Packing for a holiday or trip always starts the same way for most guys. We obsess over the right sunglasses, the perfect pair of shorts, the softest t-shirts. Yet the single most important piece of clothing, the very first layer that touches your skin the moment you step out of bed, barely gets a second thought. That is a mistake. The right underwear can turn a long flight into pure comfort or a sticky, irritated mess. The wrong choice can leave you shifting in your seat for hours, dealing with fabric that rides up, or worse, that unmistakable chafe between the thighs after a day of walking. I have been there more times than I care to admit, and as someone who genuinely loves good underwear, I have learned exactly what works and what does not.
After years of testing every style, fabric and fit on flights, road trips, beach days and city breaks, I know this much: one pair will never cover every situation. You need a small, carefully chosen selection that matches the activity. Below is the practical breakdown I use every single time I pack, written from the perspective of a man who appreciates how underwear should feel against the body, how it should support, breathe and still look good when the outer layers come off.
Flying and long distances: the classic slip
Nothing tests underwear quite like an eight-hour flight in a narrow economy seat. Your legs are pressed together, the seatbelt digs in, and every tiny movement is magnified. In that situation the classic slip, or brief, is still the undisputed champion. A well-cut Calvin Klein style brief keeps everything neatly contained without any excess fabric to bunch or crawl.
The beauty of a good brief is the complete lack of leg openings that can roll. There is simply nowhere for the fabric to go. The pouch sits snug, offering solid support so nothing shifts around while you try to sleep or watch a movie. When you finally stand up after landing, the waistband has not dug painful marks into your hips and the front has stayed put. That alone is worth the price of a quality pair.
I always pack two or three solid briefs for any flight longer than three hours. They take up almost no space in a carry-on and can be washed in a hotel sink if needed. The only real downside appears once you leave the airport. If you immediately start walking long distances in heat, the lack of any fabric between the thighs can lead to friction. That is why briefs are perfect for the journey itself but not necessarily for the days that follow.
A small tip from personal experience: choose a brief with a soft, wide waistband. Thin elastic that cuts in after two hours will ruin the whole point of choosing comfort. Modal or a high-quality cotton-elastane blend feels almost invisible against the skin while still holding its shape.
Long car rides and active days: the hipster or trunk
Once the plane is behind you and the real trip begins, the needs change. Long drives, city exploration on foot, hiking trails or simply a day of moving from one place to another call for something with a short leg. The modern trunk or hipster style, especially the athletic versions from Nike or similar performance brands, solves the biggest problem briefs leave behind: thigh friction.
Those few centimetres of fabric that cover the top of the legs act as a buffer. Every time your thighs move against each other while walking or shifting gears in the car, the material takes the rub instead of your skin. On a hot day that difference is everything. I have finished entire walking tours in a good pair of trunks without a single red mark, something that used to be impossible in regular briefs.
Performance fabrics make these styles even better. Moisture-wicking material pulls sweat away from the body and dries quickly, so you stay comfortable even when the temperature climbs. The fit is usually more athletic, meaning the pouch supports without compressing and the leg openings stay in place instead of riding up. A well-designed trunk moves with you rather than fighting every step.
The only caution is quality. Cheap trunks with weak elastic will still crawl upward after an hour of sitting. Invest in pairs that keep their shape. I keep a rotation of black and navy trunks specifically for travel because they hide any accidental stains and look clean under almost any pair of shorts.
Warm destinations and sun days: airy bikini briefs and thongs
Arrive somewhere tropical and the rules change again. When the air is thick with heat and humidity, less fabric is simply better. This is where the smallest styles come into their own: low-rise bikini briefs and proper men’s thongs.
A well-made thong or micro bikini brief removes almost every barrier between your skin and the air. Under thin linen trousers or lightweight swim shorts there is nothing to create bulk or visible lines. The sensation is free and surprisingly comfortable once you get used to it. Many guys assume thongs are only for the bedroom, yet on a scorching beach day they are often the most practical choice available.
Ventilation is the real advantage. Heat and moisture have nowhere to build up, which means far less chance of that sticky, uncomfortable feeling that can ruin an afternoon. Packing is also effortless. A handful of these styles weighs almost nothing and folds into a space smaller than a pair of socks.
Not every man is immediately comfortable with the feeling of a thong. The first few wears can feel unusual, but most people adapt within a day or two. If you are new to the style, start with a slightly wider side strap rather than the thinnest possible string. The support is still excellent and the adjustment period is shorter.
One honest limitation remains: intense activity. Running or long hikes in a thong offer almost no protection against thigh rub. Save these for beach days, poolside lounging and relaxed evenings when movement is limited.
Extra packing tips from someone who lives in good underwear
Material choice matters more than most men realise. Pure cotton feels wonderful on a calm day at home, yet it holds moisture like a sponge. Once it gets damp from sweat it stays damp, and that is when irritation begins. For any trip that involves heat or activity I switch entirely to modal, bamboo or technical microfibre. These fabrics feel softer than cotton, dry in a fraction of the time and keep their shape wash after wash.
The hotel sink method is pure gold. Quick-drying trunks or thin briefs can be rinsed with a drop of shampoo in the evening, rolled tightly in a towel to remove excess water, and left to air overnight. By morning they are ready to wear again. This simple habit means you can pack fewer pairs without ever running short.
My personal packing formula is straightforward: one clean pair for every day of the trip plus two or three extras. A seven-day holiday gets nine or ten pairs. The extras cover unexpected weather, spontaneous swimming or simply the desire to change after a long afternoon. It is better to have them and not need them than the opposite.
Colour and style also deserve a moment of thought. Dark colours hide any marks and look sharper under light summer clothing. A mix of solid blacks, deep navies and one or two slightly bolder patterns keeps things interesting without drawing unwanted attention through thin fabric.
Finally, never underestimate the psychological side. Knowing you are wearing something that fits perfectly, supports properly and feels good against your skin changes the entire day. You walk differently. You sit more comfortably. You stop thinking about your underwear and simply enjoy the trip. That quiet confidence is the real reason I care so much about what goes into the suitcase first.
Putting it all together
No single style of underwear can handle every part of a holiday. The smart approach is to pack with intention. A couple of classic briefs for the flights keep you supported and free of riding fabric. A few pairs of performance trunks protect against chafe during long days on the move. A small selection of ultra-light bikini briefs or thongs gives you maximum airflow once the heat arrives.
Treat your underwear the same way you treat the rest of your travel wardrobe: choose quality, match the piece to the activity, and never settle for something that merely “does the job.” When the first layer feels this good, everything that follows feels better too. Pack deliberately, wear with pleasure, and enjoy the journey from the skin outward.
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