On the Road with Yale Breslin

Whether it’s chasing a story, shooting a movie, or pitching an innovative new technology platform, our favorite cultural innovators are always on the move — and showing off their style while they do it. On the Road follows the most stylish and interesting culture-makers and takes a look at how they travel. 

Toronto native Yale Breslin has been immersed in fashion for years as a style journalist for outlets like GQ, Esquire, Elle, and the New York Times Magazine. Most recently, he was tapped by Hova himself to launch the style section of his site, Life+Times. Not too shabby, Mr. Breslin. We chatted to nail down this fashionable traveler’s must-haves. (All photos are by Mike Bogart.) Read on to find out how you can win the UGG for Men Huntley kicks Breslin is sporting here.

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What are your top 3 must-pack items when you’re traveling for business? What about when you’re traveling for pleasure?

Business: One white dress shirt, a pair of brogues, and a pair of pants (not jeans) that can transition from day to night. Plus, I always bring workout clothes with me (you never know when you’re going to get your sweat on). Pleasure: Sweat pants, my oldest and most comfortable tee-shirts, and a baseball cap. Told you, comfort is key.

Any frequent-flier tips to stay sane at the airport or on long flights?

Always check your flight is on time before you head to the airport. I’ve learned the hard way. Also, if you’re VERY nice to the ladies and gentlemen working behind the counter, more often than not they can get you on an earlier flight… and if you smile a lot and compliment their hair, usually they won’t charge you the “change fee.”

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What’s your travel footwear must-have?

Whenever I’m traveling, along with my favorite pair of UGGs (especially for Canadian winters — I swear by their boots), but a classic and comfortable running shoe is never a bad idea. Working out is part of my travel plans; I have to come equipped.

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Give us some recent in-flight reading or music you’ve enjoyed.

I’ve been listening to a lot of Lorde — the 16 year old from New Zealand. Her recent single “Royals” has been on repeat nonstop. I don’t love flying, but something about this song calms me down. While I don’t have the patience to get into a good book on the airplane, I always divert back to Vanity Fair. Their articles are lengthy and always capture my attention… for long enough before I’m onto the next article (without getting bored). Plus, sleep! Lots of it.

What do you do to keep your feet comfortable during your travels?

Cashmere socks on a plane are a lifesaver. It may sound pretentious — but if you’re on a long flight and want to take off your shoes, your saving grace lies in cashmere socks. Bare feet on airplanes should be illegal along with drugs and guns.

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What’s the coolest place you’ve been?

I went to Cannes for the first time this year and that was quite something — movie magic at its finest. I also had the chance to go to Parrot Cay in Turks and Caicos a few years back and it’s still one of my fondest memories — for a number of reasons (which I’ll keep to myself).

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Any final tips for traveling in style?

I like to pack carry-on as much as I possibly can. I tend to wear my heaviest and bulkiest outfit on the plane (leaves room for packing in the suitcase). Plus, I have the option to take on and off sweaters and layers depending on the temperate inside the plane.

Enter now to win a pair of UGG for Men Huntley boots as modeled by Breslin! Be sure to read contest Terms & Conditions.