Here's How I Stay Stylish When I (Literally) Travel All the Time

I don't get off of six-hour cross-country flights looking awesome — who does? — but I can passably walk into a business meeting without my stomach being covered in red lines from uncomfortable, crushing waistbands.
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Kathleen Braine
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I don't get off of six-hour cross-country flights looking awesome — who does? — but I can passably walk into a business meeting without my stomach being covered in red lines from uncomfortable, crushing waistbands.

In the past couple of years, I officially became someone who "travels all the time for work." At first it was almost thrilling — I furiously researched a new carry-on, I signed up to airline loyalty programs, I began to collect frequent flier miles, I was embarrassingly excited to apply for TSA Precheck (I got it, yay!), and despite the fact that I was often harried and stressed out running through airports, I relished the fact that somehow, my constant movement made me feel more like a "real" adult (however ridiculous that may sound). Yet, despite my initial excitement, it didn't take long for me to become the jaded business flyer of Hollywood movies and LAX airline lounges. I was suddenly that person who hops on a flight and then immediately gets off the plane to Uber directly to another meeting. Even more unexpectedly, the young girl who used to cry with anxiety when she got to the airport even remotely after the designated two hours pre-flight boarding time suddenly became a woman who gets to the airport a casual 30 minutes before her flight is set to board and still stops for a Bloody Mary before reaching her departure gate.

Notably, one of the bigger changes that developed when I began to spend more time on planes, trains, and airport shuttles was how I approached dressing for a flight. When I was younger, my biggest priority when I flew was always predominantly my own personal comfort. I would wear sweatpants, sweatshirts, tights, flip-flops, or terry cloth shorts (...it was 2003), and I would carry my panda Pillow Pet along with me — up until I was 20 years old. (In my defense, they are a remarkably functional and multipurpose stuffed animal, and I was moderately afraid of flying up until my early 20s.)

Kathleen Braine Visa photo

My passport photo.

This "comfortable" attitude toward flying, though it was pretty common amongst my friends at that age (and honestly, quite a lot of my peers now), is something that is relatively new in the history of commercial air travel. In the '50s and '60s, passengers were expected to dress up as if going to a cocktail party to fly, and the flights were described as glamorous and luxurious. Definitely not the words you think of when you envision the bleary-eyed and crowded 7 a.m. line for coffee at Newark airport. Despite many a nostalgic think piece harkening back to those "glory days" of air travel and the fashionably dressed passenger, I still think we are ultimately better off today. After all, up until the early '90s you could smoke on airplanes (which by most accounts, was horrible for everyone involved). That does not sound "romantic" or "glamorous" to me.

That being said, as I became a more "seasoned" business traveler, I realized there were ways to look sleek and fashionable while traveling and still manage to dress comfortably. I don't get off of six hour cross-country flights looking awesome (who does?) — but I can passably walk into a business meeting without my stomach being covered in red lines from uncomfortable crushing waistbands. I'm pretty sure that's a win-win. Here are my travel staples for looking good but also staying comfortable. Tell me, what do you guys wear while you travel?

Leggings

I will say this until the day I die: Leggings do not have to look sloppy. They can be just as stylish and sleek as pants, and they also allow for ease of movement and comfort during multiple hours spent crammed in an airplane seat. The key is to find leggings that are just as thick as pants and that can also apply minor compression without strangling your waist. My longtime favorites (I've accumulated seven pairs since 2007) are Zella Live-In Leggings, but there are many other brands that accomplish the same thing.

Here are some other favorites to check out:

Oversized Sweaters

Planes are notoriously very, very cold. Instead of forgetting about this until the last minute and buying emergency plane sweatshirts on my layovers (what's up, Colorado sweatshirt!) — I've finally adapted to the cold by wearing stylish and, most importantly, warm oversized sweaters during my longer plane flights. Here are some of my recent favorites:

Chelsea Boots

Even though I no longer have to take off my shoes when I go through airport security (once again, thank god for TSA Precheck), I still throw down for the perfect airport shoes: Chelsea boots. They are sturdy enough for walking around an airport, they slip on and off easily, and they allow you to also wear socks to keep your feet warm on the aformentioned super cold plane. My Cole Haan Newburg boots have been my favorite shoes for more than five years, but there are many other amazing Chelsea boots in the world for your travel needs.

Long and Soft Dresses

I never used to imagine that there would be a world in which I would willingly wear a dress on a plane. However, there is something so perfect and cozy about spending a long plane flight in a long, relatively loose-fitting dress. The best part? With the right dress, you can literally walk straight from the plane into a business meeting and THEN turn right around and head to happy hour. For this hat trick, I recommend going with a black or navy dress. Here are some of my recent coveted dresses:

Soft T-Shirts

If you're wearing the aforementioned leggings and sweater, the best choice of clothing to wear underneath everything is a super-soft T-shirt. These brands offer shirts that are devastatingly soft but still chic, which is pretty much all you can ask for on a cross-country flight. Once again, I recommend going for a darker color:

Jumpsuits

Last but not least, as I've mentioned many times, I'm a huge fan of a good jumpsuit or romper. For traveling, comfortable and flowy rompers are the perfect choice, as they can make you feel like you're wearing pajamas when you don't look like it (mostly). I have recently been very taken with oversized rompers, and although these may seem a little baggy for office wear, once you step off the plane you can always tailor them with a nice belt:

Bonus notes: When you're on a plane and trying to still look your best, it's important to also take care of your skin and hair. As I've mentioned before, I'm a big proponent of putting my clean, damp hair in French braids before any flight and letting it air-dry on the plane so that it is wavy and frizz-free when I land. I've also gotten super into bringing my Glov makeup remover with me when I travel so I'm never stuck with mascara smudges or caked foundation after a crazy-long flight.