Dress stylishly and comfortably for holiday air travel

Airport Style

With Thanksgiving this week and the holidays just around the corner, it’s never too early to start planning what to wear if you’ll be traveling to see friends and relatives.

Here are my best tips for dressing stylishly and comfortably for the air/train/car portion of your journey.


I truly believe any travel outfit begins with your shoes.

I learned this the hard way as a rookie image consultant traveling home from my first Association of Image Consultants International conference in Las Vegas. On the final morning of the conference I’d dressed in a stylish outfit with heels and had no plans of donning the sneaker look from the movie “Working Girl” for the flight home a little later.

The heels probably would have been okay if I’d gotten off the airport shuttle at the right stop! I don’t have to go on, do I? Pain and misery ensued!

Ever since, I believe flats are crucial for travel. Of course, if high heels are second nature to you, and you can manage them for miles, you can stop reading (and most likely have already.)

So…flats doesn’t have to mean sneakers (unless they’re fashion sneakers.) It’s simply a matter of finding a comfortable pair of comfortable, stylish flat shoes or boots, preferably slip in vs. laced, that reflect your personal style.

You might have noticed the word “boots” above. Even though boots can be a hassle to take off in the security line, they’re big and bulky, and take up precious room in your luggage, especially if you’re packing carry on only.

All kinds of other shoe and clothing scenarios keep popping in my head as I’m writing, but for today, I’m going to limit my thoughts to casual or business casual travel to and from cold destinations.


While I don’t think it’s necessary to be completely dressed up, there are definite advantages to looking nicer than the average traveler, i.e. upgrades, better service, meeting the man of your dreams in the seat next to you…

Because cabin temperatures are extremely unpredictable, layers are key. Even if you’re wearing jeans, (which I often do) a polished, layered ensemble on your top half will be elegant.

Even when you’re dressed down, there are tons of options options. My favorite outer layer is a cashmere cardigan. Underneath you can choose a knit shell, a pretty blouse, or a stylish t-shirt/knit top. Not a cardigan kind of gal?  Choose a pullover sweater that’s easy to take off. (You still want your layer(s) underneath.) Check out more layering ideas here  if you’re traveling to a warmer destination.

Another way to go is a comfortable jacket. Leather is extremely stylish. Or of course you know I love my black blazer! Your choices are virtually endless, just remember comfy and cozy are your key words.

Wrap up!

A wrap such as a large cashmere scarf,  a blanket scarf, poncho or shawl is absolutely indispensible for plane travel. Any choice as long as it’s big enough can double as a blanket, pillow, etc. Such a wrap is also easy to stash in your tote bag and whip out instantly when the North winds blow on your sight seeing excursions (or if your accommodation’s thermostat is stuck on negative icy degrees!)

On the bottom!

Nice jeans are a natural, but with leggings (read: not yoga) or stretchy knit pants so readily available, there’s truly no reason to have to wear an uncomfortable pant to look stylish while you’re in the air and beyond.

Over it all

Last but not least, I always wear my heaviest coat instead of packing it. If you think you might stow it in the overhead bin, I recommend a dark color.

I would love to hear your favorite airport outfit hacks! Help your stressed travelin’ sisters out by posting your comments below.

Before You Go…

2 comments on “Dress stylishly and comfortably for holiday air travel

  1. Single ladies in particular _ I hope you are reading Dana’s column today! Yes, you might meet the man of your dreams on an airplane. I know someone who did! Layers are definitely my go to for airplanes. You never know if the cabin will be too warm or too cool. Better to be prepared! Thanks Dana!

  2. Yes, I totally agree with Gayla! And even if you’re not looking for the man of your dreams, you really never know who you might meet while traveling. I’ve heard stories of many women coming upon opportunities they wouldn’t have otherwise had by being dressed nicely while traveling.

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