THE JOURNAL
Steve McQueen and Faye Dunaway in The Thomas Crown Affair (1968). Photograph by Alamy
On the internet today, people who perpetually mourn the decline of civilisation still post images suggesting that travel was once a more elegant affair. These honey-tinted photos are often lifted from mid-century ads and brochures: white-jacketed stewards pouring cocktails at cruising altitude, passengers stepping off ocean liners with polished shoes and perfect hair, monogrammed trunks stacked like postmodern sculptures. By contrast, modern travel can make you feel like livestock being herded through a chute. On X (formerly Twitter), someone is always complaining that nobody wears a blazer to the gate.
Yes, budget airlines have made lines longer and service more impersonal. At the same time, they’ve also made the experience vastly more accessible.
We travel, in part, to claim our capacity for attention and wonder. Things that may seem banal at home can take on a poetic quality when abroad, such an arched doorway or a fig tree spilling over a crumbling wall. However, this mindset doesn’t come magically upon arrival; it begins with preparation. The right set of clothes won’t guarantee a meaningful trip, but they can help make space for one. If travel teaches us to see, then dressing for the journey is the first step toward knowing how to look.
01. How to pack
The best packing advice I’ve ever received came from an Italian tailor who travels through the US several times a year for trunk shows. Alongside the clothes he wears, he also brings dozens of bespoke garments for fittings. His method is simple but effective: lay everything out on a bed, then stack it in layers, starting with dress shirts, followed by trousers and then knitwear. Once the stack is complete, fold it gently onto itself and place it into your suitcase. This technique helps minimise wrinkles by placing the most crease-prone items on the outside of the bundle, where they’re cushioned by the layers beneath. This avoids sharp folds and reduces pressure points during travel.
Tailored jackets, such as suits and sport coats, require special care because they’re built from multiple layers of haircloth, canvas and padding. These layers are carefully shaped through pad stitching and ironwork. If you cram one into your suitcase between your toiletry bag and a pair of shoes, you risk ruining that shaping.
To pack a jacket properly, turn one sleeve inside out and tuck one shoulder into the other. Place a rolled-up pair of socks under the shoulder seam to keep the shoulders from getting crushed. Then, while holding the jacket by the shoulders and hem, fold it in half. Gently open the lapels to prevent them from flattening in transit. Done correctly, your jacket should arrive with the same shape your tailor originally pressed into it.
Travel has changed, yes, but that doesn’t mean we have to surrender to shapeless clothes or overstuffed roller bags. With a little care, packing can be its own kind of intention-setting: a quiet ritual that says you’re choosing to move through the world with curiosity, not chaos.
02. Dress well and pack light
Assuming you’re headed somewhere hot, or at least hotter than where you are right now, you might want to re-familiarise yourself with your summer wardrobe. However, packing for a vacation isn’t just about staying cool. Also consider pieces that move seamlessly across settings: morning markets, museum afternoons and late-night shows. Your wardrobe should breathe, layer and adapt without bulk. While your exact needs will depend on the destination and itinerary, there are a few principles worth keeping in mind.
Start with the basics: a couple of T-shirts and your most comfortable pair of jeans or chinos. But elevate where you can. Camp-collar shirts and open-neck polos frame the face more elegantly than a standard crew-neck tee and can shift from casual to refined, depending on how they’re styled. Polos have the added benefit of being made from knitted fabrics, which tend to resist wrinkles better than woven styles. A pair of grey trousers is also worth including, particularly if you plan to dine somewhere more formal. Some trousers now come with elasticated waistbands, which provide sweatpants-level comfort while remaining polished when teamed with an untucked camp-collar shirt.
Bring a jacket with ample pocket space, such as an olive field jacket or a softly tailored navy sport coat. These provide lightweight layering for cool evenings or chilly museums, while also easing the load in your carry on. And even if locals dress casually, you don’t always have to – a tailored jacket can make an ordinary dinner feel more memorable.
Footwear should cover at least two categories: sneakers for long walks and sightseeing and loafers or suede chukkas for more polished outings. If you have room, a pair of dedicated room slippers can make unfamiliar hotels feel a little more like home.
If you’re headed somewhere with water, pack a pair of Orlebar Brown swim trunks, which are cut more like tailored shorts than beachwear. That means you can swim, towel off and, once dry, throw on a shirt and head to the hotel bar without changing.
Stick to a restrained colour palette – white, blue, brown and grey – and you’ll unlock an endless number of combinations by simply swapping things around. A white long-sleeve polo can be worn with swim trunks during the day, then with a navy sport coat and grey trousers for upscale restaurants. The best travel wardrobes don’t just keep you comfortable. They give you options without overpacking.
03. Consider fabric performance
When dressing for the heat, most people know about time-tested classics such as linen, seersucker and madras – fabrics long favoured in humid climates stretching from the Indian subcontinent to the American South. Linen shirts are especially well-suited for warm climates. Their flax fibres draw moisture from the skin and release it through the fabric’s surface, where it evaporates quickly. As for the wrinkles, think of them not as flaws but as part of linen’s easy, lived-in appeal.
However, fibre often plays a secondary role to a fabric’s weight and weave. Tropical wool, for example, is defined not by its origin but by how it’s made. These fabrics use high-twist yarns, spun with extra tension to create a more resilient thread. Weavers then construct an open-weave cloth that is opaque yet breathable, allowing body heat to escape and air to circulate. A tropical wool shirt can feel cooler than a densely woven linen version. Thanks to its natural springiness, tropical wool also resists wrinkles, making it an excellent choice for travel.
To gauge a fabric’s breathability, simply hold it to the light – visible permeability often signals cooling performance. Consider which properties best suit your itinerary: breathability for hot afternoons, moisture-wicking for long walks, or wrinkle resistance for pieces you’ll wear straight from your suitcase. No fabric covers every base, but the right mix can make all the difference.
Clothes alone won’t transform a trip, but they can prepare you to meet the day with attention. And that, more than any amenity, is what makes these journeys – and a welcome winter break – meaningful.
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