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Planes, Trains & Khakis with Scott Keyes

Scott Keyes is a traveler. His wanderlust runs so deep that he decided to turn travel into a full-time job. And for a man whose office is literally anywhere that has wi-fi, there’s no time for clothing that doesn’t provide the flexibility his lifestyle needs. We sat down with Scott, founder of Scott’s Cheap Flights, in a rare idle moment and asked him a few questions about how he manages to stay Always On.


"Traveling means pushing ones boundaries, exploring unknown parts of this world and learning that despite all the wonderful cultural nuances, we’re not so different after all. It’s the best way to learn not just about other parts of this Earth, but also learn more about who you are and where you come from. Until you step foot outside your home, you miss so much of what makes it, and you, unique."

D: How do khakis fit into your lifestyle?

SK: They fit my lifestyle perfectly. They are versatile. I don’t have the time to focus so much on what I wear, so I need clothes that are versatile, modern and make me look presentable.

D: What difference does Scott's Cheap Flights make in the way people travel?

SK: We help make international travel possible for people who thought it was unaffordable. Tens of thousands of people have told us about honeymoons, vacations, or visits to old relatives that they didn’t think they’d ever be able to take until we emailed them about a 250€ return flight between Europe and the United States or a 300€ return flight to Asia.


"At the risk of sounding cliché, the world is my office. Some days it’s a coffee shop, some days it’s a brewery, some days it’s halfway around the world. I’ve sent out deals in a rural Borneo hotel, while touring through the British Museum, even while on an airplane. Anywhere there’s an internet connection, that’s my office."

D: You have a 10-hour flight ahead of you. What features are you looking for in your pants?

SK: First and foremost, comfort. You’re only as comfortable as your pants, after all. Second, pants that stay cool and dry, despite being in a hot stuffy plane. Finally, the fact that as soon as I leave the airplane I can go directly to work, a business meeting, or a restaurant and not need to change pants.

D: After wearing the Dockers® Smart 360 Flex Jogger around the world, what is your favorite feature?

SK: The 4-way stretch fabric, definitely. The fabric is soft and versatile, so it’s perfect for my lifestyle, since I’m always on the go, working and/or travelling around the world. I could wander around the streets of Delhi, then play cricket with some friends or end up having dinner in a fancy restaurant, all without having to change.