Dockers® Presents the Guy’s Guide: Catch Him if You Can

Editor’s Note: The following series originally published on Dockers.com. Shop the looks now.
Brian Kelly, AKA “The Points Guy”, has always loved to travel. But in 2011 he took that love to the next level by leaving his Wall Street gig and going full steam ahead with his awesome content hub for world travelers and frequent flyer mavens. We took five with Brian to chat about how he works, what he wears, and how to stay comfortable during a long flight.
DOCKERS: You used to work on Wall Street, and now you’re the CEO of your own business. How has what you wear to work changed?
BRIAN KELLY: These days I dress very comfortably: sneakers, khakis, polo shirts, button-down shirts. I used to wear blazers for TV appearances, but I generally like to look casual. I don’t like wearing ties.
Describe your ideal workday look.
Anything comfortable enough for taking a flight. I especially like clothes that breathe well.
What do you love most about the world-traveler lifestyle? And what’s the hardest part/your least-favorite part?
I love how certain destinations can change the way you look at the world and your own life. I love traveling to Africa; it is an incredibly diverse continent, and it’s technically where civilization got started. It’s so amazing, from trekking with gorillas in Rwanda to going on safari in Tanzania, to working with Nobel Prize winner Leymah Gbowee in Ghana to help kids. The hardest part is being away from my beautiful French bulldog, Blue Frenchie Miles. I love coming home from a long time to him tackling me – that love is hard to replicate.
What’s your secret weapon for staying comfortable on long flights?
A lot of airlines will give you pajamas on flights, but the quality varies greatly, so I always bring my own mesh work-out shorts. And wireless headphones keep me comfortable because they can block out crying babies and annoying seatmates. That’s my recommendation: protect your ear waves and create your own environment.