I Travel Over 100 Days a Year—This Is the One Brand I Pack to Look Chic on Every Trip

Wait… how did you pack all of that? That’s the question I get asked the most. Whether I’m at a wedding in Menorca, a work trip in Scottsdale, or a panel in London, someone will inevitably pull me aside and ask, to which I smile and say: I didn’t pack that much—I just packed smart.

I recently returned from an incredibly beautiful wedding held on the Balearic island of Menorca. I stayed at Son Vell, a restored 18th-century estate that’s one of the most stunning properties I’ve had the privilege to experience (think ancient stone walls, lush gardens, slow mornings, and candlelit dinners). And while everything about the trip was romantic and elevated, I was mostly wearing… the same outfit, just styled a hundred different ways.

I travel a lot. Between work, weddings, birthdays, speaking engagements, I’m on the road or in the air about 100 days a year. And yet, I rarely check a bag. Most trips, I show up with just a carry-on and a garment bag. That’s it. So, how do I do it? Ahead, I'm sharing my two hacks for traveling like a pro.

I swear by Pleats Please Issey Miyake for all of my travel outfits. I have the tanks, the trousers, the midi dresses, the long-sleeve tops, the culottes, the sweaters, etc. It’s an endlessly mixable capsule wardrobe that always looks elevated, no matter how exhausted I am. Plus, it all packs flat.

The brilliance of Pleats Please is in the engineering. Each piece is made from a single piece of high-quality polyester, then pressed between two sheets of paper using heat to create its signature permanent pleats. The fabric is featherlight, wrinkle-proof, and shockingly durable. It dries flat overnight in a hotel sink. It never stretches out or loses its shape. It always looks intentional, even if I’m throwing it on between flights or running late to a rehearsal dinner.

Each day while I was in Menorca, I rotated the same three Pleats Please pieces, styled with different earrings, shoes, and layering pieces. One day, it was a sleeveless top tucked into pleated pants with flip-flops. That night, it was the same pants, new shoes, a cardigan draped over the shoulders, and a red lip. It’s the kind of versatility you can only get when you know your wardrobe inside and out and trust the quality.

Secondly, the Away garment bag is my ride-or-die travel bag. It fits up to two suits or three full-length dresses, with built-in compartments for shoes, belts, and accessories. There’s a hook that zips out so I can hang it neatly over a door or in a closet. I slip my laptop and books into the interior pockets, and it slides over the handle of my roller carry-on, like an extension of my luggage. Together, the two pieces give me double the storage without having to check a single bag—a true game-changer.

What I love most about traveling this way is the clarity it brings: Packing light isn’t about sacrifice—it’s about strategy. It means less time deciding, more time enjoying. It’s knowing that your pieces will hold up and, in turn, that you will, too.

I’ve worn Pleats Please on planes, to panels, to dinners, to weddings, to beachside lunches, to late-night grocery runs in foreign cities. It travels better than I do. And when I have my trusted Away garment bag ready to go, the stress of traveling melts away.