
The well-dressed man's guide to travelling in style
I have mixed feelings towards flying – on the one hand, I really dislike the airports, and hurtling through the sky in a confined, pressurised tube, breathing in stranger's flatulence. But I love the adventure – and the fact that (unless you're foolish enough to pay for Wi-Fi) nobody can reach you. I find my seat, set up a little playlist of movies, or I get my iPad out and illustrate, all while wearing the comfiest clothes in my wardrobe.
I've never understood why some people overthink their flight outfit. Unless you look suspicious, you can guarantee passport control don't care what you're wearing, nor do security, neither do the air stewards, the ground staff or any of your fellow travellers, for that matter. That said, there is a middle-ground between the suit I once wore and having one's dignity take a hefty blow by donning a onesie.
Prioritising comfort doesn't for a moment mean you have to sacrifice style and there is no need to travel in gym kit, athleisure or those knackered comfy shorts you wear around the house when you feel sick. Instead, simply tweak your thinking – elasticated or drawstring waists are better than belts and buttons when sitting for seven hours, luxe fabrics like cashmere will keep your temperature regulated while maintaining a luxurious, tactile feel. Minimising jewellery might be wise to avoid it irking as you adjust yourself mid-doze.
I have perfected two ensembles that I turn to flight and flight again.
Jim wears: Wool and cashmere blend hoodie, £295, Mr P.; Supima cotton t-shirt, £18, Marks & Spencer; Cotton blend twill trousers, £145, Mr P.; Suede trainers, £195, Russell & Bromley; Suitcase, Jim's own, Rimowa
Jim wears; Cotton flannel shirt, £175 (on sale for £88); cotton blend twill trousers, £145; both Mr. P; Supima cotton t-shirt, £18, Marks & Spencer; Suede shoes, £140, Birkenstock; Hitch Leather backpack, £625, Coach
A zip-through cashmere hoody like this one from Mr P is a joy to wear. Soft, tactile and the zip allows you to take it off without too much of a fight when in a close quarters. I did make the mistake of not wearing a T-shirt under one once, thinking extra skin-to-cashmere contact would be pleasant, but it was the hottest flight in the world, so I would highly recommend a good quality tee, such as the Supima Cotton options from M&S. Trousers like this linen/cotton blend from John Lewis will maintain the weightlessness of linen, but won't crease half as much, while the looser cut gives you the freedom to fidget. When it comes to footwear, Russell and Bromley's Woodale are minimal, sleek and easy to remove.
A Ralph Lauren flannel shirt will serve much the same purpose as a cashmere hoody, but where you lose the hood, you gain a chest pocket which I have found handy for my passport and earphones. These drawstring trousers from Mr P. have a touch of elastane, adding to comfort, and I'm such big advocate for these Birkenstock clogs. They're incredibly comfortable – and unlike their mule relatives, they have a heel so you won't hit the deck if you need to scurry for your gate.
When it comes to luggage, wheels are your friend! The number of times I've taken a holdall, only to find myself waiting at passport control with my phone in my right hand and the weight of everything else I'm taking in my left. It's a very dreary way to set your spine three inches off centre. Instead, I take the same leather backpack from Coach that has been my travel buddy for about a decade with just my passport, earphones, iPad, chargers and sunglasses while everything else goes in a wheely case, either to get checked in or come with me as hand luggage.

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