For the time being, most business and recreational travel is on hold indefinitely. If you’re still finding yourself thinking and daydreaming about travel though, it’s not a bad time to figure out your travel day outfit for the next time you are able to travel. As an added bonus, in most cases the ideal travel day outfit is also the ideal Zoom meeting outfit. They check all the same boxes: comfort, flexibility, looking put together, and the ability to sneak in a nap without changing clothes.

While I’m not traveling right now (pregnancy + COVID-19 problems in the US), I usually travel pretty often for work, and I have this down to a science.

Air travel, Car travel, ... Zoom meetings...
Air travel, Car travel, … Zoom meetings…

Travel Outfit Philosophy

Yes, I have a philosophy on this. I am not someone that feels comfortable traveling in sweats or pajamas. I like to aim for business casual, but still need to:

  • Be able to sleep comfortably.
  • Fluctuate. Something about being in the air makes tight clothing super painful for me.
  • Not look overly corporate. “Sad business traveler” is a stereotype I like to avoid.

Travel Outfit Components

1. Scarf: Pashmina

A pashmina in a polished and yet forgettable color is one of the most useful travel items. Yes, it’s a scarf. But in a pinch, it also works as a:

  • Travel Blanket
  • Beach Towel
  • Sarong/Skirt
  • Pillow cover (if your hotel pillowcases are a weird fabric)
  • Professional-looking topper over a sleeveless dress or top, when worn as a shawl

As beautiful as the patterned ones can be, the reason I advocate for a solid and boring color is for reuse during a single trip when you might be seeing the same group of people. The one I have is grey, but beige, navy, cream, and black are all good options.

2. Jacket: Cropped open blazer

I generally wear the jacket I’m planning to wear to meetings for my flights. I prefer the “open” style because to me it feels more feminine and goes better with the dresses and skinny pants I like to pack for the rest of the trip (and leggings for travel day). This is another occasion where it is helpful to pick a forgettable color, preferably one that coordinates with the pashmina. While I have a few in black, I generally prefer when the jacket is a different neutral color that goes with black since all my pants are black. I aim to wear it no more than every other day, and generally only need one that I like in my wardrobe at a time.

3. Top: Longer button-down

A longer or tunic-length button down in a soft fabric is helpful for looking polished, staying comfortable, and having the option of removing your jacket if it’s warm. Trust me when I say the people next to you don’t want to touch your bare arms. Calvin Klein always seems to come out with a few good options. I usually look for a black and white print because the colors go with everything else I pack, they’re classic and appropriate for any situation, and the print makes it less obvious if it gets wrinkled during your travels.

4. Bra: Seamless Wirefree

For some reason, when I’m in the air a totally normal bra will suddenly be so obnoxious and uncomfortable that I’m constantly adjusting and squirming around. I can’t be the only person that this happens to. Seamless and wire-free bras in near skintone shades fill this need for me. I say “near skintone” because I absolutely can’t stand beige undergarments. Pinks, purples, maybe some orange or red shades, etc. are close enough for most people that you won’t see it through your top, but also don’t look like medical supplies if a strap peeks out during your in-flight naptime. This is another one that Calvin Klein usually has available.

5. Underwear: Icebreaker Merino

This is probably veering into TMI territory, but this is my favorite travel underwear. As mentioned, all my pants are generally black, but these come in a heather fawn color (a beige I manage to not hate too much) for those who wear other colors.

So here’s what happens when you get on a plane. Youre standing, waiting, carrying things, etc., while boarding the plane. People are lifting items into the overhead compartments, close together, and generally exerting themselves, all while the air conditioning in the plane is off or low. It’s HOT. Then about 25 minutes after takeoff, it gets FREEZING. There is a place that you don’t want sweat hanging around long enough to turn cold on you, and that is where your underwear goes. Merino wool is naturally moisture-wicking, odor resistant, and temperature regulating, which is why you see so many merino “travel clothes.” I don’t like to wear a full outfit of items designed for travel because I think people who do that tend to look like they have never left the house before, but for base layers, these are a good choice.

6. Pants: Black leggings

I’ve written about these leggings before in my post on Zoom meetings. That’s because they are my favorite. I’m sure I will write about them again. I have multiple pairs of these. In addition to appearing (from the lens of a laptop camera to be) respectable pants, they are also the ideal travel pants. With that extended-length button down, they don’t really stand out enough to warrant a second look, and they certainly don’t look like pajama pants. The real beauty to these pants is the wide waistband that doesnt really have any elastic or compression to it. It’s just made of more legging material. These are comfortable enough to sleep in and I can fluctuate (either due to flying or travel diet) without discomfort. Also, this may or may not apply, but they work as maternity leggings as well. That is how soft and stretchy these are.

7. Socks: Dr. Scholl’s Compression Socks

I have terrible circulation. When I fly (between twice a week and twice a month pre-COVID), I turn into an 80-year old. I’m also one of those people that is so naturally sedentary that I can happily get into my seat for the flight, and depending on the duration, not get up again until after we land. Apparently this combination of things, plus flying frequently, puts me at risk for thrombosis and other circulatory issues. Thankfully they now make BLACK compression socks that blend in properly with my leggings and boots.

For the longest time, they only seemed to be available in Suburban Dad White and Medical Equipment Beige. The black ones look like regular socks if you put pants over them.

8. Shoes: Born Boots or Rothys with cushioned insoles

There are two options for in-flight shoes, depending on the weather: Boots made by Born, or Rothys with the regular insert swapped out for a cushioned insole.

Option 1: Born Boots.

This is the option to pick when your destination has cold or rainy weather. Every pair of boots I’ve bought from Born have been comfortable, supportive, warm, and weather resistant. The cost per wear that I get on these is incredible. For travel days, I look for black ankle boots that are either slip-on style or zipper (no laces to deal with at TSA). I don’t like to pack extra shoes, so I make sure that the rest of what I am packing goes with the boots. Generally if I want to look office-appropriate, picking this option means black skinny pants.

Option 2: Rothys with cushioned insoles.

This is the option to pick when your destination has warm or temperate weather. People will hate you if you wear sandals on an airplane, and also your feet will be freezing. Travel days are also not the days to be a hero and wear heels. When I see someone in heels at the airport, I assume it’s their first time flying because airports entail so much walking, and if you’re me, sometimes a decent amount of running. Heels also typically entail going straight to the hotel once you arrive at your destination so you can change into comfortable shoes for walking around. Just skip all that and wear some pointed toe flats. Rothys are machine washable and made from recycled plastic. This particular style tends to work for me with dresses, skirts, or pants, so I can get away with not packing another pair of shoes.

Rothys for travel days

BUT WAIT. THERE’S MORE. Either I am a genius, or I’m just more delicate than the average person, but I like a tiny bit of extra support with these shoes. When I’m traveling for work I usually end up walking 6+ miles a day, and it’s even more than that when I’m traveling for fun. I swap out the inserts these shoes come with for some cushioned insoles which helps a lot. I once took my dog for an (unplanned) 2-mile run in these shoes with the insoles.

Happy travels! Or happy dreaming of travels…

In addition to putting together the perfect travel outfit, with the donwtime of not ACTUALLY traveling it is also a good time to master packing extra light. Figuring out what you need to keep yourself presentable on the road for 3, 5 or 15 days can help you determine what you need the rest of the time as well. As always when getting rid of things, I’m a big proponent of donating them to local organizations instead of throwing them in the trash. It’s better for the environment, the less fortunate (or whoever the organization benefits), and for people who really enjoy thrifting.

donate to a thrift store for your travel castoffs
Think of the thrifters!


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