The Perfect Plane Outfit


After many years of trial and error, I have finally perfected the art of dressing for travel. In naïveté I dressed for foolish reasons: the current weather, the “cute factor”, or the comfort-over-everything style. I loved my hiking boots, so why not wear them on the plane? Or, it’s warm outside, so I should be fine wearing my Chacos, right?

WRONG. And now I’m going to save you the trouble and tell you – this is how you should dress on a plane:


The most important thing to remember about your travel wardrobe is layers. Layers are key to keeping your body at a comfortable temperature.

The best top option is a short-sleeved cotton shirt. I especially love a Target V-neck – they are cheap, comfortable, and a cuter version of a t-shirt.

I occasionally wear dresses when I travel, but not as often as a regular shirt. Dresses are a good pick-me-up if I’m feeling ugly or want to start off my journey looking extra cute. However, always wear leggings with dresses: they will keep you warmer on a cold plane and allow you to move around freely without flaunting those tighty-whities.

Next, you should always wear a sweater over your top. Like I said before, layers are key. The cold air blasts from the nozzles pretty hard, and you don’t want to be stuck shivering the entire flight.

For my outermost layer, I wear a light jacket. You may be tempted to wear a heavy coat in winter, but when you board that plane, the collective body heat of 200 other people on board is going to smoke you right out of it.


Loose-skinny or boot-cut slacks are my preferred pants when traveling. They allow ample room for any movement, including any weird sleeping positions. Infinitely better than jeans in the movement category, and classier than sweatpants, slacks are a perfect middle ground for travel.

Leggings have been a fad for the past few years and are also a good option for travel. If you’re the type that feels comfortable wearing leggings as pants, then I say – go for it! I generally wear leggings only with long shirt-dresses or [actual] dresses.


TOMS (or any other canvas slip-on’s) are my favorite travel shoes. I have traveled in dress shoes, hiking boots, sandals, and tennis shoes, and TOMS are the only shoes that entirely cover my feet without making me sweat. They are also convenient when you are rushing through that long security line – they slip right off!


My leather messenger bag is my go-to carryon for all “normal” travel. It fits my planner, kindle, tablet or laptop, and anything else I should need at a moment’s notice. For budget or adventure travel, when I stay in multiple hostels and carry my possessions everywhere, I take a small 45L backpacking pack. It’s small enough for a carryon, so I don’t have to check it. It also has great back support, and I’m able to easily carry it around wherever I go. When I take my pack, it’s generally the only bag I take, condensing the amount of luggage I have to watch and take care of.

A watch is essential to my travel outfit. Since you can manually change the hands, set it to your destination’s time before you leave. I realize you can also manually do this to a phone, but I like the accessibility of a watch, which is why I prefer it to a phone. Plus, there are so many cute watches out there; why not get yourself a new one?!

I complement my wardrobe with a pair of stud earrings. Stud earrings, though simple, are cute enough to add a bit of sparkle to your look without seeming out of place. Have you ever had a dangly earring get caught on something? If not, then you’re lucky… or lying. Save yourself the risk and wear a pair of stud earrings.


The way I wear my hair is über important to me since I have such wild hair. (Don’t be fooled by my picture – that’s after hours of taming the beast) Ironically, when I travel, I like to wear my hair as natural as I can. I still use products to help control the frizz, but I don’t straighten or curl it. If I wear my hair natural, it lasts much longer and doesn’t become too greasy. This is especially important on long flights, or else you could de-plane looking like you just got out of the shower.

This is my perfect plane outfit – mostly suited for women although the principles still apply to men. Perhaps you have experimented yourself and have some extra tips to add to my wardrobe selections. Leave them in the comments below!

The Wayfaring Woman

You may also like


  1. So I know you say to wear your hair natural, but what do you recommend for the style? Up in a bun or pony tail, or just down? Thanks!

    1. I would wear mine down to start. You can always put it up when you get there, but if I start with it up it tends to get greasier. Also, once I put mine up there’s no going back – it gets a permanent hair-tie kink in it too easily to wear down again.

Leave a Reply

Your email address will not be published. Required fields are marked *