The best travelling day outfits are, essentially, what is most comfortable to wear, what is most functional and would be the least likely to wrinkle. Depending upon the length of the flight, as well as the number of stopovers, the constant traveller should dress in layers, in case the scheduled flight is delayed, or the weather turns nasty in stop-over cities or transfer points. Any hand-held gaming systems, cell phones and laptops should be on your body, or in your carry on luggage, so that it will be handy to you in case of either delays, inclement weather, or for any other emergency reasons.
The clothes that we wear travelling while on business, however, must meet the standards of the company that we represent while travelling. However, the casual traveller should not fear wearing a pair of shorts under a skirt or dress for women, and men can wear pants that have zippered cut-offs that transform the pants into shorts, if the destination is a warmer climate, like Cuba or Hawaii.
Leisure suits, infamously parodied by Frank Zappa’s “Bobby Brown” (“I got me a leisure suit. I jingle my change, but I’m still kind of cute”), have extra pockets for storing the smaller and more private accessories that make for more comfortable travel. However, leaving that suit jacket hung over the back of your chair while you slowly fall asleep waiting for that flight number, or boarding number, to be called can result in the loss of your jacket and all that was in it, since most airports have their own thieves lying in wait for just such happenstances. One of the best inventions for the constant traveller is the purse/wallet, the kind that opens up into many different compartments, and have shoulder straps for safety. These fold up, unisexual wallet sized purses have zipped-up compartments for smaller things, like change, batteries, etc., and compartments for easy access to passports, tickets, money and other
The old stand-bye, jeans and tee-shirt, sweater and jacket, with a few comfortable changes of shirt and underwear in the carry-on baggage is always a comfortable and durable outfit. Maybe not quite classy enough for the VIP waiting rooms, first class service or business meetings, but very comfortable. And, wearing jeans gives the added bonus of being able to sit, or lie down on the floor a not so miserable thing to do when short waits turn long.
Also depending upon the weather, the clothes that you wear travelling should be more aligned to the climes of your destination, not your origination. Living in Florida, you may want to wear something more than a light shirt, shorts and sandals when heading to British Columbia in the winter for a skiing holiday. Before departing home for the airport, check the weather forecasts for any and all stopover points, and your final destination. This information tells you how warmly to dress, weather or not you need any rain gear handy, and what types of footwear to wear, and to keep in your carry on luggage.
Leaving from Ottawa, flying to Cuba in the winter, the constant traveller may need to wear warm clothes to get to the airport, but once inside the airport, they are not likely to need the warm clothing until they return from their trip. Bringing any more warm clothing than what is necessary for the trip to the airport is a complete waste of storage space, room that those cigars and Che Guevara memorabilia could have taken up on your way home.
The best travelling day outfits are the ones that you can wear once you reach your destination. You should be able to get off of the plane, and be comfortable with what you have on, not needing to change on order to be comfortable. This makes for running to your hotel the minute you land not so much a necessity. You can have a leisurely time getting to know the area that you are staying at, while travelling to your hotel from the airport. Remember, the best travelling day outfits are not just for while you are on the airplane.