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.


    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.


    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.


    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)

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

    Thanks, as always, for reading.

    Yours in style,

    Dan Trepanier


    Photography by Alex Crawford. Styling by Dan Trepanier. Modeling by Will Howe

    • Ian

      Apply for Global Entry, it costs $100 and make the whole security process a breeze.

      • Dave

        yup. Global Entry or TSA Pre-Check are well worth the sign up fee. (TSA Pre-Check is $85, and lasts for 5 years) Keep your coat and shoes on, and get access to the super short line. I’ve gone from curb to gate in less than 5 minutes on all my recent trips.

    • JoeFromTexas

      Always wear your cowboy boots on the plane, because they’re too big to fit into your luggage. (What do you mean you’re not taking your cowboy boot with you everywhere you go?!). I like to make sure I’m wearing pants with suspender buttons when I fly so that I don’t have to deal with a belt (and suspenders obviously). Plus I have all my typical everyday carry in an outside pocket of my brief/laptop bag – I put a credit card and ID in my shirt pocket and ticket and passport in my blazer pocket.

    • Brendan Ruane

      Often, I travel wearing my jacket as a sportcoat with dark denim. Jeans are much heavier than the matching suit pants and so it lightens your bag while being more practical for longer flights. The suit pants are easy to pack in with my other clothes.

    • tommyjohn_45

      One thing I have learned (as odd as it may be), is security’s postive response to bold socks. I know this has been a topic of great debate, but for those who enjoy wearing unique socks, security guards seem to really get a kick (pun intended) out if when you go through with your shoes off. Can’t tell you how many times a great conversation has started over socks. Not to mention a much breezier experience.

    • Jeanscuffed

      I’m gonna sound weird (hopefully someone backs me on this) but I love going to airports, even to pick up someone. Many people are unaware that an airport is also a great place to people watch. Fashion is everywhere and it’s great to see different people and their fashion choices from all over. Of course traveling is great but sitting there waiting to pick up someone is therapeutic to me. It’s like reading a live magazine.

      • tommyjohn_45

        Great perspective. I agree, l love all aspects of going to the airport (aside from the 3-4am wake ups). At international air ports, you can definitely take in a wide range of styles and personalities.

        • AdamE

          People watching makes the time waiting for luggage to arrive (should you be flying with checked baggage) fly (or the wait for your flight, should you follow all of the pro-tips mentioned and breeze through security…).

          I don’t mind going to pick people up, as long as the flights aren’t mega delayed, or it’s not at obscene times (my wife has a bad habit of, when she flies south with friends and not me, trying to stretch as much beach time as possible, so arriving on the return flight at ungodly hours (for those of us who weren’t on vacation…))…

          I’ll also fully admit, when traveling with someone, that we’ve done hypothetical narration of conversations between people you see in the terminal (i.e. like they do in restaurants in the movie Date Night w/ Steve Carrell and Tina Fey)…

    • cam

      a few more tips..
      – be sure to sign up for rewards programs if you travel frequently. you will be treated better by the various staffs.
      – i always buy a local paper when i arrive in a city. it makes you appear as a local and therefore treated better. also good to learn of any happenings in the city of course.
      – i would also suggest hand sanitizer and Emergen-C when traveling

      • Dan Trepanier

        Cam’s obviously a pro.

      • tommyjohn_45

        Solid points. I definitely agree with you on the rewards program. Recently I have been traveling for work twice a month, using the same airline. Needless to say, I’ve saved up a few free personal flights while my company pays for all my airfare!

    • James Wong

      Great post, however I’m going on a 10+ hour flight from Uk to Singapore for a wedding next week and I don’t think my suit will be too comfy for that duration. Instead, I’m going to pack it in the way that AoS has shown in a previous post.

    • Antonio López

      Excelent post Dan, I’ve been following your blog for a while and It have really change my attitude about style and clothes. Keep up the good work.

      • Dan Trepanier

        Thanks Antonio! Appreciate your support. We have some great things coming up, stay tuned :)

    • Geezer

      The one thing I would advise against is traveling in flannel. Though I could not live without the fabric, it does tend to wrinkle quite a bit and should be rested for two days between wearings making it not overly ideal for travel — though the look is boss ;)

      • Dan Trepanier

        Good point, as flannel can also get warm. One thing I left out, I usually remove my jacket and fold it neatly in the overhead bin, if there’s room. Cheers “Geezer”.

    • Todd Ruhnau

      Nice advice. Wearing a blazer in the airport really makes security a lot easier. I always choose to look put together while flying because honestly you never know who you’re going to sit by. Whether it be someone in a similar line of work or just someone worth leaving a good impression on.

      • Dan Trepanier

        I once bumped into the reverend Al Sharpton in an airport, wearing one of his signature three piece suits standing stoically by the gate. He looks at me in my double-breasted hopsack number, sizes me up, and says “nice suit”. I reply “same to you”. Then one of our readers recognized me (and him, of course) and took a picture of the two of us together, and we chatted for fifteen minutes about suits, shoes, and politics. Point being…you never know you you’re going to meet. Thanks Todd!

        • Jeanscuffed

          At first I read it as YOU were wearing one of his signature suits lol. I was confused like A. I didn’t know Al had a suit line and B. Why would YOU be wearing one of his suits lol

    • Diavee

      A lot of airlines don’t allow you to carry water with you, right?

      • herb

        Just have to purchase past security.

      • JBells

        I usually bring an empty refillable bottle with me. Once I pass security I can fill it for free.

        • Dan Trepanier


      • AdamE

        As they said, either an empty reusable one, or buy one after security.

        Also, any liquid toiletries should be in a plastic baggie that is easily accessible in your luggage (if you’re using just a carry-on, otherwise, stowed in the Dopp kit in your checked luggage), since often that has to be out of the luggage and in the bin as well before being scanned. Also make sure electronics (i.e. laptop/tablet if traveling with such) are charged and accessible, since they often like those out and in the bin for security, and may require being turned on to show that they are not explosive devices… (never used to be an issue, but since 9/11 I would say 95% of the times I’ve gone through airport security I’ve had to pull them out of my carry-on, and probably at least 50% of the time I’ve had to turn them on to demonstrate that they are what they look like they are…).