Karen Klopp and Hilary Dick article for New York Social Diary, New York Dressing for the winter migration.

The migration of the snowbirds continues as winter chases more and more of us to the sunnier Southern states; taking to the skies to escape to the land where life is lived en plein air and everyone has a sun kissed glow. One sun-seeking friend asked us to simplify dressing on the plane, especially when traveling between extreme temperatures. For this, we reference Packing for Travel, From Jet Set to Trek Set the Definitive Globe Trotting Guide.


What to wear on the plane, packing for travel
Illustrations are by our talented friend, Lara Glaister.

While we may no longer wear “hats, heels and gloves” to fly as ladies have done in the past, there is still a certain satisfaction in boarding with a sense of style and comfort.


What to wear on the plane, packing for travel

The key is layering and de-layering depending on the direction of the flight. Here are our top must-haves for the flight.

What to wear on the plane, packing for travel

Nonstop NYC – PBI


What to wear on the plane, packing for travel
Layer up!

#1.  A great pair of black pants (below left). J. Crew Pixie Pants are a hands-down favorite for fit and flexibility and they don’t wrinkle — even if your flight is overnight!

And our friend Preston Davis of Keep it Chic, loves this Ann Mashburn Flair Ponte Knit Pant (below right).  It comes in a ton of shades and patterns.



What to wear on the plane, packing for travel

#2. Print Top, like this one at Tory Burch. Her silk shirts are just the right note for any occasion to dress up or down. Disembark ready for the office, or lunch with friends.



J. McLaughlin’s Catalina tops are extraordinary for a variety of travel destinations. Very comfy and lots of colors and patterns.


What to wear on the plane, packing for travel
L. to r.: Durham Ruffle Top, $178  Wavesong Tee, $178.

What to wear on the plane, packing for travel

#3. I never travel without a lightweight down vest from Uniqlo. They take up no space, are extremely comfortable, and are an ideal layering piece.



What to wear on the plane, packing for travel

#4. The best cozy item is a cashmere wrap or two to use for style as well as a little warmth when the cabin temperatures drop, even in summer.



Or pop a little tropical color with these Loro Piana Wraps.



What to wear on the plane, packing for travel

#5. The outside layer comes in a few options. Courtney’s Moss’ Glamorpuss is a go-to for both fur and faux.



While perusing Nordstrom, I found these two fabulous Max Mara Capes as investment pieces to add luxury to your travel wardrobe.



#6. Or a reasonably priced Puffer Coat to use as a pillow or a blanket. They are indestructible!



What to wear on the plane, packing for travel

#7. Shoes. As we reported on NYSD last summer on Sneaking up on Summer, sneakers are gaining in popularity for travel and everywhere else in the world. But I prefer a little flat or wedge — without any decorative accents to clear the metal detectors. Note: There was a time when gate attendants had more influence in the cabin and wearing sneakers would prevent you from an upgrade.

Belgian Loafers never go out of style.


Ditto a pair of ballet flats.


My go-to is a pointed low heeled loafer.


And a comfy boot will get you far.


What to wear on the plane, packing for travel

#8. And last but not least, the all-important tote to carry your essentials. Trend Alert:  Oversized totes are all the rage!




What to wear on the plane, packing for travel

What to wear on the plane, packing for travel
Hilary, styling with her cat transporter!

Hilary has learned from the best. “I am used to the days of traveling with my parents, when dad always wore a blazer (still does) and mom always looked chic (still does). I have taken a page out of their book and try to look pulled together but comfortable. I like to wear a jacket with pockets to hold my phone, glasses and lip gloss for easy access. A comfortable shirt or blouse that feels good against the skin and a soft scarf are necessities. I definitely steer away from sneakers; I wear boots or a pump with a heel to elevate my look. Hey, you never know who you will be seated next to!”

Take to the Skies!


As we were finishing up this piece, we noticed one of our insta favorites @blaireadiebee posted her must-have styles for 2023 travel. And as usual, she is right on point.


What to wear on the plane, packing for travel

What to wear on the plane, packing for travel

While researching this article, we discovered The Pan Am Historical Foundation which is a fascinating voyage into aviation history. We thank them for allowing us to use their archival photos. Although times and fashion have evolved (ahem), our excitement for travel has not!

And in the meantime, enjoy a complimentary online copy here.


Packing for Travel, Karen Klopp

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