Airport Style
From chic to sh*t and where to fall on the spectrum.
Hi friends,
One of my pet peeves is the way the average person dresses when traveling by air these days. I’m old enough to remember when air travel was an event that required an outfit. My first flight was from New York to Tampa, Florida, where my mother’s brother lived. He was an Episcopalian minister, and his parish was in Tampa. The plan was that the families would spend Christmas together. My mother and her brother were not terribly close; he was seven years older, and this Christmas plan was never repeated, but it sticks in my mind because it marked the first time I travelled by air.
Back in those days, a travel outfit was a travel prerequisite. One did not simply board a plane in anything; a specific, citizen-of-the-world outfit was required. It had to show you were a member of the high-flying jetset, even if you were only a non-passport-holding second grader going to your uncle’s in Tampa. My outfit had the dual importance of being my first travel suit and my first pantsuit. Yes, friends, I’m a child of the sixties, and as such, I was not allowed to wear pants to school until second grade, where we were granted permission to wear a snazzy and intentional pantsuit, which meant a tailored jacket and matching pants.
My travel suit consisted of a navy-and-white fine-striped jacket that buttoned up the center front, then veered off towards my left shoulder, finally ceasing to button at the left shoulder seam. The pants were slim, creased trousers, sans pleats in the matching striped fabric.
Fast forward 50 years, and it’s a free-for-all to get on a plane. I get it, comfort is key, but come on, that doesn’t mean that you have to wear the equivalent of pajamas or your D-list workout wear on the plane. When I flew to Spain last Sunday, I did what I always do: look at the people around me. Chic travellers were few and far between, and flying economy does not give you license to pick old sweatpants from the floor, pair them with an old T-shirt, your b-sneakers, or, god forbid, flip-flops, strap that neck pillow on, and pronounce yourself ready for travel.
Men and women, please believe me when I say, shorts are not OK for a flight, particularly on a transatlantic flight. Cover those legs, show some respect.
So you all see where I’m coming from on this one, I’m a million years old, I remember when people used to dress to fly, it was an event, a happening, and you wanted to look the part. Now, for whatever reason, no one can bear to be the least bit uncomfortable even for a few hours. What looks like the clothing one saves to lounge about the house when one has the flu, and there is no chance of an unexpected visitor, is the common dress code for flying now.
This is what I saw: leggings or bicycle shorts with workout bras and hoodies, and from there it went downhill, plaid pajama bottoms, sweat pants, and T-shirts. I’m not saying you should be dressed to the nines (but what an example you would set), I’m just saying that the entire civility of travel would be raised if people only put a little thought and effort into dressing well for travel. I saw all manner of synthetic fabrics forming indifferent outfits, recalling soviet era gymnasts, breaking the generational divide.
So, in full What Looks Good fashion, let’s take an objective look at dress for flying, where it’s been and where it’s going, and how we can have it all: comfort and style.
The golden years of travel, the 1950s to the 1970s. In 1978, the government deregulated airlines. Competitive pricing and many more routes were added, increasing air travel for the masses.
By the 1990s, the dressing for a flight had become much more casual, with comfortable pants or jeans dominating. Globe-trotting supermodels showed us how it was done with classic wardrobe basics, slim pants, black turtlenecks, white shirts, and above all, comfy, flat shoes. Sneakers and tracksuits were already present, but were considered bad practice.
This is where we are today, even for celebrities. Zendaya, who regularly kills on the red carpet, you’re better than this. Her fit, however, is representative of how the masses are dressing to travel. I object to the overall sloppiness of the look and the slides with socks. This would be a perfect outfit for riding out a hangover at home. Next, we have the very common going to the gym look. A jacket, jewelry, and branded designer merch do not legitimize the look. And at left, what the Bilbo Baggins is Sienna Miller wearing? Biggest bone of contention aside from the fact that the whole look misses and I expect more from her, are the Birkenstocks on the plane. I stand by closed-toe shoes on the plane. I put them in the same category as shorts.
Enough about the negative, let’s explore ways to do it better without sacrificing comfort. It isn’t at all hard. Together, let’s raise the bar for travel dressing.
From the woman who gave you courtroom chic, Gwyneth Paltrow has mastered the art of comfortable, casual, and stylish outfits for air travel. Her choices of cool and casual pants paired with pristine white sneakers, interesting tops, and an important bag show that a good outfit can go the distance with no downside. When I travel, not only does the travel outfit have to count, but the pieces are key to my travel wardrobe and will be worn on repeat. Dress well for the plane and have the pieces with you to be worn throughout.
Why not look like you’re heading to the first-class lounge even if you aren’t? One easy travel formula is to dress monochromatic, as seen above, in all-black travel ensembles. A lightweight cashmere crew neck is a perfect travel buddy that you can utilize when you arrive. A great pair of black pants or trousers in a tropical-weight wool would also come in handy for business travel. Wear flats or sneakers for a perfect and comfortable travel look.
Here are some suggestions for travel-ready clothes that go the distance and may even get you an upgrade; it’s happened to me more than once!
All from Soeur, which is having an excellent sale until Monday, May 25th. The Horatio trousers, striped cotton poplin shirt, crewneck sweater, soft leather flats, and roomy tote.
Or lean into comfort with cashmere sweatpants and a ribbed tee. Pair it with a jacket you’ll wear on the trip, like this bomber, but a blazer would work well also. A soft sneaker and a roomy bag are all you need to waltz right through the chaos of the airport. All are currently included in the Net-A- Porta’s summer sale.
And some more good travel buddies. I love a good travel jacket with plenty of pockets. This jacket is included in the My Theresa Sale, which is well worth checking out for your favorite designer’s pieces, and they have a huge selection of bags on sale. Love the color of this leather tote that gives straw bag vibes and a classy canvas and leather bag. I never get on a plane without a cashmere piece wrapped around my neck. The neutral color of this crewneck gives you plenty of flexibility.
Other Memorial Day Sales of interest are:
The Alex Mill Sale for cotton shirts, great sweaters, and tees.
The J. Crew Sale has everything you need for summer, swimwear in classic styles, and summer linens and cottons, up to 50% off.
If you're a summer espadrilles girl, Soludos is having a MDW sale now with up to 40% off.
That’s what I have for you today. I hope wherever you are, you’re kicking off the summer in style. Happy Memorial Day! Happy Summer! Thanks for reading and supporting What Looks Good. Leave a like and a comment, and please subscribe if you haven’t already!
xxx Jolain















Hi Jolain,
I hope you are enjoying Spain. I just flew home from Europe and could not agree more. We have become a world of traveling slobs. The most ironic observation for me is the absolute overwhelming volume of cheap fast fashion - I was in Madrid - yet most people are dressed horribly. We have access to more clothing than ever before and yet we look worse than ever before. I know I sound like a crabby old lady. Ugh
Thank you for writing this. I find travel so depressing when I see the same dreary “I don’t care” clothes. You can dress respectfully on a tiny budget. There’s no excuse!