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How to Travel During the Holidays Without Looking Like You're Miserable

Even though you are.

In our latest column, "Ask a Fashionista," you can solicit our strongly held opinions on everything from how to wear a midi skirt without looking like a tree stump to whether a certain retail CEO should go ahead and resign already. Have a question? Email us at

Q: I always end up looking like a slob when I fly home for the holidays. What can I wear that both looks good and is comfortable for long, annoying flights? — Christy, near Pittsburg, PA

I don't have to remind you that airplane travel used to be occasion to dress to the nines. We've all seen "Catch Me If You Can" and ABC's "Pan Am" (actually I was probably the only person who saw that, being as it only lasted one season, but it was good y'all). Airplanes were like luxury hotels in the sky. Flash forward to present day where flying is, at best, a physically and emotionally draining way to sit uncomfortably for several hours and, at worst, a mind-numbing series of never-ending lines and fees and delays. 

But style doesn't have to negate comfort, which is the key element of any travel outfit. Whether you are going straight to a family reunion or need to catch as much sleep as possible on a red eye, it's time to step up your look no matter what the holiday travel season throws your way. 


The sportswear trend that is everywhere right now is actually perfect for traveling. Silk trousers with some stretch are easy to sit in for hours and sleek sneakers are perfect for dragging around luggage. Metallic details, like the gold panel on this sweatshirt, upgrade the look without sacrificing softness. Top it off with a ultra-modern watch and a versatile tote and you are ready for clear skies.

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1. Gold foil sweatshirt, $78, available at J.Crew; 2. Rio Runner sneaker, $295, available at Loeffler Randall; 3. DKNY striped silk-stretch pants, $235, available at Net-a-Porter; 4. Kenzo 3-Point watch, $705, available at Opening Ceremony; 5. Berliner oversized satchel, $234.50 (from $268), available at Madewell.


This is the trickiest scenario. The easiest way to wear something your grandmother would approve of without feeling constricted is to find a loose-fitting jersey dress that makes a statement all on its own. Pair it with sensible loafers and a long soft coat you can use as a blanket in-flight or easily stow in the overhead compartment. For finishing touches, add a touch of pearls (classy but easy to remove during security) and a structured bag that is as roomy as it is elegant.

1. Cleo suede loafers, $150, available at J.Crew; 2. Gold Philosophy open bar ring, $148, available at Shopbop; 3. The colorblock large A satchel, $375, available at Kate Spade Saturday; 4. Raw edge printed dress, $115, available at Cos; 5. Julia textured long coat, $575, available at Whistles.


Never underestimate the power of layers. Especially when you anticipate cancellations, long waits on the runway and a general desire to sleep no matter who is crawling over your aisle seat to get to the bathroom. This is the perfect situation for  knit pants, basically a fitted blanket for your legs, and a poncho-style cardigan with a hood for protecting you from the dirty shoulder rest. Choose layers in tones of the same color and the result is something like travel camouflage. Then all you need is a bright beanie to keep your spirits high and noggin warm. 

1. Stella McCartney Curtis oversized two-tone wool-blend felt coat, $1006.50, available at the Outnet; 2. Knit flared trousers, $99.90, available at Zara; 3. Hooded two-tone poncho with piping, $99.90, available at Zara; 4. King felt slip on sneaker, $120, available at Kenneth Cole; 5. Heattech turtleneck T long sleeve, $14.90, available at Uniqlo; 6. Acrylic watch hat, $20, available at Carhartt.