Tips for a Stylish & Stress-Free Flight

March 2nd, 2013

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Whether you’re flying for business or a swanky Spring vacation, air travel can be a pain. But if you prepare properly, it doesn’t have to be.

Here’s some tips to take the stress out of your trip through the airport:

1. Avoid checking luggage. A carry-on will speed up the process and avoid any stress related to lost or damaged baggage, not to mention save you a little $ in checking fees. If the trip is less than a week, you should be able to pack (and wear) versatile enough pieces to get by on one medium-sized duffle bag.

2. Have your boarding pass ready. The longest wait in the airport is usually to print your boarding pass. If you’re not checking bags, you can skip this completely. Print it out beforehand, or use the fancy barcode scan on your smartphone.

3. Before you leave the house, get metal-detector-ready. This means storing your belt, watch, phone, keys, wallet, etc. at the top of your carry-on. No sense putting something on that you will inevitably have to take off. Keep only your boarding pass, passport, and one credit card in your pocket, and feel free to accessorize once you’ve reached the gate.

4. Wear slip-on loafers! And please, wear socks…for the sake of your feet, and your fellow travelers.


5. If you’re bringing a suit, wear it on the plane. Not only will you look stylish in-flight, but the jacket’s interior pockets are designed for passports and passess, and, most importantly, it’s better for the life of the suit than squashing it into your carry-on.

6. Wear a polo shirt, for comfort. This one has a deep placket and button-down collar, perfect for under a suit. Have a lightweight sweater close-by too, for those unpredictable cabin temperatures. Make it a cardigan, not a pull-over – it’s much easier and more graceful to add or remove.

7. Your carry-on goes under the seat in front of you, to leave room for your neatly-folded jacket in the overhead compartment.

8. Once you arrive to your destination, settle-in asap and hang/store your wardrobe properly. Don’t forget, most hotels have an iron and board in the room. If not, you can always get the shower steam going.

Have a great trip! Next up: a series on what to bring and how to pack it.


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


Thanks for reading.

Yours in style,



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  • Fabio d’attimis

    I really liked this post… Will you make something similar to this?

  • Sam

    If for some reason you pack your suit jacket, turn it inside out before folding it. It will protect it from wrinkling. Then, wrap it in dry cleaning plastic and place it at the bottom of the suitcase/bag with shirts on top. Placing it on the bottom will help keep it from moving around while in transit.

  • Thomas J. Hill

    First, a medium size duffel bag is not a carry on – they are far too large for the overhead bins, and you will definitely anger your traveling companions as you crack them on the head with the thing. Second, having boarding pass and ID ready, wearing easy-to-remove clothing, and being prepared for the check in lines is just good common sense. The TSA lines are not new, and should not be a surprise to anyone who has traveled in the last 10 years. Bring soft foam earplugs and an eye mask if you intend to nap on the plane. Be prepared for other travelers to not be prepared, so don’t get upset by it. Do your thing and do it well, and you will have a less stressful flight. Most importantly – show up at the airport early, not just “on time.” Bring a book and read while you wait at the gate. This is far better than rushing to get to a flight!

  • Glenn Boskey

    Why do you guys insist on making this kid look like the Uni-Bomber in every shoot?

    • Dan Trepanier

      We don’t make any kids do anything. Funny joke though.

  • Chris Campbell

    If you are packing your shoes in your luggage use shoe trees to stop them getting warped, or stuff with socks.

    And don’t fly Ryanair if dressing up for flying is your thing.

  • Edwin C

    Great info! I’m flying into NYC Wednesday so this really helps! Hurry with the second post so I can why to pack for the NYC cold, I’m from south fl.

  • Ella

    looking dapper Towni

  • Adyna

    9. Keep a lucky special thing in your pocket..always…this can be a scarf, a stone (in my case:)..whatever makes you feel good. Everybody, Have a safe and easy flight!

  • Paul

    Wearing the nicest outfit you bring makes perfect sense until you realize you’re sitting underneath a cocktail precariously balanced on a moving table and next to a person getting greener and greener due to the turbulence. I wear the jacket, pack the pants. Good call on the polo.

    • joe

      Funny – I never had getting thrown up on as a major concern during air travel. Maybe I don’t fly enough to realize the danger this really poses.

    • Dan Trepanier

      “how good is a jewel that is too precious?”

      • Paul

        Probably about as good as showing up to a Saturday wedding with a Friday stain on your pants.

        • Dan Trepanier

          I see what you’re saying. I guess I don’t usually worry about staining my clothes. Either way, I’d suggest packing a second pair of pants that works with the jacket.


    • Alan

      That rings true to me too. I quite like a pair of cargos when travelling, but you can’t really get upgraded on Eurostar sadly.

  • http://undefined Alex

    I second what DK said below:

    “Be extremely polite when dealing with the people at the check-in booth I’ve been upgraded to 1st class in the past.”

    I will also add that I always wear my nicest clothes that I’m bringing on the trip on the plane, in part as the boys say to keep the outfit from getting wrinkled, but also becuase dressing really nice has gotten me upgrades to 1st class on more than one occasion. People dress so lousy for air travel that the crew/front gate people are really taken aback by someone up the nines for air flight. Remember, our grandfathers used to dress up for air travel, it used to be a special privelage.

    Lastly, if you wear a hat(I wear a fedora often), wear it onto the plane and you can place it near your feet or on your lap after you’re sitting.

  • Joe

    I like to store metal pocket stuff (keys, wallet, money clip, change, etc), save for an ID and a credit card, in a crown royal bag and put it in a side pocket somewhere (coat, duffel, laptop bag). I suppose that means I carry a purse when I fly, and I’m ok with that.

    • John

      Great idea! I usually do this with a ziplock, but the Crown bag (or any other drawstring pouch) is genius!

      Solid info here, TSB gang. Thanks!

  • A.

    Very cool outfit. What cloth is the suit?

  • http://undefined TimL

    Great tip, thanks.

    I seen a nice timberland leather bag just like the one shown for about $50 today. I think I’m going back to get it with a 20% off coupon tonight.

  • SAJ

    Nice post, heads up: I think link in #6 is broken?

    PS any recommendations for quality bags that may be a stepping stone up to premium bags (i.e. Frank Clegg). Talking to a recent college grad who wouldn’t be able to afford a $900 bag now.. I figure thrifting, but maybe you have mid or lower tier bags to buy new, that still look elegant.


  • Jess

    Excellent tips. Im flying tomorrow morning so its nice to have a refresher before I go.

  • Miguel

    Very nice article, sick outfit.

  • Alan

    Interesting post. It may be worth pointing out that, in Europe at least, there are some some airlines who have lower maximum dimensions for bags – 55cm x 40cm x 20cm is the limit in some cases, which rules out most specially designed ‘Cabin’ bags.

  • Pete

    Sick loafers, what are they?

    • Dan Trepanier

      Ralph Lauren suede penny loafs

  • http://undefined Will

    I really like the look of that button down polo shirt. Are there any other examples of that style of polo outside BB?

  • Scott Elias

    Great post! What iPhone case/cover is that? I love the leather look.

  • Ace F

    Thanks for the tip.
    This is very timely here because summer is almost here in the Philippines.

    PS. Townsend looks very classy in any suit. Its like its very natural for him to wear those.

  • Rob A

    Tetris is the name of the game. I like to roll my clothing after folding it to save space in my luggage.

  • DK

    Be extremely polite when dealing with the people at the check-in booth I’ve been upgraded to 1st class in the past.

  • Mike

    Which brand is this duffle bag?