wildcard Weekend
There are at least twenty-five years in between two looks, and I can’t get either of them out of my head. I’ve never in my life considered traveling in a skirt, but Cameron and Sienna make it look fantastic, and dare I say easy? Especially with this AYR skirt I found (they seem to have all the best pieces for traveling in style).
IN THE STACKS
- wrote about her experience buying denim at The Consistency Project in this beautiful post about jeans, and so much more.
- is a triple threat: acclaimed novelist, fantastic bookstore owner, and witty substack-er. I loved this behind-the-scenesy post.
Let’s continue dreaming of travel with
’s post all about her favorite spots in London.Sometimes I just like to look at pretty pictures, and
always hits. As does ’s Interior Motives series.8 thing Parisians are wearing this fall? Yes, please! Thank you
!I got to meet
this weekend, and it was the best. She is one of my favorite writers/reporters/marketers, and I love her takes on all topics fashion-and-sports related. We joke about co-writing a Dictionary of Prep (but also, we’re kind of serious if anyone out there wants to chat!!) and her recent post, ‘How to Dress Like You Just Won Head of the Charles,' has many excellent potential entries, like C for Crewneck: so named because rowers were the first to wear the style.I leave you with one of my internet faves,
, who graced us with a post filled with romance novel recommendations (the way to my heart) AND a few of her incredible Halloween-y comics. This one made me legit laugh out loud.
I hope you had a happy Halloween, good luck to all the NYC marathon runners (and spectators), and hello November! Thank you so much for reading, and have a great week!
x Lindsay
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In a nerdy way, I think that airports are the red carpet for us regular folks! 😂 yes — going out to dinner or parties is a great chance to wear cool outfits, but something about an airport— you could be on a flight to Paris with Ina Garten (I was once!) or ordering a drink in the Delta lounge next to Glenn Powell (not me, but I know someone who did). It’s a real opportunity to nail casual style even if the only one who notices is some other mom wearing cool jeans and amazing loafers. Loved this. Xx
Happy Daylight Savings Sunday to all of us with this gem! Love the way a travel outfit is framed as a compass. It’s so true that what we wear en route sets the tone for everything that follows. I'm obsessed w the "Red Eye" (& those cozy COW PRINT SHOES!).
PS - Go The Distance makes me think of the Michael Bolton song from Hercules! A personal fave of mine, lol.