Traveling Chic
How to look good for the long haul.
My favorite Italian ponte pants that I turned all my followers onto for long haul travel have unfortunately been discontinued by the powers that be at J.Crew. Due to this development, some readers requested that I come up with alternatives for the upcoming fall and winter travel season.
You can’t go to any website or Substack without seeing an ode to 90s travel style. Supermodels and celebrities always looked put together and probably stayed in shape by carrying their heavy bags before the advent of wheeled luggage.
Cindy Crawford always looked presentable at the airport but not many people are wearing jeans for overnight flight these days.
For this post, I was inspired by a few of Cindy’s airport looks and her daughter Kaia Gerber, who reflects how most people dress to travel today.
Technically, I think Kaia just wore this outfit in NYC but it definitely looks like something she’d also wear on a flight.
I’m sure Kaia is wearing an expensive designer trench but this double-breasted cotton trench coat is very reasonably priced.
I personally like wearing either a matching set or at least a top and bottom in the same color. One caveat some people had was that whatever I found for travel be machine washable. This merino wool hoodie and matching merino wool pants can be washed in cold water and hung to dry. Just don’t put them in the dryer unless you want them to become child sized.
I almost always wear sneakers for long haul travel since there is always so much walking between security, passport control, and the gate. These suede-trimmed leather sneakers would also look very chic with long wool trousers during your trip.
For Air France flights to Paris, I always get away with a crossbody bag, tote bag, and a carry-on suitcase but Delta is cracking down on the third item so be careful with them.
Hopefully, the gold passport cover is bright enough so you don’t lose it anywhere.
I was inspired by Yasmin’s hats on Industry so I included one for every outfit. Hers were custom made for the show the wardrobe department but I wish they would sell them to fans of the show. The grey brushed merino wool baseball cap is perfect for hiding bed head after an overnight flight.
Hide your tired eyes while still being able to see with the chic gold aviator sunglasses.
“Travel and change of place impart new vigor to the mind.” - Seneca
I don’t think many women are wearing a suit on a flight like Cindy unless they have a meeting directly upon landing. I did manage to find one that would be very comfortable if you did need to travel to a meeting with colleagues.
The everywhere ponte blazer and matching cropped flare ponte pants have stretch for ease and also come in black.
Add a matching navy cashmere sweater or mix it up with one of the other 17 colors.
I bought these suede-trimmed sneakers and they are the most comfortable sneakers I’ve ever worn. If they weren’t so expensive, I’d buy a back up pair.
I love using the Attersee Jacquard Brea bag as a pouch in my tote bag during travel but when you snap the sides, it becomes an evening bag. You can match your outfit with the navy matte carry-on or pick a contrasting color.
Choose a bright green passport cover that won’t get lost in your bag.
If you’re headed to NYC, hide your messy hair with the green Central Park hat.
Maybe they are too matchy-matchy with the green but I love the light green sunglasses.
“Wherever you go, go with all your heart.” - Confucius
Kaia was wearing this look at the Nice airport after leaving the Cannes Film Festival last year.
This twill trench coat is a great budget friendly option.
Two years ago, all my followers and I bought the Gap CashSoft sets for long haul travel for fall and winter. It might be time to revisit them. This grey shaker-stitch crewneck sweater and matching shaker-stitch pants also come in five other colors.
If you’re headed somewhere cold, you’ll love these shearling lined suede sneakers.
Add a little pattern with the mini Gucci mini crossbody bag that pairs well with the brown suede tote and the Hartmann Tweed carry-on bag that’s similar to the old one I own.
Finish things off with a chic nude croc-embossed passport cover, brown suede baseball hat, and tortoise shell sunglasses.
If you want the exact details on her outfit, you can find it on my LTK page.
“There are no foreign lands. It is the traveler only who is foreign.” - Robert Louis Stevenson
Every outfit is a choose your own adventure roadmap. I included a camel double-breasted wool and cashmere-blend felt trench coat since that’s what Kaia and Cindy are wearing but you could swap out any of the other coats in this post. I’d personally wear my checked wool Max Mara coat with this outfit.
I love the color of this vintage soft raglan sweatshirt and matching wide leg sweatpants but they also come in 13 other colors. The pants also come in a high-rise boyfriend jogger style.
Add a little color to your neutral outfit with these suede-trimmed sneakers.
If you’re worried about getting in trouble for a third item, you can hide your crossbody bag under your coat while you walk onto the flight with your tote and carry-on bag.
The blue passport cover is another one that won’t get lost in your bag.
The baseball hat trim picks up the color of the bags and the sunglasses would go with any color.
“Travel makes one modest. You see what a tiny place you occupy in the world.”
- Gustave Flaubert
You can use the removable scarf on this chic brown oversized double-faced wool coat as a blanket on the plane. It also comes in three other colors.
The CashSoft crewneck sweater and matching sweater pants come in many different colors if brown is not for you.
Kaia was seen in NYC in black Nike Cortez Sneakers and Jeremy Allen White is a big fan of them too so you’ll be in good company if you wear these Nike Cortez sneakers.
You can go wrong with a neutral crossbody bag and a Rue de Verneuil tote for travel. Floyd is a new-to-me luggage brand but I love this bronze carry-on suitcase.
If you want a jump on your holiday shopping, you can gift monogramed passport covers to everyone on your list.
Let everyone know you’re a New Yorker with the NYC hat. Don’t forget your glasses so you can make sure you can read on your trip. I actually pack two pair of glasses for long trips in case I lose one pair.
“The real voyage of discovery consists not in seeking new landscapes, but in having new eyes.”
- Marcel Proust
If black is more your speed, start with the black oversized wool-cashmere wrap coat. Cindy and Kaia both wore black when they were in Paris for the Olympics.
The black fancy cashmere crewneck sweater is what I wear on overnight flights since it’s lighter and doesn’t make me overheated.
The black wide-leg double-knit jersey pants could be a good replacement for the discontinued Italian ponte pants but I have to warn you that they are dryclean only. There is also black double knit track pants that would work for travel too.
I own the Owen sneakers from The Row in taupe and ivory and can attest that they are insanely comfortable.
Make sure you don’t snooze on Celine Homme because they have some great pieces like this Celine Triomphe leather trimmed logo print crossbody bag. A similar tote to the one Kaia has been seen carrying on many trips is the Celine Triomphe logo print tote.
Kaia’s carry-on is the Away Bigger Carry-On.
Don’t forget your passport, fun hat, and sunglasses for your next trip.
“Travel isn’t always pretty. It isn’t always comfortable. Sometimes it hurts, it even breaks your heart. But that’s okay. The journey changes you; it should change you. It leaves marks on your memory, on your consciousness, on your heart, and on your body. You take something with you. Hopefully, you leave something good behind.” - Anthony Bourdain
In summer 2023, I wrote a big travel post, My Favorite Travel Tips, Tricks, Advice, Products, and More, that I updated and reposted in March 2024. It’s filled with everything you need to make travel by planes, trains, automobiles, and Jitneys, easier.
Hopefully, you are now covered for anything travel related but if not, feel free to ask questions in the comments.
XOXO,
HC
“The world is a book, and those who do not travel read only a page.”
"For Air France flights to Paris, I always get away with a crossbody bag, tote bag, and a carry-on suitcase but Delta is cracking down on the third item so be careful with them." I've always tried to make sure that *if necessary* I can "stuff" my crossbody bag inside my tote, or my tote inside my carry-on.
Fabulous post Heather 🥰 so many chic looks. I love what Banana Republic is doing this year BTW. Also I do hope you are feeling better. It can take a good 6-8 weeks to really feel like your self again after surgery. Rest and restore 🥰