There are several places on the internet which offer a number of guides on what to wear when travelling, so this will focus on business travel within the context of a three-day trip and a focus on travelling as light as possible.
Due to the baffling trend of keeping aeroplanes at a temperature cold enough to hang meat, my traditional casual travelling outfit looks something like this:
Long sleeved polo, stapresst strides and driving mocs. The long sleeves are for obvious comfort in the cold. These stapressts are made from an unpleasant manmade polyester material but they fit me well, arrive looking as decent as they left, and can be washed and dried rapidly in an emergency, obviously without the need for steam pressing. The shoes are comfortable and can slip off quickly at security if the airport doesn’t have a TSA Pre-check queue.
If I need to step up the formality a notch then out comes one of my trusty blazers. Menswear blogs are constantly extolling the virtues of a navy blazer but in this case the hype is well deserved, based largely on their versatility. I have too many blazers but the three I use the most are all dark blue, covering all seasons in hopsack wool, cotton, and linen. Adding either of these to an outfit can move it into unimpeachable business casual territory and if worn on the plane will save you some room in the case. Add a tie and you move up a notch in formality.
And on the subject of formality – context is everything so keep that in mind as you’re packing. Will odd jackets be enough or will suits be needed?
If day one is purely getting there, the polo shirt outfit above will work. If day one is travel and straight to business, then one of the blazer outfits could work. That means two more complete outfits – suits or jackets and strides – need to go in the case, which is just about doable.
Shoes are key as they take up so much space. If you have to bring a pair other than the ones you’re wearing to travel it will increase weight and volume and take a bite out of the space available for clothes. Try to plan your outfits around wearing only one pair of versatile shoes. I realise that violates the received wisdom of letting shoes ‘rest’ a day after wearing. Cap-toes, brogues or oxfords in black, brown or burgundy can work, or even dark suede if weather permits.
Example (business formal):
Travel in dark blue suit on day one. Pack grey and navy pinstripe suits for days two and three. Burgundy punch caps could work for all three days.
Example (business casual):
Travel in navy cotton blazer and tan chinos. Pack olive linen blazer with grey linen strides for day two, and khaki cotton blazer and dark jeans for day three. Choose from loafers, desert boots or Chelsea boots for all three outfits.
I have a heavy, spongey grey herringbone tweed jacket for frigid weather, and a grey Donegal jacket (pictured below) for cold weather. These are both versatile jackets that can be worn with dark jeans, heavy chinos or flannels.
I have a rust coloured cashmere blazer that can be worn with mid grey to dark grey flannels or even heavy winter white flannels.
Also worth considering is a ‘blazer suit’. I have a tobacco linen suit with patch pockets that can be split up so the jacket can be worn with odd trousers without looking orphaned. This kind of move can save you precious space in the rollaboard.
There are several things to consider but if you keep in mind context and versatility, and plan ahead so you’re not throwing things into the case while you’re ride to the airport is waiting in front of your house, you can not only get there, but also get through the business and get home – with style!