For a winter city break or a day at the Christmas markets, wear a thin base layer under your clothes and soft cotton boxer briefs or trunks with legs long enough to stay put while you walk. Pack one thermal set for the coldest evening outdoors and one pair of quick-drying underwear per day, and you can go from frosty squares to warm cafés without feeling either frozen or overheated.
Why winter city trips are tricky to dress for
A winter city break swings between two climates. Outside you stand still for long stretches: queuing for mulled wine, watching a skating rink, waiting for a tram. Inside, museums, shops and trains are heated, and you are suddenly carrying a coat, a scarf and a bag.
That stop-start rhythm is what makes underwear matter. The layer closest to your skin should:
- hold warmth when you are standing on cold cobbles for an hour,
- let warmth out again when you step into a crowded heated hall,
- stay in place over 15,000 steps of sightseeing,
- pack small, because a weekend bag fills up fast with jumpers.
Start with a base layer you can remove
The simplest trick for market evenings is a thin thermal top and long johns under your normal outfit. Because it sits close to the body, it adds warmth without the bulk of a second jumper, and your jeans or chinos still fit.
The Arjen Kroos thermal set comes as a long sleeve top plus long johns and in two weights. The fleece lined colours (92% polyester, 8% spandex with a soft fleece lining) are the ones for a long, cold evening outdoors. The plain Black and Grey versions (80% rayon, 14% acrylic, 6% spandex) are lighter and more breathable, which suits a day that mixes walking outside with time in heated museums.
A practical tip: wear the long johns on the coldest market night and the top on its own on milder days. Rolled up, both pieces take less space in a bag than one knitted jumper.
The best cuts for a day of walking
Old towns mean cobblestones, stairs up to viewpoints and long loops between stalls. Cuts with a leg are the most reliable choice here, because a short leg that creeps up gets annoying by the afternoon.
| Cut | Best for | What to look for |
|---|---|---|
| Boxer briefs | All-day sightseeing | Soft cotton blend, a waistband that does not dig in under a belt |
| Trunks | Jeans and slim trousers | Mid-thigh leg that grips, flat seams |
| Long leg boxer briefs | Long walks, thicker thighs | Anti-roll hem, quick-drying fabric |
| Briefs | Evenings, warm hotel rooms | Tag-free, elastic waistband |
The cotton boxer brief (95% cotton, 5% spandex) has a 3D pouch and a stretch waistband knit with spandex, which spreads pressure instead of cutting in when you add a belt and a heavy coat. The breathable cotton trunks (93.2% combed cotton, 6.8% spandex) have a 4 cm wide soft waistband, flatlock seams and a mid-thigh leg that is cut to grip rather than bunch.
Cotton or quick-dry? Packing for a short trip
Cotton feels familiar and cosy, and it is the natural pick for cold days that you mostly spend walking at an easy pace. Its weak spot is drying time. If you plan to wash a pair in the hotel sink, a synthetic fabric dries much faster overnight.
The long leg boxer briefs in plain ice silk (88% polyamide, 12% spandex) are light, silky and dry quickly, with a 3D U-pouch and a longer leg finished with an anti-roll hem. They are a good second type to pack next to cotton: wear them on the day with the most walking, rinse them in the evening and they are ready again by morning. Our guide to hand washing underwear while travelling explains the towel-roll trick that speeds this up.
A simple packing list for three nights
For a typical long weekend in a market city, this fits easily into cabin luggage:
- 3 pairs of cotton boxer briefs or trunks for the walking days,
- 1 pair of quick-drying long leg boxer briefs as a spare you can wash,
- 1 pair of tag-free briefs for the evening and the trip home,
- 1 thermal set (fleece lined if the forecast is below freezing),
- warm socks, a hat and gloves, which do more for comfort than an extra jumper.
Planning a longer trip? Our travel underwear packing guide covers how many pairs to bring for one or two weeks.
Layering for the market evening
Christmas markets are at their best after dark, which is also when the temperature drops. Build the outfit from the skin out:
- Underwear: boxer briefs or trunks with a leg.
- Base layer: thermal top and long johns, close-fitting so nothing bunches.
- Middle: shirt or knit, then jeans, chinos or wool trousers.
- Outer: a coat you can open when you step into a warm bar.
If you go on to dinner, you can slip into the restroom and take off the thermal top while keeping the long johns on. For snow-heavy destinations and mountain trips, see our cold weather layering guide.
Frequently asked questions
What underwear is best for walking around a city all day in winter?
Boxer briefs or trunks with a leg that stays in place, in a soft cotton blend. Add a thin thermal layer on top if you will spend long periods standing outside.
Should I wear thermal underwear to a Christmas market?
Yes on cold evenings. A close-fitting thermal top and long johns add warmth under normal clothes without making your trousers feel tight. Pick fleece lined for frosty nights and the lighter version for milder days.
How many pairs of underwear do I need for a weekend city break?
One pair per day plus one spare. A quick-drying pair is useful as the spare because you can rinse it in the hotel and wear it again.
Is cotton or synthetic underwear better for winter travel?
Both have a place. Cotton feels soft and cosy for relaxed days, while polyamide blends dry faster after a hand wash and suit busier walking days.
Get ready for your winter trip
Browse our men's cotton underwear for cosy walking days, our boxer briefs for cuts that stay put, and our ice silk underwear for quick-drying spares. Every order ships in discreet packaging.
