Dressing for the Winter Migration

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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.


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.



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

Nonstop NYC – PBI


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.


L. to r: J. Crew Pixie Pant, $98. 30% off with Code RE FRESHAnn Mashburn Faye Flare Pant, $195


#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.


Tory Garden Silk Shirt, $548.

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


L. to r.: Durham Ruffle Top, $178 … Wavesong Tee, $178.


#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.


Uniqlo Light Down Vest, $59.


#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.


L. to r.: Nordstrom Cashmere Wrap, $116 … Nordstrom Tissue Weight Wrap, $99.

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


Loro Piana Wraps, $595.


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


Glamourpuss Tibetan Lamb Soho Coat, $495.

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


L. to r.: Max Mara Alpaca & Wool Cape, $1,985 … Camel Hair & Silk Cape, $1,620.

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


Alala Verbier Coat, $325.


#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.

Belgian Loafers, $575.

Ditto a pair of ballet flats.

Gucci Quilted Ballet Flats, $920.

My go-to is a pointed low heeled loafer.

Patrizia Loafer, $295.

And a comfy boot will get you far.

Aquatalia Low Heeled Boots, $450.


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

Chloe Marcie Suede Tote, $2,190.

Proenza Schouler Tote, $1,090.

Stella McCartney, $1,050.


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!

Tops:  Fawn Puff Sleeve Top, $248  /  Fielding Dickey Coat, $698  / Lancetti Nautical Stripe Sweater, $428   Bottoms: Atala Pant, $498  /  Beverly Skinny Flare Jeans, $228  Accessories:  Tragic Magic Sunglasses, $69   /  Cordel Leather Tote, $770  Shoes: Baxter Bootie, SALE $180 

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.




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.


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