How I Travel
I travel a lot for both work and pleasure, and in my time traveling, I’ve learned one cardinal rule: pack as light as possible. These days, I try to only bring a carry-on and one personal item (my briefcase, which always contains my laptop and some reading material). In my carry-on is a small set of clothes – two grey trousers, four light blue or white shirts, one navy sweater, and a sport coat. I find that this is enough to get me through a few days before having to do laundry, especially since we’re not also counting the clothes I’m wearing onto the plane. Other things, such as shaving razors, soaps, and shampoos, can always be bought at the destination.
I like bringing a few superfluous things that make the trip more pleasant, however. For one, instead of wearing a sport coat onto the plane, I use a travel jacket I bought from Herno. It looks a bit like this one from Woolrich, but it has a hidden zippered pocket and no epaulets. Zippered and snap button pockets are useful for making sure things don’t accidentally slip out when you take off your jacket and carelessly carry it around. The idea of being in a foreign country and suddenly realizing that you’ve lost your papers, credit cards, and money just seems really, really bad. So I wear a travel jacket. Woolrich and Boggi have one this season (you may need to call Boggi’s actual stores to order), but you could also just wear anything lightweight and of a similar design. Just search around for “field jackets.”
I also use a travel wallet. These help keep my important documents and cards all in one place – passport, green card, identification papers, credit cards, health insurance card, boarding pass, and little slips of paper on which I’ve jotted down my hotel, flight, and train information. Having them all in one place gives me a peace of mind and some convenience. Many airports these days have multiple checkpoints where you have to show your papers to some official, so it’s convenient to have them ready and on hand. My travel wallet is by Chester Mox, who is running a Father’s Day promotion until Thursday, but you can also find some nice ones by Saddleback, Aspinal of London, Filson, and Tanner Goods.
There are a few other things I find helpful. Sleeping pills can get you through a long flight, but they also leave you feeling drugged. So instead, I eat Tianwang Buxin Wan, an all-natural, root-based pill that relaxes me enough to go sleep. It’s great on the plane and for when I’m trying to recover from jet lag. I also wear Bose noise cancelling headphones that a friend generously gifted me, and either soft suede driving shoes or a pair of canvas plimsolls. Feet tend to swell up during flight, which makes wearing hard bottom leather shoes extremely uncomfortable. Even if you take off your shoes, your feet can swell so much that they can be hard to put back in. Should you find yourself in such a situation, I recommend using my credit card trick.
And that’s basically how I travel - a carry on and my briefcase, along with a travel jacket, travel wallet, pair of soft shoes, and some things to help me go to sleep. These are enough to get me through fifteen to twenty hour travel schedules and still land in reasonably good form. 
(Pictured above: My travel jacket, travel wallet, and laptop at JFK airport)

How I Travel

I travel a lot for both work and pleasure, and in my time traveling, I’ve learned one cardinal rule: pack as light as possible. These days, I try to only bring a carry-on and one personal item (my briefcase, which always contains my laptop and some reading material). In my carry-on is a small set of clothes – two grey trousers, four light blue or white shirts, one navy sweater, and a sport coat. I find that this is enough to get me through a few days before having to do laundry, especially since we’re not also counting the clothes I’m wearing onto the plane. Other things, such as shaving razors, soaps, and shampoos, can always be bought at the destination.

I like bringing a few superfluous things that make the trip more pleasant, however. For one, instead of wearing a sport coat onto the plane, I use a travel jacket I bought from Herno. It looks a bit like this one from Woolrich, but it has a hidden zippered pocket and no epaulets. Zippered and snap button pockets are useful for making sure things don’t accidentally slip out when you take off your jacket and carelessly carry it around. The idea of being in a foreign country and suddenly realizing that you’ve lost your papers, credit cards, and money just seems really, really bad. So I wear a travel jacket. Woolrich and Boggi have one this season (you may need to call Boggi’s actual stores to order), but you could also just wear anything lightweight and of a similar design. Just search around for “field jackets.”

I also use a travel wallet. These help keep my important documents and cards all in one place – passport, green card, identification papers, credit cards, health insurance card, boarding pass, and little slips of paper on which I’ve jotted down my hotel, flight, and train information. Having them all in one place gives me a peace of mind and some convenience. Many airports these days have multiple checkpoints where you have to show your papers to some official, so it’s convenient to have them ready and on hand. My travel wallet is by Chester Mox, who is running a Father’s Day promotion until Thursday, but you can also find some nice ones by Saddleback, Aspinal of London, Filson, and Tanner Goods.

There are a few other things I find helpful. Sleeping pills can get you through a long flight, but they also leave you feeling drugged. So instead, I eat Tianwang Buxin Wan, an all-natural, root-based pill that relaxes me enough to go sleep. It’s great on the plane and for when I’m trying to recover from jet lag. I also wear Bose noise cancelling headphones that a friend generously gifted me, and either soft suede driving shoes or a pair of canvas plimsolls. Feet tend to swell up during flight, which makes wearing hard bottom leather shoes extremely uncomfortable. Even if you take off your shoes, your feet can swell so much that they can be hard to put back in. Should you find yourself in such a situation, I recommend using my credit card trick.

And that’s basically how I travel - a carry on and my briefcase, along with a travel jacket, travel wallet, pair of soft shoes, and some things to help me go to sleep. These are enough to get me through fifteen to twenty hour travel schedules and still land in reasonably good form. 

(Pictured above: My travel jacket, travel wallet, and laptop at JFK airport)