I'm Always Comfortable Traveling—Here Are the 5 Basics I Do and Don't Wear

The most comfortable basic clothing items for traveling


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I’ve had the privilege of traveling quite frequently over the years for work and pleasure. However, while some people love flying, I’m not one of them. Anxiety city over here. What I do enjoy, however, is crafting the perfect travel look. And I like to think I’ve cracked the code to the ideal airport outfit thanks to my frequent travel schedule.

What it comes down to are ensembles that are comfortable yet fashion-forward. I like to think about it like this: If I wouldn’t wear said outfit straight off the plane to an activity, it isn’t for me. No, this clearly doesn’t mean a full-on going-out ensemble of stiff jeans, a button-down, and boots, but rather a look made up of cozy basics that are still elevated.

While I recently highlighted the carry-on bags I will and won’t use, I thought I’d take this next chunk of time to go over the basics I do and don’t wear to ensure my travel outfits are comfy and cool. So without further ado, keep scrolling to check out my airport style guide—and shop the staples that are ideal for any jet-setter.

Before we jump in, here's a snap of me at the airport in one of my go-to travel looks. (Also note that this is outside of the TWA Hotel at JFK).

Don’t Wear: Fussy Boots
Do Wear: Slip-On Booties

It may seem like a no-brainer, but complicated boots that lace all the way up are a no-go for traveling with ease. I prefer flatter black boots that can be easily slipped on and off. Also note that I tend to opt for boots if I’m heading on a short flight and need a sophisticated yet practical footwear choice for when I step off the plane and head right to an event or meeting.

Don’t Wear: Complicated Lace-Up Sneakers
Do Wear: Slip-Ons

On the flip side, if I am opting for sneakers—a must for longer flights—I always go for slip-on styles. Typically, this means classic Vans because they’re cool (in that retro way) and are also the most comfortable. While I’m not one to typically slip off my shoes on the actual plane, it’s sometimes a must for those extra-long trips.

Don’t Wear: Rigid Denim
Do Wear: Stretchy Skinnies

You’ll never find me in stiff, rigid denim on any flight. Honestly, being that constricted just feels miserable. I tend to stick to my go-to stretchy skinny or straight-leg jeans for comfort purposes. While I’m not usually one to go for leggings or sweats, I have gone that route as well for the super-long-haul flights.

Don’t Wear: Button-Downs
Do Wear: Sweatshirts

I’m quite picky about the tops I’ll wear while traveling. Given that planes are usually quite chilly (but can also randomly get warm), layering is key. For me, that means a soft T-shirt with a cozy crewneck sweatshirt. The vibe is basically like wearing pajamas (but not). You’ll never find me in uncomfortable shirts that are too involved (like fitted button-downs).

Don’t Wear: Heavy Coats
Do Wear: Lightweight and Moto Jackets

Unless I’m traveling somewhere completely frigid, I prefer to avoid super-heavy coats. They get annoying when it comes to storage (especially if there’s not overhead space), and they’re not ideal to wrap yourself in when it gets chilly on the plane. They're bulky, and I often actually get too hot. It’s all about lighter silhouettes like camo jackets or leather styles to compliment an on-trend airport look.

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