All My Travel Outfits Follow These 5 Rules (2024)

One perk of my job is that I travel a lot. This means I've had a lot of time to master the art of packing a carry-on, figure out the fastest way to get to the airport (which actually isn't all that fast in New York), and most importantly learned exactly what—and what not—to wear. All it takes is one red-eye pretzeled in an exit-aisle seat to know your outfit choice can make a pretty big difference.

My first key bit of advice: slip-on sneakers. This TSA-approved footwear choice not only makes navigating security a breeze, but it's also ideal for subtly sliding under your seat without the fear of having to fumble with shoelaces or fitting swollen post-flight feet into anything remotely high-top. Second, the clothes I choose my outfit using the stretch test. Doing a few quick lunges and an arm reach, I always calibrate: Does my bra ride up? Do my pants squeeze? Does my jacket constrict? If the answer to any of the above is a yes, I immediately abandon my choices for something comfier.

If I can get away with it, the stretch test means that the majority of my travel outfits are basically a lesson in head-to-toe athleisure. Sweats, a sports bra, and a cozy sweatshirt are all designed with comfort in mind, which can make a world of difference seven hours into a transatlantic flight. If I need to look a little more polished post-flight, I'll make sure to have a cool jacket handy and to wear jeans that I know are stretch enough to keep me happy. Below, I've highlightedthe five key rules I always follow when flying along with some shopping (and outfit ideas) for your next trip.

The Stretch Rule

Before you leave the house and head for the airport, take a minute to do a few lunges, arm swings, and other stretches to ensure your travel ensemble won't cause any problems.

The Carry-On Rule

I try to always carry-on my luggage when I travel, and besides my suitcase I make sure to have a bag that can hold whatever I might need in flight. A sizeable tote or backpack is always key.

The 2-Second Shoe Rule

Navigating TSA is tricky, but I always make sure to have easy to remove shoes just in case. A slip-on sneaker or comfy pair of flats are great choices.

The 20-Degree Rule

Temperatures tend to fluctuate in flight and while it might be toasty when taking off, it's freezing halfway through the flight. I always make sure to dress in layers, and be ready for the temperature to rise or fall as much as 20 degrees.

The Smart Accessories Rule

There aren't many times I condone wearing sunglasses indoors, but when flying I try to pack accessories that can help make the experience easier. Sunglasses or a hat can help with napping. A scarf or jacket can act as a pillow. It's all about making things multi-purpose.