How To Travel In Comfort... And Still Look Stylish
The last year of my life has been insane. I’m usually on a plane twice a week. I travel internationally maybe once a month. (I’m writing this from Tokyo, which is both fabulous and chilly.)
Travelling so much is equal parts a blessing and a jet-lagged curse. It also teaches you a few lessons along the way. Some of those lessons are hard-learned. The number of times I’ve had to be that guy who gets to the front of the security line and bends over in his skinny jeans to untie his lace-up boots… well, it took a while to sink in. Please, don’t be that person. Don’t wait until you get to the front of the line. Better yet, ditch the boots altogether.
If I had to summarise all of my travel learnings into a single, unassailable phrase, it’d be this: carry-on. If you’re only travelling for two to four days, there’s absolutely no need to take a check-in bag. This has a bunch of great knock-on effects.
First things first, you’re forced to edit. Good things happen when you edit.
One of my favourite things about taking only a carry-on is that it minimises my time in the airport. I only arrive at the airport 30 or 40 minutes before a flight. I go straight from security to boarding at the gate. After landing, I want to be able to get through the gate and out of the airport as quickly as possible… and not stand around a baggage carousel. Travel is already exhausting. The last thing you want to do is add airport time, just because you want a few extra looks.
I pack the night before. I try to choose six looks, total: one look that I’ll definitely wear, and one backup look, for every day of travel. I’ll usually start with denim. Maybe one pair of jeans in black and one in blue – because, honestly, nobody’s going to notice that you’re wearing the same black jeans twice.
I’ll keep my tops simple: basic colours like black, white and grey that I know I can mix and match. I’ll pack a suit that I can break up – think suit pants with a jacket, your blazer with a button-up shirt and denim. I’ll fold my suit right down since it’s easy enough to steam on arrival.
From there, I’ll pack one pair of light shoes, and wear my heavier shoes on the plane. Yes, I’m one of those people who’s not ashamed to take off my shoes on a plane. Feet get swollen; it happens.
Six interchangeable, versatile outfits can absolutely fit into carry-on luggage, and, for me, are more than enough for a short trip, even if I know that I’m going to be photographed.
When it comes to style in transit, I have two distinct schools of thought. Short flight? Two or three hours? I’ll rock whatever I feel most stylish in: jeans, boots, button-up, coat. Great. Any further than that – and definitely for any international flight – I wear sweats. And look, I know that people turn up their noses at sweats, but they can be done. We live in an age where sweats are very, very acceptable – ’90s style has come back, and, yes, we’re super fortunate to live in this era.
Wearing sweats in public, convincingly, is all about neutrals. I’ll make sure I’m wearing the nicest sweats I can get my hands on. When I was en route to Japan, I wore grey Yeezy sweatpants with a grey sweatshirt and a tee. Then I finished the look with a wool duster coat, white sneakers and white socks. Simple, chic colour palette. No messing around.
You might be wondering how I can recite this outfit so precisely. Well, it’s my travel uniform. I’ve worn a version of that outfit 50 times in the past year, if not 100. I’ve bought it in multiple colourways – tan, grey, navy. It looks wicked, quite honestly. And it’s as comfortable as anything. Once you strike upon that rare outfit that’s as comfortable as it is stylish, I advocate doubling or tripling down on it. Make it yours.
I know that style is important, but wearing a suit on a five-, six-, seven-hour flight is insanity. Being wildly uncomfortable isn’t worth any kind of momentary admiration, trust me.
Speaking of comfort, if you’re really ready to spoil yourself on a longer flight – and yes, this is an advanced move – try a sheet mask. After a certain number of hours in the air, your skin becomes massively dehydrated. After take-off, I put on a very heavy coat of moisturiser, and then I’ll wear a sheet mask. If you’re travelling in business or first, the rest of the plane will be none the wiser. Plus, when you arrive, you’ll look fresh as a daisy.
So: you’ve packed light, you’ve mastered style in transit – you only need three more key items.
Firstly, a mini-steamer. I view this as a necessity – lest you wish to play roulette with a hotel iron. It’s usually a lot quicker to use a steamer. They’re not perfect, but they’ll do the job if you need to get out of the hotel room in a hurry.
Number two: a lint roller. I don’t go anywhere without one. There’s always fibres lingering around from a scarf, or a plane blanket. I always leave one in my backpack.
Finally: mints. You never know which person is going to be sat next to you on a plane. You never know when they’ll have the urge to speak to you. You don’t ever want to turn to them, respond, and have the worst breath. So, have a mint ready to pop.
And, by the way, if you ever do have the urge to talk to a stranger next to you on a plane – maybe even at the start of a long-haul flight – I do have one other piece of advice: don’t. Please. Don’t.