Travel Like a Boss: Business Trip Style

January 5th, 2015

Business travel can be a pain, but if you prepare properly, it doesn’t have to be.

Here are some tips to take the stress out of your next business trip.

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1. Wear your suit on the plane. Not only will you have a stylish flight and keep your suit from wrinkling, but the jacket’s interior pockets are designed for documents like passports and boarding passes. Dressing well for a flight can also have its perks when airline personnel “randomly” chose passengers to upgrade.

2. Wear your coat to save room in your carry-on. If it’s the right coat, like a classic overcoat or neutral trench, it will be the only coat you need for your entire trip. Before you get to security, store all your metals and accessories in the coat’s pockets, and simply take it off when you get to the checkpoint. The only things in the x-ray bin should be your coat and your shoes, which brings me to my next point…

3. Wear slip-on shoes. Penny loafers or chelsea boots are good options. And please, wear socks…for the sake of your feet, and your fellow travelers.

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4. Pack versatile items that you can wear several times throughout your trip. For example, every item you see here can be dressed-down for any off-the-clock activities that come up on your trip.

5. Get a wheeled luggage that’s small enough to qualify as a “carry-on”. I sometimes use a duffle bag as a carry-on but wheels just make life much easier, especially when wearing a suit.

6. Don’t bother with a belt, trousers with side-adjusters are perfect for breezing through security. Even if they’re made of metal (like the ones below) they’re such small clasps that they won’t set-off the metal detector.

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7. This might seem novice, but print your boarding pass ahead of time and store it in one of your jacket’s interior pockets. If you’re more up with the times, you could use your airline’s app to pull-up a digital boarding pass. That’s a real businessman move.

8. Keep the following items in the front pocket of your carry-on: headphones (for the music on your smartphone), foam earplugs (for screaming babies), an eye mask (to catch a nap before the big meeting), a bottle of water (so you don’t have to wait on the attendant), and something to read. That should have your basic necessities covered.

9. Once you arrive to your hotel, don’t live out of your bag. Settle-in asap by unpacking your luggage and hanging/storing your micro-wardrobe properly.

WesDB (1 of 1)
  • Khaki trench by Brooks Brothers Black Fleece ·
  • White Italian Collar Shirt ·
  • Hollywood Flannel Trousers by Articles of Style ·
  • “Remington” leather chelsea boots by Aldo ·
  • “Piazzale” wheeled leather suitcase by Maxwell Scott
  • · Blue Flannel Jacket Bespoke


Wool Flannel Jacket in Navy

Have any other air travel tips? Please share them in the comments!

Thanks, as always, for reading.

Yours in style,

Dan Trepanier

Shop Custom Menswear Made in America

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